March 14, 2022 • 49 mins
September 1997. Bob’s wiretap evidence culminates in two major trials and the downfall of a mafia kingpin. But was it all worth it for Bob?
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Episode Transcript
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Speaker 1 (00:15):
Pushkin previously on Deep Cover.
Speaker 2 (00:45):
Bob Cooley fled Chicago in November of nineteen eighty nine.
Bob's life as he knew it was over. He had
rejected the witness protection program and instead opted to improvise.
He took on a new identity and planned to hide
out Meanwhile, back in Chicago, Bob's efforts resulted in charges
(01:05):
against at least two dozen men, lawyers, judges, cops, and politicians.
Chief among them was Pat Marcy, who effectively ran the
first ward, the Mob's political stronghold.
Speaker 3 (01:17):
So this is like a not just a cascade, it's
an earthquake on Chicago politics. This is a staggering revelation
involving a lawyer. Virtually no one outside of a circle
of real insiders knew at all.
Speaker 2 (01:35):
Bob's days as a covert operative may have been over,
but he still had work to do. He would be
the prosecution's star witness in a series of trials. This
was the final stage of Operation Gambad, the goal break
the chokehold the Mob had on Chicago. There's a little
(01:59):
story Bob told me that kind of sums up what
his life was like after he fled Chicago and It's
about of all things furniture.
Speaker 4 (02:08):
I started off I first, when I first left town.
I started off with all my own furniture and all
the rest of it.
Speaker 2 (02:14):
And all the rest of it, you know, like a
toaster and a can opener and a TV. Not just that. Initially,
Bob built a little nest for himself. After bouncing around
from east to west, he settled down in Richmond, Virginia
and started getting all domestic.
Speaker 4 (02:30):
I had met a girl who had moved in with me.
She thought maybe we'd get married, but that wasn't my idea.
But she had just moved in with me about a
week before, and I went to Chicago for a trial.
Speaker 2 (02:42):
That was the rhythm of Bob's life. Now, hide out,
keep a low profile, and then every so often, hop
on a plane back to the Chicago area, show up
in court, take the witness stand, and then poof vanish again.
All told, Bob would end up testifying in nine trials. Anyway,
(03:02):
After one of his court appearances, Bob is ready to
head home back to Richmond, where his girlfriend is waiting
for him. But first Bob needs to stop by an
FBI office just to check in.
Speaker 4 (03:14):
They had six agents standing there with machine guns and
with vests on, and they told me to put a
vest on. And they said, you can't go back home.
And I said why. They said, supposedly somebody was on
the way out there to kill me.
Speaker 2 (03:31):
Bob tries to digest all of this. I mean, things
were going pretty well for him back in Richmond, but
apparently it was time to move again.
Speaker 4 (03:40):
I said, well, I've got some stuff i'd like to get,
you know, back home, at my house. And so the
next day I flew into Richmond. A couple of agents
met me there. We went to the house and my
girlfriend I forgot her name now, wasn't home. She was
at work, and I just packed up a bunch of
(04:00):
stuff and left her a note. You know, I got
to leave. Something came up. I'm not coming back. You know,
everything here is yours.
Speaker 2 (04:08):
And that was that the end of one of Bob
Cooley's many lives. So he started over in North Carolina,
where he stayed until there was another scare and he
had to flee again. It had been twenty years since
Bob first got involved with the Mob. Ever since then,
(04:30):
he had been haunted by his relationship with its political czar,
Pat Marcy and one of its hit men, Harry Elmann.
Now they would both be prosecuted. This was the reckoning,
the moment when Bob would have to stare them down
in court, tell the world what they'd done, and explain
his own role in it all. This would happen in
(04:53):
two separate trials that took place in the nineteen nineties.
These trials would in many ways to find the success
or failure of Bob's mission, and through it all, Bob's
main challenge was to stay alive so he could finish
what he started. I'm Jay Colburn and this is Deep
(05:43):
Cover mob Land, our final episode the witness. Before Pat
(06:05):
Marcy was indicted, prosecutors invited him to their off for
a little visit. Tom Durkin was there for that meeting.
Today he's a federal judge, but at the time he
was an assistant US attorney.
Speaker 5 (06:18):
Pat Marcy came in with his lawyer. The attorney explained
what the charges would be.
Speaker 2 (06:23):
Marcy was older now, he was in his seventies and
not in the best of health, and he was in
hot water. Marcy was about to be charged on multiple counts,
including racketeering, bribery, and extortion. The prosecutors wanted to see
if Marcy might cooperate.
Speaker 5 (06:40):
And I distinctly remember Pat Marcy saying good luck to
you and standing up and walking out.
Speaker 2 (06:47):
In other words, go to hell. So Tom and the
other prosecutors had to build their case, and they had
a lot to work with. For starters, they had all
those secret recordings that Bob had made, which they could
play for the jury. These would prove that Marcy had
orchestrated bribes. Sure, sometimes Marcy spoke in code, but that's
(07:08):
where Bob would come into play. He could get on
the witness stand and offer context, almost like a translator,
decoding mob speak. The prosecutors also wanted to prove that
Marcy had arranged to fix court cases in the more
distant past before Bob had flipped, like that notorious murder
case back in the seventies involving the reputed hitman Harry Elaman.
(07:33):
The Feds wanted to prove that Marcy had schemed to
fix that case, that he was the one who'd recruited
Bob Cooley to bribe the judge. But proving this would
be much harder. Sure, Bob could testify, but there were
no secret recordings to back him up. So who could
corroborate Bob's story. The judge on the case, Frank Wilson,
was now dead. He had taken his own life, and
(07:56):
that left only one person, Catherine Fleming. If you recall
in nineteen seventy seven, the year of the Harry Elamann trial,
she was Bob's secretary and lover, but she knew little
about his shady dealings.
Speaker 6 (08:11):
I wasn't looking to figure it out because it was
none of my business.
Speaker 2 (08:15):
But Catherine was with Bob at the restaurant when he
made the payoff to Judge Wilson. She didn't see the
actual payoff or even know about it at the time,
but afterwards the judge had told her, you look like
a nice girl, stay away from him. Tom Durkin, the prosecutor,
felt that if he could persuade Catherine to testify, she
(08:38):
could be the lynchpin. Everything she witnessed indicated that Bob
was telling the truth. Catherine agreed to cooperate, but her
family was unhappy, especially her mom.
Speaker 6 (08:51):
Oh, she went nuts. She had a fit, lots of screaming.
She demanded that I'd not testify, that it had nothing
to do with me, that Bob was wrong to do this, wrong,
to involve me. She felt that he was a horrible person.
She felt that everyone was you me, and the mafia
would kill me.
Speaker 2 (09:11):
Even so, Catherine felt she had to do something.
Speaker 6 (09:15):
I thought that it's very wrong for judges to get
paid off so that hitman can continue to murder people,
and nobody wants to testify because their mothers scream at
them that you're going to get murdered. And I wanted
to do the right thing.
Speaker 2 (09:33):
Catherine's testimony would be a huge boost for Tom Dirkin
and the prosecution, especially because she had no reason to lie.
She was just a regular civilian, a bystander caught up
in a tangled scheme of corruption, and by testifying she
would in effect be taking on the mob. In short,
she bolstered Bob's credibility big time.
Speaker 5 (09:55):
It was remarkable corroboration from a witness who had no
motive to lie. I thought that was the best piece
of corroboration I've ever had in any case I ever prosecuted.
Speaker 2 (10:04):
So that was that the prosecution's case was coming together.
They had Bob, they had his secret recordings, and they
had Catherine Fleming, the stalwart secretary who would not be intimidated.
The trial of Pat Marcy kicked off on December fourteenth,
nineteen ninety two, almost exactly three years after Bob Cooley
(10:26):
fled Chicago, and on trial alongside him as co defendant,
was one of Marcy's associates, the first word Alderman Fred Roady.
In his opening statement, Marcy's defense lawyer Ed Jensen told
the jury quote, Robert Cooley is a liar who will
say or do anything to convict Pat Marcy. He's an
(10:48):
envious man who has spent his whole life lying and cheating,
and he has decided to put these talents to work
for the government. So that was the game plan. Smear
Bob before he even took the stand. Make Bob Cooley
look like the rat of all time. Eventually, Bob arrived
at the courthouse to testify, and for the first time
(11:08):
in year, he came face to face with Pat Marcy.
Speaker 4 (11:12):
I was brought into the courtroom. I was put up
in the chair. I'm sitting up there in the witness chair.
I see Pat over there and he's glaring at.
Speaker 2 (11:21):
Me, Bob says. Marcy's lawyer approached him. The two men
knew each other brushing shoulders in the city's courts.
Speaker 4 (11:30):
Jensen comes walking up to me while the jury is
being brought in and he says, how are you doing, Bob?
You know you look good? Everything okay, I get the
fuck out of here.
Speaker 2 (11:44):
Bob was a witness for the prosecution, so they got
him first for the direct questioning. Tom Dirkin, the prosecutor,
asked Bob to tell his story, the whole saga of
how he got mixed up with the mob in the
first place, how he met Pat Marcy, and what Marcy
asked him to do. Bob was calm and collected, clarifying
(12:04):
the smallest of details. As a former criminal defense lawyer,
Bob knew exactactly what he needed to do. Tom says
Bob's performance as a witness was one of the best
he ever saw.
