Deep Cover Season Two Trailer

Who was Bob Cooley? 

Deep Cover Season Two launches on January 24th. Listen to the whole season early and ad-free by subscribing to Pushkin+.

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Episode Transcript

Speaker 1 (00:15):
Pushkin. As far as I'm concerned, I'm a dead man
right now. This is Bob Cooley, or I should say
this was Bob Cooley when I say I'm dead, Maybe

(00:36):
not even physically dead, but I'm dead in terms of
Robert Cooley no longer exists. It all started back in
the nineteen seventies when Bob was a lawyer in Chicago.
A powerful mobster asked Bob to fix a case, a
murder case, so a hitman could get off scott free.
If you say you can do it and you can't,

(00:59):
that could be a problem. I know what that means.
It means you get an extra hole in your head.
It turns out Bob was really good at fixing cases,
and he did it for years until one day he
decided to switch sides, go over to the FBI, and
betray the mob. The moment I put the wire around

(01:19):
the first time, my life was over. I couldn't ever
practice law anymore. I couldn't never stay in the city anymore.
Bob could give us judges, lawyers, police officers, politicians. He
could wire up against those people and go be Bob Cooley.
I would come into the office in the morning and

(01:42):
if he didn't call me right away. I didn't know
if he was in a trunk somewhere yet. If it
ever got out, they would kill me in a heartbeat.
Or approximately five years, a Chicago lawyer has been a
government informants, secretly recording conversations with some of this city's
more than shakers. If you're wondering why would a guy

(02:03):
like Bob Cooley just decide to flip, well, you're not alone.
I've wondered the same thing myself, and I've talked to
FBI agents, federal prosecutors, and former mobsters. Many of them
are still wondering. Who was Bob Cooley? Really? I wouldn't
trust that guy. He looks like a little scum, big layer,

(02:24):
stool bidgi. He looked like what he was or at like,
is this guy for real? From my perspective, Bob was
too good to be true. There's got to be something
wrong with this. I can say with all certainty. I
think he's a hero because he didn't have to do
what he did, and he did it anyway. Is he
a plant? Is he a double agent? What is he?

(02:45):
I'm Jake Halbern and this is deep Cover Season two,
mob Land coming January twenty fourth from Pushkin Industries When

(03:08):
it was fun. Subscribe to Pushkin Plus and you can
binge the whole season adds free. Find Pushkin Plus on
the deep Cover show page in Apple Podcasts or at
pushkin dot fm, slash plus