Speaker 5 (12:15):
Every question I had was answered directly by him. The
evidence we were able to play the tapes. We put
up pictures of the main players as he was talking
about people.
Speaker 2 (12:26):
All the while Pat Marcy sat there as if none
of this had anything to do with him.
Speaker 5 (12:31):
You couldn't get any emotion out of him. He wasn't
grimacing or rolling his eyes or muttering under his breath
or anything like that. He's very stony faced.
Speaker 2 (12:39):
Bob says he also remembers Marcy's cold, hard gaze.
Speaker 4 (12:44):
Pat Marcy is staring at me. When he's staring at me,
I give him a wink. I give him a wink
and a smile, and he starts coughing. He started coughing
and wheezing, almost uncontrollably.
Speaker 2 (12:57):
As all this is happening. Tom has his back to Marcy,
so we can't see him, but he remembers hearing coughing
in the moment. Tom didn't think much of it, but
turns out it was an omen of what was to come.
A day or so later, Marcy's lawyers announced that he'd
had a heart attack.
Speaker 7 (13:16):
Tonight, Pat Marcy is in critical condition in the cardiac
care unit of West Suburban Hospital in oak Park. Despite
defense objections that the seventy nine year old Marcy should
not be tried at all due to poor health.
Speaker 2 (13:29):
The plan was to prosecute Marcy again when his health improved,
but it never did. The case against Marcy ended in
a mistrial. A short while later, Marcy died. Now you
(13:51):
might think that Bob would be devastated by this. I
mean he risked his own life and spent the last
three years on the run, all in the hopes of
nailing this guy and sending him to prison. And now this,
but that's not the way that Bob saw it. Bob,
in classic Bob fashion, credit for Marcy's death. Wait, are
you saying that you think you caused him the heart attack?
Speaker 4 (14:13):
I have no doubt in my mind. I have no
doubt in my mind. But I was gonna say, because
this man had so much hatred towards me in this system.
Speaker 2 (14:24):
The truth is, there's no real proof that Marcy had
a heart attack right there in the courtroom while Bob
was winking at him. But as Bob tells it in
his mythology, that's how it all played out. In other words,
he won, though arguably Marcy lived by his own rules
(14:45):
to the right bold age of seventy nine and checked
out just in time. I asked Tom, the prosecutor, if
he felt that Marcy had basically escaped justice.
Speaker 5 (14:57):
He didn't escape justice. He was indicted. He was held
up to the public as a person who had fixed
murder cases. He was on trial in a courtroom in
front of a jury. A lot of the secrets of
his life were exposed. So he didn't escape justice. Did
he escape going to jail, sure, but at what price
he died?
Speaker 2 (15:15):
Pat Marcy's death was a mortal blow to the First Ward.
Marcy was more than just the boss in so many ways.
He was the first Ward. He'd been there for decades,
and his connections, his know how, and the fear that
he conjured it all died with him. No one could
(15:36):
really fill his shoes, and the other possible candidates, well,
they went down with him. Fred Roady was convicted on
multiple counts of racketeering and extortion. He was sentenced to
four years in prison. As for John Diarco Junior, the
poet and state senator, his case also went to trial.
(15:56):
He was convicted of extortion and sentenced to three years
in prison. In the years since Marcie's death, the political
boundaries of Chicago's war Words have been redrawn and then
redrawn again, and the old First Ward, in both shape
and power, is no more. Bob may rightly claim credit
(16:22):
for the downfall of the First Ward, but his most
defining moment would come in another trial where he would
face off with the hit man Harry Alaman and try
to atone for his own original sin. More on that
after the break, after the trial of Pat Marcy and
(16:57):
Fred Roady, much of Bob's story became public, and one
of the biggest revelations was this Bob had bribed a
judge and helped Harry Alamann, the hit man, go freely.
That but Catherine Fleming, Bob's secretary, had provided some corroboration,
And this, among other things, raised the question would prosecutors
(17:18):
go after Harry again some twenty years later. Mind you,
doing this wouldn't be easy. Harry had a very powerful
ally on his side. And I don't mean the mob.
I'm talking about the Fifth Amendment of the US Constitution.
It said that no one could be placed in double jeopardy,
meaning you can't be prosecuted for the same crime twice.
(17:39):
But turns out state prosecutors came up with a clever workaround.
They argued that because the original trial appeared to have
been fixed, well, then Harry had never really been in
jeopardy in the first place. Hattie. This question was actually
appealed all the way up to the US Supreme Court.
In the end, the decision was Harry could be retried.
Speaker 8 (18:02):
Now.
Speaker 2 (18:02):
To give you a quick refresher. The first trial of
Harry Alamann occurred back in nineteen seventy six. There were
two eyewitnesses, both of whom identified Harry as the killer.
The public and Chicago media were shocked by the not
guilty verdict, but no one was more deeply impacted than
the family of the victim, Billy Logan. Billy's niece, Johanna
(18:26):
Santanello says her relatives were haunted for years by what
had happened.
Speaker 9 (18:31):
They have nothing but this memory of how they last
seen their family member laying on a street full of
bull of the hole's moaning.
Speaker 2 (18:44):
They wondered how exactly that trial had ended in an acquittal,
and they held on to the hope that somehow justice
still might be served. And then finally, in nineteen ninety seven,
two decades later, Harry was put back on trial, thanks
in part to Bob Cooley and the fact that he
would testify. But the whole thing left Johannah feeling worried.
Speaker 9 (19:06):
Because I just felt, what if he walks again, you know,
how would my family handle that or could they handle
any more of this?
Speaker 2 (19:20):
In many ways, this retrial was a culmination, a moment
of truth not just for the Logan family or even
for Operation Gambat, but for everyone in Chicago who'd witnessed
untold decades of judicial corruption. The credibility of the judicial
system itself seemed to be on the line, because in
the end, laws and judges and courthouses don't mean a
(19:44):
damn thing if no one has faith in them. As
the trial got underway, the prosecution called its witnesses to
the stand, many of the same people who testified twenty
years earlier. It was a bit like the reunion of
an old TV show, with the same actors and a
(20:04):
few new twists. There was the neighbor who said he'd
witnessed the murder, the accomplice who said he'd helped Harry
plan the whole thing. And there were new witnesses too,
including Bob Cooley. Bob says he showed up with his
own security detail.
Speaker 4 (20:19):
Well, I guess it was like the mayor or the
rising coming in. They were so worried about my security
because of obviously this was going to be a case
that would be making history.
Speaker 10 (20:32):
It's a very big deal.
Speaker 2 (20:34):
Investigative reporter Carol Marine covered the trial. She also remembers
all the fanfare surrounding Bob.
Speaker 10 (20:41):
They're surrounded by agents. They're in bulletproof vests. They're guarding you.
Speaker 3 (20:47):
They've got automatic weapons everywhere.
Speaker 10 (20:51):
Yes, you are the center of the universe.
Speaker 2 (20:57):
When he finally took the stand, Bob told the courtroom
how in the past he'd been a fixer for Pat
Marcy and the first ward he was in effect a
tool of the outfit who'd been asked to protect when
of their most valuable assets, Harry the hook Alaman. Bob
explained how in the original trial he'd bribed the judge,
(21:17):
Frank Wilson, and how later after the not guilty verdict
came out, the judge had told him, you destroyed me.
Carol was there in the courtroom for this moment.
Speaker 3 (21:30):
You know, Bob Cooley does not demonstrate much emotion at all.
He's got a pretty flat affect. But there was a
point in his testimony talking about really almost forcing Frank
Wilson to take the money in a men's bathroom. I mean,
he choked with emotion and had to kind of swallow
(21:52):
hard and.
Speaker 10 (21:53):
Keep talking.
Speaker 3 (21:55):
Because he knew that he was one of the instruments
of Frank Wilson's demise. He couldn't have been other. Yes,
the outfit ruined Frank Wilson. Yes, Frank Wilson ruined Frank Wilson,
But ultimately all of the players in the surround sound
(22:17):
of that were responsible for the death of Frank Wilson.
Speaker 2 (22:27):
Afterwards, Harry's lawyer had a chance to cross examine Bob.
His strategy from the start was to discredit him, to
dredge up Bob's checkered past. He asked Bob if during
his days as a cop he'd ever been paid off. Yes,
said Bob, He'd taken so called street money that typically
meant tips or payoffs from businesses, you know, like bars
(22:50):
that want to cozy up with the cops. The defense
lawyer kept hammering away at Bob, portraying him as a
shifty and shadowy character. In response, Bob was remarkably candid.
He didn't make elaborate arguments or justifications. He just kind
of took it on the chin. At one point, he said, quote,
(23:10):
I'm not making any excuses for what I did. I
did what I did, but it was an easy way
to get to the top during that time, and I
took the easy route.
Speaker 4 (23:19):
This guy is trying to make me out to be
somebody who's you know, who's a crooked cough passing out bribes.
Speaker 11 (23:25):
Because I guess what he's trying to do is the
classic I'm going to turnish your reputation and credibility. But
the whole purpose of you appearing today as as a
guy who fixes cases in places bribes.
Speaker 4 (23:35):
It's given me credibility in that sense.
Speaker 2 (23:38):
The whole process was tricky for Bob. He wanted to
be seen as the guy who'd cleaned up Chicago, but
in order to do that, he had to admit publicly
to all the most questionable and unsavory things that he'd
ever done. The danger was that these admissions would define
who Bob really was because everyone was trying to make
(24:01):
up their minds about Bob. In his closing statement, the
prosecutor told the jury quote, I'm telling you you have
to like Bob Cooley. You don't have to like him,
but you know what. Bob Cooley faced what he was.
As the jury finished its deliberations, onlookers packed into the
(24:23):
gallery to hear the verdict. Johanna Santanello was there with
the other members of a Logan family, hoping that maybe
finally there'd be justice for Billy. The jurors came into
the courtroom and then the verdict was announced for the.
Speaker 9 (24:40):
Murder of William Logan guilty, and it was like, oh
my god, it's happening. All these years they waited my
aunt and my uncle and my mom to hear that guilty,
and it was finally like a burden was lifted off
(25:05):
of them. Of course, their brother could never be replaced,
no matter, you know, but to see him actually have
to pay for what he did meant the world to them.
Speaker 2 (25:20):
So, according to the Chicago Tribune, when the verdict was announced,
Harry Alamann didn't flinch. He simply blinked his eyes and
stared straight ahead. Harry was eventually sentenced to one hundred
(25:44):
to three hundred years in prison. He died behind bars
after the trial. As reporters clamored for quotes and comments,
one prosecutor proclaimed, quote, this will close the books on
an ugly era in Cook County. It's a great day
(26:04):
for American justice. The one person who was conspicuously absent
at that moment was Bob Cooley. After testifying, Bob flew
off to another undisclosed destination, vanishing once again even so
(26:28):
Bob's presence loomed large in the courtroom that day. After all,
he was the man who'd both started and finished this saga,
the fixer who bribed the judge in the first trial
and then exposed his own trickery at the second trial.
He was a rat or a hero, depending on who
you asked. But one thing was clear. Bob's work in
(26:50):
Chicago is now done. He hadn't expected to survive this process,
but he had. In fact, he was just fifty five
years old. So now what what kind of life could
he really expect? And had it all been worth it?
Speaker 12 (27:24):
Caam driving down a desert highway here? And so you
got to make him turn left, turn.
Speaker 4 (27:33):
In a mile. Well is.
Speaker 2 (27:41):
Dusty and bleak out here. After almost a year of
talking to Bob on the phone, I went to see
him in the obscure little corner of the world where
he now lives.
Speaker 8 (27:55):
You got to make a left up here. Oh, oh, yeah, somewhere.
I think I'm about to miss out here. It is here,
It is okay, Wow, it's.
Speaker 12 (28:06):
Easy to miss.
Speaker 2 (28:08):
Bob lives in a modest house at the edge of
the desert.
Speaker 4 (28:12):
Here.
Speaker 2 (28:12):
He has a small bedroom which he calls his cubby hole.
His bedroom floor is stacked with cylinders of pringles and
jugs of V eight vegetable juice that Bob buys in
bulk to save money. The place looks like what it is,
a hideout.
Speaker 11 (28:27):
Hi are you Rosie?
Speaker 2 (28:31):
Bob has a roommate, a woman named Rosie. When I visited,
she was wearing a house dress with brightly colored, psychedelic
looking flowers. She's actually the one who owns this house.
Bob told me that he's lived with her on and
off for roughly a decade.
Speaker 4 (28:48):
She said, I'm pretty much of a recluse. She said,
I keep to myself or whatever. And I said, you know, well,
I think i'd like to move in. She had no
idea who I was.
Speaker 2 (28:57):
Rosie told me that she knew the broad strokes of
Bob's life, but never asked about the details.
Speaker 13 (29:04):
We don't talk.
Speaker 2 (29:06):
Wait, how come you never talk your roommate.
Speaker 13 (29:10):
He lives his life. I live my life minus with
the dogs back there, and his is in here, so
that's it. He comes in the kitchen. I'm not in
the kitchen. He does all the cooking. I don't do
any cooking.
Speaker 11 (29:25):
But aren't you curious?
Speaker 2 (29:26):
Like he used to work for the MOB as a lawyer.
Speaker 12 (29:29):
Does that make you want to know more?
Speaker 10 (29:30):
No?
Speaker 13 (29:31):
No, no, I don't.
Speaker 10 (29:35):
That's me.
Speaker 13 (29:37):
No, I don't need to know.
Speaker 2 (29:40):
So in some ways, Rosie is the perfect housemate for Bob.
She doesn't pry, though I should point out they did,
in fact talk. They argued more or less constantly during
the time that I was there, not small things like
whether the living room needed dusting or how the pillows
were situated on the couch. Rosie told me that Bob
had messed them up.
Speaker 4 (30:01):
I'm kind of embarrassed, though I hope he doesn't take
a picture of that.
Speaker 13 (30:05):
Kidding, you're embarrassed, Give me a break.
Speaker 12 (30:11):
You guys are a regular odd couple. I gotta tell.
Speaker 13 (30:13):
You we are we if we would be married, I
polly killed him by now.
Speaker 4 (30:20):
Just to get the insurance right.
Speaker 10 (30:22):
Absolutely.
Speaker 2 (30:24):
Eventually, I suggested that Bob and I get out of
the house get some space. So we hopped in my
rental car, and as we drove we chatted. He told
me how lonely he was in the years after he
first left Chicago.
Speaker 4 (30:38):
As I'm driving around, I'm so jealous of people. Look,
I say, somebody with somebody in the car with them,
and I'm jealous. I mean, it's really hard to explain this.
Speaker 14 (30:47):
I'm curious, like, here you are, You're in this town,
you're at this roommate live with you for eight years
and knows nothing about you've got. You said, you've got
no friends in this town. I mean, are you good
with that?
Speaker 2 (30:58):
Are you at peace with that?
Speaker 4 (30:59):
Or are you at the moment at the moment, yes,
you know no, As I said, what are you gonna?
What am I gonna do? I can't feel sorry for myself.
It's such a decision I made, and I suspected it
would be bad, never as bad as I'd got in
terms of, you know, fighting off the loneliness for a
(31:20):
long period of time.
Speaker 2 (31:22):
As we continued driving, Bob pointed out a few of
the local landmarks, restaurants and the like that he told
me he was so strapped for cash that he hadn't
really dined out in years. Bob also showed me the
office of his lawyer, who recently helped him file for bankruptcy.
Bob told me that he'd been living off credit cards
for a while, but then the monthly payments got so
(31:44):
high that they ate up what little money he made
from Social Security, so declaring bankruptcy, it had been kind
of a relief over the past twenty five years. It
hasn't always been like this for Bob. He says that
when he initially left Chicago, he had some money in savings,
(32:05):
but Bob, ever the gambler, had made some risky bets
on the stock market and lost almost all of it.
Bob also co wrote a memoir with a journalist, Hillel Levin.
He made some money off the book, but that was
back in two thousand and four, and in the years
since then, he's been kind of scraping by. It's ironic really.
(32:29):
As a kid, Bob loathed the feeling of being poor.
Remember he hated that his mother had to comb the
shelves looking for dented cans so she could ask for
a discount. This, as much as anything, fueled his ambitions
to become wealthy, to become no tie gold chain Bob
a guy who walked around town with thousands of dollars
(32:51):
in his pockets and now here he was all these
years later, clipping coupons and buying V eight and pringles
in bulk to make his money. Last in the Hollywoo version,
of this story, the Bob character would likely have ended
(33:13):
up on the beach somewhere, maybe down in the Caymans,
but that's obviously not how it panned out for him.
And this got me thinking, what was the ending that
Bob deserved, you know, given everything that he'd done. I mean,
it was complicated. Bob was the guy who induced his
friend into taking a bribe that ruined him, a guy
(33:36):
who helped a murderer walk free, a guy who prevented
a female cop who'd been beaten from getting justice. But
this was also the guy who tried to right these wrongs.
He'd shown tremendous courage. Bob made a stand against the
mob and expose systematic corruption, and the impact he had
in the city of Chicago, it's indisputable. Here's Carol Marine,
(34:00):
the investigative journalist.
Speaker 3 (34:02):
Bob was one of the most consequential witnesses that ever
took the stand in a federal organized crime trial or
probably almost any trial. He did this city and this
state a great service. He risked his life. He did
something that no one else had done. He penetrated the
(34:26):
first Ward and he took down its power brokers. It
was tremendously important in fighting public corruption.
Speaker 2 (34:36):
Of course, Chicago still has its challenges. In twenty nineteen,
the city's longest serving aldermen, a guy named Ed Burke,
was indicted on fourteen counts of racketeering, extortion, and bribery.
Burke went down because another city alderman betrayed him. That
guy wore a wire for two years and made a
(34:58):
series of secret recordings. It was a long con. Seemed
like he took a page right out of Bob Cooley's playbook.
Operation Gambat may now seem like ancient history, something that
happened way back in the eighties, but the ripple effects
are still being felt to this day. There's this concept
(35:20):
in the law known as camouflaging bias. The idea is
a judge takes a bribe in one case and then
to avoid suspicion, punishes the hell out of other defendants
so it looks like the judge is tough on crime.
Then years later the defendant cries foul, says, hey, that
wasn't fair. I got hit with this huge sentence because
(35:41):
this corrupt judge was covering his tracks. And that's what's
happening in Chicago right now. Prisoners arguing that they too
were victims of the corruption that Bob exposed, And so
the story goes on. Some members of Bob's family really
(36:02):
appreciate what he did for the city of Chicago. His
brother Joe, who was an assistant US attorney, told me
that he was proud of Bob's legacy, and his brother
Dennis told me he gradually came to respect what Bob
had done. But it's been trickier with some of Bob's
other siblings.
Speaker 4 (36:20):
I mean, and I have a sister and another brother
who want nothing to do with me. They want absolutely
nothing to do with me. Why do you think that
is because they believe what they saw that I'm some
kind of a rat. I mean, why else would it be.
Speaker 2 (36:35):
I spoke with both of the siblings Bob's referring to here,
Tim and Diane. Both of them conveyed to me in
so many words that they cared about Bob, but they'd
never really been close with him. That even as a kid,
Bob had been unscrupulous, hot headed, and full of himself.
I talked about this at length with Tim Cooley. If
(36:57):
you recall, Tim is the yoga instructor who lives in Vermont.
Speaker 15 (37:01):
I don't know.
Speaker 10 (37:02):
You know, why is Bob Bob?
Speaker 15 (37:03):
You know I I've been thinking about it and and
this may sound weird, but I don't know if Bob
has ever felt loved. I've never known a loving relationship
that he's been in. Actually, you know, he's had a
lot of sex, I'm sure, but I don't think he's
(37:25):
ever been in love. He's never had a relationship that
I've ever been aware of, And so it's like he's
looking for he's looking to fill that lack in some
other ways.
Speaker 2 (37:40):
Tim offered me a take on his brother that was
neither rat nor hero, but something else altogether.
Speaker 10 (37:48):
I'm afraid that.
Speaker 15 (37:50):
That what matters most of all is just that he's known,
that he's known, and the goodness is almost irrelevant. I'm
sorry to say. The most important thing is that, look,
I am a big man. Look I am somebody. I
(38:14):
can do really horrible things, I can do good things.
I'm somebody.
Speaker 2 (38:20):
When I relayed all of this back to Bob, word
for word, to my great surprise, Bob shrugged his shoulders
and said he's right in a sense. In the year
that I spent talking with Bob, he was always upbeat
and quick to laugh. Part of this is just Bob's nature,
(38:42):
but I think he was also kind of selling me
on his story, as if to say, look at me,
I live quite a life, didn't I? And he had.
But when I visited Bob in person and saw his
cubby hole and the roommate who didn't really know him
or cared to know him, I got a different feeling entirely.
(39:03):
Bob's bravada was gone, and in its place was an
air of defeat and almost disbelief, as if he couldn't
quite fathom that this is how things had turned out.
I asked Bob if there was any part of him
that regretted what he'd done, if he could go back
in time, would he have done it differently? Not flipped
(39:24):
at all?
Speaker 4 (39:26):
Absolutely, I mean absolutely. The day I put on that
wire it was all over. I knew it was all over.
I knew that, you know, my life could never be,
But I never dreamed it would be as bad as God.
I'm no better rop than some of those beggars out
there in the street, and I'd better not even think
(39:50):
about it, because again, it is the way it is.
So I mean to say, I wish I could have
changed that are you kidding me.
Speaker 12 (39:57):
I mean, I'm trying to understand how you think about
your own life. If the defining thing in your life
is the thing you wish you hadn't done.
Speaker 4 (40:05):
You've seen my life now. Think about that. You've seen
my life now, and you can't understand how I wished
I hadn't done that. That makes no sense.
Speaker 12 (40:19):
Well, I understand it. It's not that I don't understand it.
Speaker 4 (40:23):
I just.
Speaker 12 (40:25):
Trying to wrap my head around it, that's all.
Speaker 4 (40:27):
But you know, again, I don't know. I'm just saying that.
There's no question in my mind. I'd be an idiot
to say, gee, I'm glad that I, you know, destroyed myself,
and that's what I wound up doing. I destroyed. Bob
Cooley is no longer. This is not Bob Cooley name
wise or even otherwise. What do you mean they left?
(40:49):
Bob Cooley was that person back there in Chicago that
everybody came to when they had trouble and was able
to help all kinds of people and be able to
do whatever he damned pleased, never worried about getting arrested
or getting parking tickets or anything whatever I wanted.
Speaker 12 (41:04):
What is Bob Cooley.
Speaker 4 (41:05):
Now just just to you know, somebody waiting to die.
That pretty much sums it all up right now at
this stage. I mean, they you kidding me? What is it?
He's nobody, he's nothing.
Speaker 2 (41:24):
Hearing him talk like this, I had to wonder once
again why Bob had flipped in the first place. What
had he been hoping for. There were so many different theories,
and Bob himself kind of waffled on this question, offering
different explanations on different days. It was to clean up
the city, it was to heed the advice of his
(41:46):
dying father. He was to stand up to Pat Marcy,
who was a bully. And it's true Bob did not
like being pushed around. But my feeling about all of
these was yeah, maybe, but they seemed like partial explanations
at best. The theory I heard the most was that
(42:08):
Bob owed to the mob. That's what was in all
the papers at the time. But I don't really buy it.
I mean, think about the timeline. Bob flipped back in
nineteen eighty six, he fled town in nineteen eighty nine.
So put yourself in Bob's shoes if you were truly
worried about owing money to the mob, and you were
(42:29):
spooped that some goons were going to break your legs
were worse, Why would you flip and then stick around
town for the next three and a half years. You wouldn't.
It's true Bob was a gambler, and I think that
this does in fact explain what he did. I kept
thinking back to what Bob told me on the very
(42:51):
first day that we talked, that he'd been walking down
the street to get a Deli sandwich, he'd seen the
Prosecutor's office and just walked in on an impulse. And
now I could see it. Here's Bob the gambler, because
walking into that office was, in some ways the biggest
gamble of all. He was wagering his life. He was
(43:14):
betting that he could almost magically save himself and perhaps
the city of Chicago while he was at it. Not
a sensible bet, a real long shot, you might say,
which is probably exactly why he did it. One day,
(43:45):
toward the end of my visit with Bob, we had
lunch together at the little place where I was staying.
I ordered her some pizza, which we didn't finish, and
I was about to throw the leftover slices out when
Bob stopped me, no save those. He told me he
wanted to feed the wildlife.
Speaker 12 (44:03):
Why do you like to do it?
Speaker 4 (44:04):
Because I've been doing it all my life pretty much.
I like to feed the animals.
Speaker 10 (44:09):
Why.
Speaker 4 (44:11):
I'll be rewarded down the road for it.
Speaker 12 (44:14):
It's always something for something.
Speaker 4 (44:16):
I like you. I like animals. You know, I feel
bad when I see him out there. You know they
might be going hungry. It's always been my nature. I
just do it.
Speaker 2 (44:27):
We took the scraps of pizza and drove over to
one of Bob's favorite spots. It was at the edge
of a parking lot next to a strip mall. He
came here often. This is kind of a random spot.
Speaker 5 (44:39):
Why do you pick this spot?
Speaker 4 (44:40):
We're like, we're at a over You'll see them all
over here over on the other side. There, they've got
a fast food restaurant, two fast food restaurants, and that's
where the birds seem to migrate.
Speaker 2 (44:58):
I stood there and watched as the birds flocked around him,
swirling and chirping. For a moment, he seemed genuinely content.
The whole scene reminded me of how back when he
was still in Chicago, wearing a wire. He used to
feed the baby raccoons with no ulterior motives, just a
(45:19):
pure and simple act, a real rarity, because nothing in
Bob's life was ever simple.
Speaker 12 (45:38):
Your herds are up there at the corner, looks like yeah.
Speaker 4 (45:40):
No, they for some reason, they always fly away and
then they come back. But you'll get them cross the
way over here and they'll come back and get it.
The braver ones get fed the most. There's some of
(46:05):
them coming up above.
Speaker 2 (46:50):
Deep Cover is produced by Jacob Smith and Amy Gaines
and edited by Karen Chakerji. Our senior editor is Jen Guera.
Original music and the deep Cover theme was composed by
Luis Garra, with performances by Luise Audrian Terrasas, Alan Fajardo,
Mi Longoria, and Jimmy Messer. Flawn Williams is our engineer.
(47:13):
Our art this season was drawn by Cheryl Cook and
designed by Sean Carney. Mia Lobel is our executive producer.
Special thanks to Heather Fain, John Schnarz, Carly Migliori, Maya Caning,
Christina Sullivan, Eric Sandler, Mary Beth Smith, Brant Haynes, Maggie Taylor,
Nicole Morano, Megan Larson, Morgan Ratner, Royston Deserve, Lucy Sullivan,
(47:37):
Edith Russello, Riley Sullivan, Jen Sanchez, Jason Gambrell, Martin Gonzalez,
and Jacob Weisberg. Additional special thanks to Jill Gillette, Travis Dunlap,
Maggie de Poy, Bill Hogan, David Grossman, Mike Shephard, Jim Wagner,
Denny Cherrillo, Lisa Chase Patterson, and Michael Deutsch. Also Christian McNally,
(48:01):
Isabel Vasquez, Jesse de Bartolomeo, Jane Miliotis, Sarah Kraditch, and
the National Archives at CHU Chicago. I'm Jake Halbert. If
(48:53):
you like this season of deep Cover, then you should
really check out our first season, The Drug Wars, which
tells the story of an FBI agent who goes under
cover with a biker gang and uncovers a series of
clues that leads to a war, I mean, a full
scale invasion. Also check out Pushkin's other true crime podcasts,
(49:14):
Lost Hills and Bad Women. These shows and more are
available ad free for Pushkin Plus subscribers. To find more
Pushkin podcasts, listen on the iHeartRadio app, Apple Podcasts, or
wherever you listen to podcasts,
Pushkin previously on Deep Cover.
Speaker 2 (00:45):
Bob Cooley fled Chicago in November of nineteen eighty nine.
Bob's life as he knew it was over. He had
rejected the witness protection program and instead opted to improvise.
He took on a new identity and planned to hide
out Meanwhile, back in Chicago, Bob's efforts resulted in charges
(01:05):
against at least two dozen men, lawyers, judges, cops, and politicians.
Chief among them was Pat Marcy, who effectively ran the
first ward, the Mob's political stronghold.
Speaker 3 (01:17):
So this is like a not just a cascade, it's
an earthquake on Chicago politics. This is a staggering revelation
involving a lawyer. Virtually no one outside of a circle
of real insiders knew at all.
Speaker 2 (01:35):
Bob's days as a covert operative may have been over,
but he still had work to do. He would be
the prosecution's star witness in a series of trials. This
was the final stage of Operation Gambad, the goal break
the chokehold the Mob had on Chicago. There's a little
(01:59):
story Bob told me that kind of sums up what
his life was like after he fled Chicago and It's
about of all things furniture.
Speaker 4 (02:08):
I started off I first, when I first left town.
I started off with all my own furniture and all
the rest of it.
Speaker 2 (02:14):
And all the rest of it, you know, like a
toaster and a can opener and a TV. Not just that. Initially,
Bob built a little nest for himself. After bouncing around
from east to west, he settled down in Richmond, Virginia
and started getting all domestic.
Speaker 4 (02:30):
I had met a girl who had moved in with me.
She thought maybe we'd get married, but that wasn't my idea.
But she had just moved in with me about a
week before, and I went to Chicago for a trial.
Speaker 2 (02:42):
That was the rhythm of Bob's life. Now, hide out,
keep a low profile, and then every so often, hop
on a plane back to the Chicago area, show up
in court, take the witness stand, and then poof vanish again.
All told, Bob would end up testifying in nine trials. Anyway,
(03:02):
After one of his court appearances, Bob is ready to
head home back to Richmond, where his girlfriend is waiting
for him. But first Bob needs to stop by an
FBI office just to check in.
Speaker 4 (03:14):
They had six agents standing there with machine guns and
with vests on, and they told me to put a
vest on. And they said, you can't go back home.
And I said why. They said, supposedly somebody was on
the way out there to kill me.
Speaker 2 (03:31):
Bob tries to digest all of this. I mean, things
were going pretty well for him back in Richmond, but
apparently it was time to move again.
Speaker 4 (03:40):
I said, well, I've got some stuff i'd like to get,
you know, back home, at my house. And so the
next day I flew into Richmond. A couple of agents
met me there. We went to the house and my
girlfriend I forgot her name now, wasn't home. She was
at work, and I just packed up a bunch of
(04:00):
stuff and left her a note. You know, I got
to leave. Something came up. I'm not coming back. You know,
everything here is yours.
Speaker 2 (04:08):
And that was that the end of one of Bob
Cooley's many lives. So he started over in North Carolina,
where he stayed until there was another scare and he
had to flee again. It had been twenty years since
Bob first got involved with the Mob. Ever since then,
(04:30):
he had been haunted by his relationship with its political czar,
Pat Marcy and one of its hit men, Harry Elmann.
Now they would both be prosecuted. This was the reckoning,
the moment when Bob would have to stare them down
in court, tell the world what they'd done, and explain
his own role in it all. This would happen in
(04:53):
two separate trials that took place in the nineteen nineties.
These trials would in many ways to find the success
or failure of Bob's mission, and through it all, Bob's
main challenge was to stay alive so he could finish
what he started. I'm Jay Colburn and this is Deep
(05:43):
Cover mob Land, our final episode the witness. Before Pat
(06:05):
Marcy was indicted, prosecutors invited him to their off for
a little visit. Tom Durkin was there for that meeting.
Today he's a federal judge, but at the time he
was an assistant US attorney.
Speaker 5 (06:18):
Pat Marcy came in with his lawyer. The attorney explained
what the charges would be.
Speaker 2 (06:23):
Marcy was older now, he was in his seventies and
not in the best of health, and he was in
hot water. Marcy was about to be charged on multiple counts,
including racketeering, bribery, and extortion. The prosecutors wanted to see
if Marcy might cooperate.
Speaker 5 (06:40):
And I distinctly remember Pat Marcy saying good luck to
you and standing up and walking out.
Speaker 2 (06:47):
In other words, go to hell. So Tom and the
other prosecutors had to build their case, and they had
a lot to work with. For starters, they had all
those secret recordings that Bob had made, which they could
play for the jury. These would prove that Marcy had
orchestrated bribes. Sure, sometimes Marcy spoke in code, but that's
(07:08):
where Bob would come into play. He could get on
the witness stand and offer context, almost like a translator,
decoding mob speak. The prosecutors also wanted to prove that
Marcy had arranged to fix court cases in the more
distant past before Bob had flipped, like that notorious murder
case back in the seventies involving the reputed hitman Harry Elaman.
(07:33):
The Feds wanted to prove that Marcy had schemed to
fix that case, that he was the one who'd recruited
Bob Cooley to bribe the judge. But proving this would
be much harder. Sure, Bob could testify, but there were
no secret recordings to back him up. So who could
corroborate Bob's story. The judge on the case, Frank Wilson,
was now dead. He had taken his own life, and
(07:56):
that left only one person, Catherine Fleming. If you recall
in nineteen seventy seven, the year of the Harry Elamann trial,
she was Bob's secretary and lover, but she knew little
about his shady dealings.
Speaker 6 (08:11):
I wasn't looking to figure it out because it was
none of my business.
Speaker 2 (08:15):
But Catherine was with Bob at the restaurant when he
made the payoff to Judge Wilson. She didn't see the
actual payoff or even know about it at the time,
but afterwards the judge had told her, you look like
a nice girl, stay away from him. Tom Durkin, the prosecutor,
felt that if he could persuade Catherine to testify, she
(08:38):
could be the lynchpin. Everything she witnessed indicated that Bob
was telling the truth. Catherine agreed to cooperate, but her
family was unhappy, especially her mom.
Speaker 6 (08:51):
Oh, she went nuts. She had a fit, lots of screaming.
She demanded that I'd not testify, that it had nothing
to do with me, that Bob was wrong to do this, wrong,
to involve me. She felt that he was a horrible person.
She felt that everyone was you me, and the mafia
would kill me.
Speaker 2 (09:11):
Even so, Catherine felt she had to do something.
Speaker 6 (09:15):
I thought that it's very wrong for judges to get
paid off so that hitman can continue to murder people,
and nobody wants to testify because their mothers scream at
them that you're going to get murdered. And I wanted
to do the right thing.
Speaker 2 (09:33):
Catherine's testimony would be a huge boost for Tom Dirkin
and the prosecution, especially because she had no reason to lie.
She was just a regular civilian, a bystander caught up
in a tangled scheme of corruption, and by testifying she
would in effect be taking on the mob. In short,
she bolstered Bob's credibility big time.
Speaker 5 (09:55):
It was remarkable corroboration from a witness who had no
motive to lie. I thought that was the best piece
of corroboration I've ever had in any case I ever prosecuted.
Speaker 2 (10:04):
So that was that the prosecution's case was coming together.
They had Bob, they had his secret recordings, and they
had Catherine Fleming, the stalwart secretary who would not be intimidated.
The trial of Pat Marcy kicked off on December fourteenth,
nineteen ninety two, almost exactly three years after Bob Cooley
(10:26):
fled Chicago, and on trial alongside him as co defendant,
was one of Marcy's associates, the first word Alderman Fred Roady.
In his opening statement, Marcy's defense lawyer Ed Jensen told
the jury quote, Robert Cooley is a liar who will
say or do anything to convict Pat Marcy. He's an
(10:48):
envious man who has spent his whole life lying and cheating,
and he has decided to put these talents to work
for the government. So that was the game plan. Smear
Bob before he even took the stand. Make Bob Cooley
look like the rat of all time. Eventually, Bob arrived
at the courthouse to testify, and for the first time
(11:08):
in year, he came face to face with Pat Marcy.
Speaker 4 (11:12):
I was brought into the courtroom. I was put up
in the chair. I'm sitting up there in the witness chair.
I see Pat over there and he's glaring at.
Speaker 2 (11:21):
Me, Bob says. Marcy's lawyer approached him. The two men
knew each other brushing shoulders in the city's courts.
Speaker 4 (11:30):
Jensen comes walking up to me while the jury is
being brought in and he says, how are you doing, Bob?
You know you look good? Everything okay, I get the
fuck out of here.
Speaker 2 (11:44):
Bob was a witness for the prosecution, so they got
him first for the direct questioning. Tom Dirkin, the prosecutor,
asked Bob to tell his story, the whole saga of
how he got mixed up with the mob in the
first place, how he met Pat Marcy, and what Marcy
asked him to do. Bob was calm and collected, clarifying
(12:04):
the smallest of details. As a former criminal defense lawyer,
Bob knew exactactly what he needed to do. Tom says
Bob's performance as a witness was one of the best
he ever saw.
Speaker 5 (12:15):
Every question I had was answered directly by him. The
evidence we were able to play the tapes. We put
up pictures of the main players as he was talking
about people.
Speaker 2 (12:26):
All the while Pat Marcy sat there as if none
of this had anything to do with him.
Speaker 5 (12:31):
You couldn't get any emotion out of him. He wasn't
grimacing or rolling his eyes or muttering under his breath
or anything like that. He's very stony faced.
Speaker 2 (12:39):
Bob says he also remembers Marcy's cold, hard gaze.
Speaker 4 (12:44):
Pat Marcy is staring at me. When he's staring at me,
I give him a wink. I give him a wink
and a smile, and he starts coughing. He started coughing
and wheezing, almost uncontrollably.
Speaker 2 (12:57):
As all this is happening. Tom has his back to Marcy,
so we can't see him, but he remembers hearing coughing
in the moment. Tom didn't think much of it, but
turns out it was an omen of what was to come.
A day or so later, Marcy's lawyers announced that he'd
had a heart attack.
Speaker 7 (13:16):
Tonight, Pat Marcy is in critical condition in the cardiac
care unit of West Suburban Hospital in oak Park. Despite
defense objections that the seventy nine year old Marcy should
not be tried at all due to poor health.
Speaker 2 (13:29):
The plan was to prosecute Marcy again when his health improved,
but it never did. The case against Marcy ended in
a mistrial. A short while later, Marcy died. Now you
(13:51):
might think that Bob would be devastated by this. I
mean he risked his own life and spent the last
three years on the run, all in the hopes of
nailing this guy and sending him to prison. And now this,
but that's not the way that Bob saw it. Bob,
in classic Bob fashion, credit for Marcy's death. Wait, are
you saying that you think you caused him the heart attack?
Speaker 4 (14:13):
I have no doubt in my mind. I have no
doubt in my mind. But I was gonna say, because
this man had so much hatred towards me in this system.
Speaker 2 (14:24):
The truth is, there's no real proof that Marcy had
a heart attack right there in the courtroom while Bob
was winking at him. But as Bob tells it in
his mythology, that's how it all played out. In other words,
he won, though arguably Marcy lived by his own rules
(14:45):
to the right bold age of seventy nine and checked
out just in time. I asked Tom, the prosecutor, if
he felt that Marcy had basically escaped justice.
Speaker 5 (14:57):
He didn't escape justice. He was indicted. He was held
up to the public as a person who had fixed
murder cases. He was on trial in a courtroom in
front of a jury. A lot of the secrets of
his life were exposed. So he didn't escape justice. Did
he escape going to jail, sure, but at what price
he died?
Speaker 2 (15:15):
Pat Marcy's death was a mortal blow to the First Ward.
Marcy was more than just the boss in so many ways.
He was the first Ward. He'd been there for decades,
and his connections, his know how, and the fear that
he conjured it all died with him. No one could
(15:36):
really fill his shoes, and the other possible candidates, well,
they went down with him. Fred Roady was convicted on
multiple counts of racketeering and extortion. He was sentenced to
four years in prison. As for John Diarco Junior, the
poet and state senator, his case also went to trial.
(15:56):
He was convicted of extortion and sentenced to three years
in prison. In the years since Marcie's death, the political
boundaries of Chicago's war Words have been redrawn and then
redrawn again, and the old First Ward, in both shape
and power, is no more. Bob may rightly claim credit
(16:22):
for the downfall of the First Ward, but his most
defining moment would come in another trial where he would
face off with the hit man Harry Alaman and try
to atone for his own original sin. More on that
after the break, after the trial of Pat Marcy and
(16:57):
Fred Roady, much of Bob's story became public, and one
of the biggest revelations was this Bob had bribed a
judge and helped Harry Alamann, the hit man, go freely.
That but Catherine Fleming, Bob's secretary, had provided some corroboration,
And this, among other things, raised the question would prosecutors
(17:18):
go after Harry again some twenty years later. Mind you,
doing this wouldn't be easy. Harry had a very powerful
ally on his side. And I don't mean the mob.
I'm talking about the Fifth Amendment of the US Constitution.
It said that no one could be placed in double jeopardy,
meaning you can't be prosecuted for the same crime twice.
(17:39):
But turns out state prosecutors came up with a clever workaround.
They argued that because the original trial appeared to have
been fixed, well, then Harry had never really been in
jeopardy in the first place. Hattie. This question was actually
appealed all the way up to the US Supreme Court.
In the end, the decision was Harry could be retried.
Speaker 8 (18:02):
Now.
Speaker 2 (18:02):
To give you a quick refresher. The first trial of
Harry Alamann occurred back in nineteen seventy six. There were
two eyewitnesses, both of whom identified Harry as the killer.
The public and Chicago media were shocked by the not
guilty verdict, but no one was more deeply impacted than
the family of the victim, Billy Logan. Billy's niece, Johanna
(18:26):
Santanello says her relatives were haunted for years by what
had happened.
Speaker 9 (18:31):
They have nothing but this memory of how they last
seen their family member laying on a street full of
bull of the hole's moaning.
Speaker 2 (18:44):
They wondered how exactly that trial had ended in an acquittal,
and they held on to the hope that somehow justice
still might be served. And then finally, in nineteen ninety seven,
two decades later, Harry was put back on trial, thanks
in part to Bob Cooley and the fact that he
would testify. But the whole thing left Johannah feeling worried.
Speaker 9 (19:06):
Because I just felt, what if he walks again, you know,
how would my family handle that or could they handle
any more of this?
Speaker 2 (19:20):
In many ways, this retrial was a culmination, a moment
of truth not just for the Logan family or even
for Operation Gambat, but for everyone in Chicago who'd witnessed
untold decades of judicial corruption. The credibility of the judicial
system itself seemed to be on the line, because in
the end, laws and judges and courthouses don't mean a
(19:44):
damn thing if no one has faith in them. As
the trial got underway, the prosecution called its witnesses to
the stand, many of the same people who testified twenty
years earlier. It was a bit like the reunion of
an old TV show, with the same actors and a
(20:04):
few new twists. There was the neighbor who said he'd
witnessed the murder, the accomplice who said he'd helped Harry
plan the whole thing. And there were new witnesses too,
including Bob Cooley. Bob says he showed up with his
own security detail.
Speaker 4 (20:19):
Well, I guess it was like the mayor or the
rising coming in. They were so worried about my security
because of obviously this was going to be a case
that would be making history.
Speaker 10 (20:32):
It's a very big deal.
Speaker 2 (20:34):
Investigative reporter Carol Marine covered the trial. She also remembers
all the fanfare surrounding Bob.
Speaker 10 (20:41):
They're surrounded by agents. They're in bulletproof vests. They're guarding you.
Speaker 3 (20:47):
They've got automatic weapons everywhere.
Speaker 10 (20:51):
Yes, you are the center of the universe.
Speaker 2 (20:57):
When he finally took the stand, Bob told the courtroom
how in the past he'd been a fixer for Pat
Marcy and the first ward he was in effect a
tool of the outfit who'd been asked to protect when
of their most valuable assets, Harry the hook Alaman. Bob
explained how in the original trial he'd bribed the judge,
(21:17):
Frank Wilson, and how later after the not guilty verdict
came out, the judge had told him, you destroyed me.
Carol was there in the courtroom for this moment.
Speaker 3 (21:30):
You know, Bob Cooley does not demonstrate much emotion at all.
He's got a pretty flat affect. But there was a
point in his testimony talking about really almost forcing Frank
Wilson to take the money in a men's bathroom. I mean,
he choked with emotion and had to kind of swallow
(21:52):
hard and.
Speaker 10 (21:53):
Keep talking.
Speaker 3 (21:55):
Because he knew that he was one of the instruments
of Frank Wilson's demise. He couldn't have been other. Yes,
the outfit ruined Frank Wilson. Yes, Frank Wilson ruined Frank Wilson,
But ultimately all of the players in the surround sound
(22:17):
of that were responsible for the death of Frank Wilson.
Speaker 2 (22:27):
Afterwards, Harry's lawyer had a chance to cross examine Bob.
His strategy from the start was to discredit him, to
dredge up Bob's checkered past. He asked Bob if during
his days as a cop he'd ever been paid off. Yes,
said Bob, He'd taken so called street money that typically
meant tips or payoffs from businesses, you know, like bars
(22:50):
that want to cozy up with the cops. The defense
lawyer kept hammering away at Bob, portraying him as a
shifty and shadowy character. In response, Bob was remarkably candid.
He didn't make elaborate arguments or justifications. He just kind
of took it on the chin. At one point, he said, quote,
(23:10):
I'm not making any excuses for what I did. I
did what I did, but it was an easy way
to get to the top during that time, and I
took the easy route.
Speaker 4 (23:19):
This guy is trying to make me out to be
somebody who's you know, who's a crooked cough passing out bribes.
Speaker 11 (23:25):
Because I guess what he's trying to do is the
classic I'm going to turnish your reputation and credibility. But
the whole purpose of you appearing today as as a
guy who fixes cases in places bribes.
Speaker 4 (23:35):
It's given me credibility in that sense.
Speaker 2 (23:38):
The whole process was tricky for Bob. He wanted to
be seen as the guy who'd cleaned up Chicago, but
in order to do that, he had to admit publicly
to all the most questionable and unsavory things that he'd
ever done. The danger was that these admissions would define
who Bob really was because everyone was trying to make
(24:01):
up their minds about Bob. In his closing statement, the
prosecutor told the jury quote, I'm telling you you have
to like Bob Cooley. You don't have to like him,
but you know what. Bob Cooley faced what he was.
As the jury finished its deliberations, onlookers packed into the
(24:23):
gallery to hear the verdict. Johanna Santanello was there with
the other members of a Logan family, hoping that maybe
finally there'd be justice for Billy. The jurors came into
the courtroom and then the verdict was announced for the.
Speaker 9 (24:40):
Murder of William Logan guilty, and it was like, oh
my god, it's happening. All these years they waited my
aunt and my uncle and my mom to hear that guilty,
and it was finally like a burden was lifted off
(25:05):
of them. Of course, their brother could never be replaced,
no matter, you know, but to see him actually have
to pay for what he did meant the world to them.
Speaker 2 (25:20):
So, according to the Chicago Tribune, when the verdict was announced,
Harry Alamann didn't flinch. He simply blinked his eyes and
stared straight ahead. Harry was eventually sentenced to one hundred
(25:44):
to three hundred years in prison. He died behind bars
after the trial. As reporters clamored for quotes and comments,
one prosecutor proclaimed, quote, this will close the books on
an ugly era in Cook County. It's a great day
(26:04):
for American justice. The one person who was conspicuously absent
at that moment was Bob Cooley. After testifying, Bob flew
off to another undisclosed destination, vanishing once again even so
(26:28):
Bob's presence loomed large in the courtroom that day. After all,
he was the man who'd both started and finished this saga,
the fixer who bribed the judge in the first trial
and then exposed his own trickery at the second trial.
He was a rat or a hero, depending on who
you asked. But one thing was clear. Bob's work in
(26:50):
Chicago is now done. He hadn't expected to survive this process,
but he had. In fact, he was just fifty five
years old. So now what what kind of life could
he really expect? And had it all been worth it?
Speaker 12 (27:24):
Caam driving down a desert highway here? And so you
got to make him turn left, turn.
Speaker 4 (27:33):
In a mile. Well is.
Speaker 2 (27:41):
Dusty and bleak out here. After almost a year of
talking to Bob on the phone, I went to see
him in the obscure little corner of the world where
he now lives.
Speaker 8 (27:55):
You got to make a left up here. Oh, oh, yeah, somewhere.
I think I'm about to miss out here. It is here,
It is okay, Wow, it's.
Speaker 12 (28:06):
Easy to miss.
Speaker 2 (28:08):
Bob lives in a modest house at the edge of
the desert.
Speaker 4 (28:12):
Here.
Speaker 2 (28:12):
He has a small bedroom which he calls his cubby hole.
His bedroom floor is stacked with cylinders of pringles and
jugs of V eight vegetable juice that Bob buys in
bulk to save money. The place looks like what it is,
a hideout.
Speaker 11 (28:27):
Hi are you Rosie?
Speaker 2 (28:31):
Bob has a roommate, a woman named Rosie. When I visited,
she was wearing a house dress with brightly colored, psychedelic
looking flowers. She's actually the one who owns this house.
Bob told me that he's lived with her on and
off for roughly a decade.
Speaker 4 (28:48):
She said, I'm pretty much of a recluse. She said,
I keep to myself or whatever. And I said, you know, well,
I think i'd like to move in. She had no
idea who I was.
Speaker 2 (28:57):
Rosie told me that she knew the broad strokes of
Bob's life, but never asked about the details.
Speaker 13 (29:04):
We don't talk.
Speaker 2 (29:06):
Wait, how come you never talk your roommate.
Speaker 13 (29:10):
He lives his life. I live my life minus with
the dogs back there, and his is in here, so
that's it. He comes in the kitchen. I'm not in
the kitchen. He does all the cooking. I don't do
any cooking.
Speaker 11 (29:25):
But aren't you curious?
Speaker 2 (29:26):
Like he used to work for the MOB as a lawyer.
Speaker 12 (29:29):
Does that make you want to know more?
Speaker 10 (29:30):
No?
Speaker 13 (29:31):
No, no, I don't.
Speaker 10 (29:35):
That's me.
Speaker 13 (29:37):
No, I don't need to know.
Speaker 2 (29:40):
So in some ways, Rosie is the perfect housemate for Bob.
She doesn't pry, though I should point out they did,
in fact talk. They argued more or less constantly during
the time that I was there, not small things like
whether the living room needed dusting or how the pillows
were situated on the couch. Rosie told me that Bob
had messed them up.
Speaker 4 (30:01):
I'm kind of embarrassed, though I hope he doesn't take
a picture of that.
Speaker 13 (30:05):
Kidding, you're embarrassed, Give me a break.
Speaker 12 (30:11):
You guys are a regular odd couple. I gotta tell.
Speaker 13 (30:13):
You we are we if we would be married, I
polly killed him by now.
Speaker 4 (30:20):
Just to get the insurance right.
Speaker 10 (30:22):
Absolutely.
Speaker 2 (30:24):
Eventually, I suggested that Bob and I get out of
the house get some space. So we hopped in my
rental car, and as we drove we chatted. He told
me how lonely he was in the years after he
first left Chicago.
Speaker 4 (30:38):
As I'm driving around, I'm so jealous of people. Look,
I say, somebody with somebody in the car with them,
and I'm jealous. I mean, it's really hard to explain this.
Speaker 14 (30:47):
I'm curious, like, here you are, You're in this town,
you're at this roommate live with you for eight years
and knows nothing about you've got. You said, you've got
no friends in this town. I mean, are you good
with that?
Speaker 2 (30:58):
Are you at peace with that?
Speaker 4 (30:59):
Or are you at the moment at the moment, yes,
you know no, As I said, what are you gonna?
What am I gonna do? I can't feel sorry for myself.
It's such a decision I made, and I suspected it
would be bad, never as bad as I'd got in
terms of, you know, fighting off the loneliness for a
(31:20):
long period of time.
Speaker 2 (31:22):
As we continued driving, Bob pointed out a few of
the local landmarks, restaurants and the like that he told
me he was so strapped for cash that he hadn't
really dined out in years. Bob also showed me the
office of his lawyer, who recently helped him file for bankruptcy.
Bob told me that he'd been living off credit cards
for a while, but then the monthly payments got so
(31:44):
high that they ate up what little money he made
from Social Security, so declaring bankruptcy, it had been kind
of a relief over the past twenty five years. It
hasn't always been like this for Bob. He says that
when he initially left Chicago, he had some money in savings,
(32:05):
but Bob, ever the gambler, had made some risky bets
on the stock market and lost almost all of it.
Bob also co wrote a memoir with a journalist, Hillel Levin.
He made some money off the book, but that was
back in two thousand and four, and in the years
since then, he's been kind of scraping by. It's ironic really.
(32:29):
As a kid, Bob loathed the feeling of being poor.
Remember he hated that his mother had to comb the
shelves looking for dented cans so she could ask for
a discount. This, as much as anything, fueled his ambitions
to become wealthy, to become no tie gold chain Bob
a guy who walked around town with thousands of dollars
(32:51):
in his pockets and now here he was all these
years later, clipping coupons and buying V eight and pringles
in bulk to make his money. Last in the Hollywoo version,
of this story, the Bob character would likely have ended
(33:13):
up on the beach somewhere, maybe down in the Caymans,
but that's obviously not how it panned out for him.
And this got me thinking, what was the ending that
Bob deserved, you know, given everything that he'd done. I mean,
it was complicated. Bob was the guy who induced his
friend into taking a bribe that ruined him, a guy
(33:36):
who helped a murderer walk free, a guy who prevented
a female cop who'd been beaten from getting justice. But
this was also the guy who tried to right these wrongs.
He'd shown tremendous courage. Bob made a stand against the
mob and expose systematic corruption, and the impact he had
in the city of Chicago, it's indisputable. Here's Carol Marine,
(34:00):
the investigative journalist.
Speaker 3 (34:02):
Bob was one of the most consequential witnesses that ever
took the stand in a federal organized crime trial or
probably almost any trial. He did this city and this
state a great service. He risked his life. He did
something that no one else had done. He penetrated the
(34:26):
first Ward and he took down its power brokers. It
was tremendously important in fighting public corruption.
Speaker 2 (34:36):
Of course, Chicago still has its challenges. In twenty nineteen,
the city's longest serving aldermen, a guy named Ed Burke,
was indicted on fourteen counts of racketeering, extortion, and bribery.
Burke went down because another city alderman betrayed him. That
guy wore a wire for two years and made a
(34:58):
series of secret recordings. It was a long con. Seemed
like he took a page right out of Bob Cooley's playbook.
Operation Gambat may now seem like ancient history, something that
happened way back in the eighties, but the ripple effects
are still being felt to this day. There's this concept
(35:20):
in the law known as camouflaging bias. The idea is
a judge takes a bribe in one case and then
to avoid suspicion, punishes the hell out of other defendants
so it looks like the judge is tough on crime.
Then years later the defendant cries foul, says, hey, that
wasn't fair. I got hit with this huge sentence because
(35:41):
this corrupt judge was covering his tracks. And that's what's
happening in Chicago right now. Prisoners arguing that they too
were victims of the corruption that Bob exposed, And so
the story goes on. Some members of Bob's family really
(36:02):
appreciate what he did for the city of Chicago. His
brother Joe, who was an assistant US attorney, told me
that he was proud of Bob's legacy, and his brother
Dennis told me he gradually came to respect what Bob
had done. But it's been trickier with some of Bob's
other siblings.
Speaker 4 (36:20):
I mean, and I have a sister and another brother
who want nothing to do with me. They want absolutely
nothing to do with me. Why do you think that
is because they believe what they saw that I'm some
kind of a rat. I mean, why else would it be.
Speaker 2 (36:35):
I spoke with both of the siblings Bob's referring to here,
Tim and Diane. Both of them conveyed to me in
so many words that they cared about Bob, but they'd
never really been close with him. That even as a kid,
Bob had been unscrupulous, hot headed, and full of himself.
I talked about this at length with Tim Cooley. If
(36:57):
you recall, Tim is the yoga instructor who lives in Vermont.
Speaker 15 (37:01):
I don't know.
Speaker 10 (37:02):
You know, why is Bob Bob?
Speaker 15 (37:03):
You know I I've been thinking about it and and
this may sound weird, but I don't know if Bob
has ever felt loved. I've never known a loving relationship
that he's been in. Actually, you know, he's had a
lot of sex, I'm sure, but I don't think he's
(37:25):
ever been in love. He's never had a relationship that
I've ever been aware of, And so it's like he's
looking for he's looking to fill that lack in some
other ways.
Speaker 2 (37:40):
Tim offered me a take on his brother that was
neither rat nor hero, but something else altogether.
Speaker 10 (37:48):
I'm afraid that.
Speaker 15 (37:50):
That what matters most of all is just that he's known,
that he's known, and the goodness is almost irrelevant. I'm
sorry to say. The most important thing is that, look,
I am a big man. Look I am somebody. I
(38:14):
can do really horrible things, I can do good things.
I'm somebody.
Speaker 2 (38:20):
When I relayed all of this back to Bob, word
for word, to my great surprise, Bob shrugged his shoulders
and said he's right in a sense. In the year
that I spent talking with Bob, he was always upbeat
and quick to laugh. Part of this is just Bob's nature,
(38:42):
but I think he was also kind of selling me
on his story, as if to say, look at me,
I live quite a life, didn't I? And he had.
But when I visited Bob in person and saw his
cubby hole and the roommate who didn't really know him
or cared to know him, I got a different feeling entirely.
(39:03):
Bob's bravada was gone, and in its place was an
air of defeat and almost disbelief, as if he couldn't
quite fathom that this is how things had turned out.
I asked Bob if there was any part of him
that regretted what he'd done, if he could go back
in time, would he have done it differently? Not flipped
(39:24):
at all?
Speaker 4 (39:26):
Absolutely, I mean absolutely. The day I put on that
wire it was all over. I knew it was all over.
I knew that, you know, my life could never be,
But I never dreamed it would be as bad as God.
I'm no better rop than some of those beggars out
there in the street, and I'd better not even think
(39:50):
about it, because again, it is the way it is.
So I mean to say, I wish I could have
changed that are you kidding me.
Speaker 12 (39:57):
I mean, I'm trying to understand how you think about
your own life. If the defining thing in your life
is the thing you wish you hadn't done.
Speaker 4 (40:05):
You've seen my life now. Think about that. You've seen
my life now, and you can't understand how I wished
I hadn't done that. That makes no sense.
Speaker 12 (40:19):
Well, I understand it. It's not that I don't understand it.
Speaker 4 (40:23):
I just.
Speaker 12 (40:25):
Trying to wrap my head around it, that's all.
Speaker 4 (40:27):
But you know, again, I don't know. I'm just saying that.
There's no question in my mind. I'd be an idiot
to say, gee, I'm glad that I, you know, destroyed myself,
and that's what I wound up doing. I destroyed. Bob
Cooley is no longer. This is not Bob Cooley name
wise or even otherwise. What do you mean they left?
(40:49):
Bob Cooley was that person back there in Chicago that
everybody came to when they had trouble and was able
to help all kinds of people and be able to
do whatever he damned pleased, never worried about getting arrested
or getting parking tickets or anything whatever I wanted.
Speaker 12 (41:04):
What is Bob Cooley.
Speaker 4 (41:05):
Now just just to you know, somebody waiting to die.
That pretty much sums it all up right now at
this stage. I mean, they you kidding me? What is it?
He's nobody, he's nothing.
Speaker 2 (41:24):
Hearing him talk like this, I had to wonder once
again why Bob had flipped in the first place. What
had he been hoping for. There were so many different theories,
and Bob himself kind of waffled on this question, offering
different explanations on different days. It was to clean up
the city, it was to heed the advice of his
(41:46):
dying father. He was to stand up to Pat Marcy,
who was a bully. And it's true Bob did not
like being pushed around. But my feeling about all of
these was yeah, maybe, but they seemed like partial explanations
at best. The theory I heard the most was that
(42:08):
Bob owed to the mob. That's what was in all
the papers at the time. But I don't really buy it.
I mean, think about the timeline. Bob flipped back in
nineteen eighty six, he fled town in nineteen eighty nine.
So put yourself in Bob's shoes if you were truly
worried about owing money to the mob, and you were
(42:29):
spooped that some goons were going to break your legs
were worse, Why would you flip and then stick around
town for the next three and a half years. You wouldn't.
It's true Bob was a gambler, and I think that
this does in fact explain what he did. I kept
thinking back to what Bob told me on the very
(42:51):
first day that we talked, that he'd been walking down
the street to get a Deli sandwich, he'd seen the
Prosecutor's office and just walked in on an impulse. And
now I could see it. Here's Bob the gambler, because
walking into that office was, in some ways the biggest
gamble of all. He was wagering his life. He was
(43:14):
betting that he could almost magically save himself and perhaps
the city of Chicago while he was at it. Not
a sensible bet, a real long shot, you might say,
which is probably exactly why he did it. One day,
(43:45):
toward the end of my visit with Bob, we had
lunch together at the little place where I was staying.
I ordered her some pizza, which we didn't finish, and
I was about to throw the leftover slices out when
Bob stopped me, no save those. He told me he
wanted to feed the wildlife.
Speaker 12 (44:03):
Why do you like to do it?
Speaker 4 (44:04):
Because I've been doing it all my life pretty much.
I like to feed the animals.
Speaker 10 (44:09):
Why.
Speaker 4 (44:11):
I'll be rewarded down the road for it.
Speaker 12 (44:14):
It's always something for something.
Speaker 4 (44:16):
I like you. I like animals. You know, I feel
bad when I see him out there. You know they
might be going hungry. It's always been my nature. I
just do it.
Speaker 2 (44:27):
We took the scraps of pizza and drove over to
one of Bob's favorite spots. It was at the edge
of a parking lot next to a strip mall. He
came here often. This is kind of a random spot.
Speaker 5 (44:39):
Why do you pick this spot?
Speaker 4 (44:40):
We're like, we're at a over You'll see them all
over here over on the other side. There, they've got
a fast food restaurant, two fast food restaurants, and that's
where the birds seem to migrate.
Speaker 2 (44:58):
I stood there and watched as the birds flocked around him,
swirling and chirping. For a moment, he seemed genuinely content.
The whole scene reminded me of how back when he
was still in Chicago, wearing a wire. He used to
feed the baby raccoons with no ulterior motives, just a
(45:19):
pure and simple act, a real rarity, because nothing in
Bob's life was ever simple.
Speaker 12 (45:38):
Your herds are up there at the corner, looks like yeah.
Speaker 4 (45:40):
No, they for some reason, they always fly away and
then they come back. But you'll get them cross the
way over here and they'll come back and get it.
The braver ones get fed the most. There's some of
(46:05):
them coming up above.
Speaker 2 (46:50):
Deep Cover is produced by Jacob Smith and Amy Gaines
and edited by Karen Chakerji. Our senior editor is Jen Guera.
Original music and the deep Cover theme was composed by
Luis Garra, with performances by Luise Audrian Terrasas, Alan Fajardo,
Mi Longoria, and Jimmy Messer. Flawn Williams is our engineer.
(47:13):
Our art this season was drawn by Cheryl Cook and
designed by Sean Carney. Mia Lobel is our executive producer.
Special thanks to Heather Fain, John Schnarz, Carly Migliori, Maya Caning,
Christina Sullivan, Eric Sandler, Mary Beth Smith, Brant Haynes, Maggie Taylor,
Nicole Morano, Megan Larson, Morgan Ratner, Royston Deserve, Lucy Sullivan,
(47:37):
Edith Russello, Riley Sullivan, Jen Sanchez, Jason Gambrell, Martin Gonzalez,
and Jacob Weisberg. Additional special thanks to Jill Gillette, Travis Dunlap,
Maggie de Poy, Bill Hogan, David Grossman, Mike Shephard, Jim Wagner,
Denny Cherrillo, Lisa Chase Patterson, and Michael Deutsch. Also Christian McNally,
(48:01):
Isabel Vasquez, Jesse de Bartolomeo, Jane Miliotis, Sarah Kraditch, and
the National Archives at CHU Chicago. I'm Jake Halbert. If
(48:53):
you like this season of deep Cover, then you should
really check out our first season, The Drug Wars, which
tells the story of an FBI agent who goes under
cover with a biker gang and uncovers a series of
clues that leads to a war, I mean, a full
scale invasion. Also check out Pushkin's other true crime podcasts,
(49:14):
Lost Hills and Bad Women. These shows and more are
available ad free for Pushkin Plus subscribers. To find more
Pushkin podcasts, listen on the iHeartRadio app, Apple Podcasts, or
wherever you listen to podcasts,
Host
Jake Halpern
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