Episode Transcript
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Speaker 1 (00:02):
When people ask me, what are your brothers like? I
turned my head and smile. How do you say camp fires,
American trucks and wet grass. My brothers are w d forty,
cast iron gates and thermal underwear. They're broken windows, shell
casings and swinging screen doors. Ryan is my twin, Dylan
(00:26):
is my opposite, but on the right day, we're the same.
I want to tell you a story, a true story,
but truth is always based in opinion, and who's to
say that we're telling the truth. Welcome to The Dougherty Gang,
a production of I Heart Radio and Katie Studios, Episode
two fifteen in the Morning. I'm Courtney Armstrong, a crime
(00:49):
producer at Katie Studios with Stephanie Lydecker. We've been working
with producer Beth Greenwald on The Dougherty Gang for months now.
The three siblings have agreed to tell their story for
the very first time, each from separate prisons. Lee Grace
Dockerty is at Federal correction Institute Aliceville in Alabama, Ryan
is in United States Penitentiary Tucson in Arizona, and Dylan
(01:11):
is at the Federal Corrections Institute in Bennettsville in South Carolina.
This call was from the Federal prison. Me and Dylan
were just looking at each other like in a state
of shock and surprise. If Dylan is under anxiety, you
know that I'm going to be under anxiety, because Dylan
is usually a very cool, calm collected person. I felt
like everything was really stacked against us, you know what
(01:33):
I mean. And I just felt like he was just
unfair from the start. On the afternoon of August one,
two thousand and one, twenty one year old Ryan Dougherty
came home from court, met with his probation officer and
found out he was in a situation where he would
soon be sent to prison, away from his son, who
was days away from being born. Here he is speaking
with Beth Greenwald, and so now this guy's at your
(01:54):
home and he's telling you all these things in these threats,
and is Dylan there. It was with the little shorty
a k because he had put the majority of the
firearms in there. And the guy goes over and jiggles
it because it's got a log chain through two holes
that are bored into the doors of the shed. And
I'm already of the mind pretty much we're gonna rock
(02:15):
and rolling it out of here. The guy gave it
a mighty little job, and he you know, he came inside.
He's like, hey, you're gonna did you give me a
key to dad or open it for me or whatever
some some ship like that. He leaves, and what happens, Yeah,
he leaves, and then we started talking about things. And
then my baby's mother tells my brother and sister. She's like,
holy shit, I can't believe my fucking ears of what
(02:37):
this guy just threatened. Feeling he was out of options,
he and his siblings, twenty nine oldly Grace and twenty
six year old Dylan, we're grappling with the reality they
were facing. Here's the Grace. I think all that stress
was coming out, and he was coming out in negative ways.
And I think Dylan, being the older, protective big brother,
was looking at this as a short term solution of
(03:00):
let's run from the problem because the base officer does
not want to work with Ryan. I wouldn't say I
was thinking clear. It's hard to explain, but also stars
had aligned. It was like the gravitational pool was just
that's what it was. It was just a really bad
situation for our family. All we knew about prison is
from what we have seen on TV or movies. We
basically thought, okay, well you go to prison and you die.
(03:23):
So with us going into that with that type of fear,
that type of anxiety, we basically thought that any time
in prison is a death sentence. You know that. There's
the state of mind that we were in. We didn't
know any better. You know, nobody in our family had
ever been to prison. With the strict mandate the probation
officer was laying out, Ryan felt like he was in
an impossible situation. The probation officer comes to your job,
(03:45):
and Florida's the right to work state. Your probation officer
comes to your job, and your job's like, yo, you're
on probation. Man. We don't want to deal with this
ship or somebody like you. You're fired. You're like, bro,
if I get fired, I'm going back into prison. Ran
just felt like he couldn't do the probably Asian, there
was no way with him having a newborn baby. How
was he going to facilitate childcare? How was he going
(04:06):
to drop in that school. There were so many questions
that we didn't know, and it just seemed impossible to
work around all these rules. After the probation officer left,
anxiety and fearmounted and Lee Grayson Dillon met up with
Ryan at his house to figure out a way to
protect Ryan and keep him from being sent to jail
for fifteen years. We were all at the house. We're
sitting down. I'm writing shoot on paper because I'm dumb
(04:28):
and paranoid enough to think that the fucking ankle bracelet monitor,
I don't know if it's got like a microphone on it.
That's how young and stupid I was, and like fucking paranoid.
That's that's how bad my thought process was at that age.
We were sketching it out. We would go back and
forth and kind of trying and figure out what seemed
like something iron and for plotting. What we were plotting
was relatively calm about it. So we sit there, we
(04:51):
scotch out a rough plan and that was it as
I sit now, granted up had ten years to think
about it, But my brain works differently than did that right?
You know, you can very a very basic litmus has
is just to say things out loud and if they
sound stupid, maybe don't do them. And for that one,
it was just a dumb fucking idea. How long did
it take for the plan to come into fruition? Was
(05:13):
in a ten minute conversation? Was it an all night conversation?
It was pretty much all night because I know, I
was laying on the couch and I'm talking. Ryan's next
to me, Dylan's pacing, so it was just everything was
just happening so fast, and Ryan was just upset. He
was shaking. It would go from anger to grief to sadness.
(05:33):
You know, I felt kind of traumatized from the whole
ship and I just snapped. So yeah, I wasn't exactly
thinking right, and I was at the point where I
was almost just happy, just happy that you know this,
this will force a resolution. Hopefully somebody will pay attention
once they've seen this fucking bomb that went off. Here's
Dylan again. You know, we're just gonna do this. X
y Z will get that, and then we'll be gone
and everything will be all right. You know. The playoff
(05:55):
was really fluid, but you know, Ryan's girlfriend was going
to come down south and meet up with us, and
the US settles will this will will be. The wheels
began to turn and an off the cuff plan was hatched.
Early the next morning, the siblings would pack up and
head to Mexico, where they'd start fresh. Ryan would send
for Amber and the baby once they got settled. The
timeline was very last minute, because at no point did
(06:17):
we ever look at each other and say, let's get
in the car, let's load up the guns. Our plans
were actually to stay under the radar, not just from
the probation officer, but from anybody that was trying to
track us. I'm not gonna say it was like blind
in my rage, but I was like I was blinded
by you know, just kind of me in that corner.
You get to a point, I guess all people probably
(06:39):
have it where whatever you do snap, it's it's very
hard to come back to making like rational decisions. I
just snapped in like a big way. Older sister Lee
Grace wanted nothing more than to help a little brother
out of the situation. I think he was under so
much stress that my brother Ryan, he did not know
what to do. You know, he's a young man, this
(06:59):
is his first baby. He was under a lot of
pressure from his baby's mother. I've sent some text messages
that were inappropriate. If it was that bad. Why did
you just give me probation? The judge in court saying
in my transcripts, he's like, I'm sorry, I'm lumping you
in with four year olds at rape eleven year olds,
But unfortunately our legislator has no difference. He has. Dr
(07:19):
Avidan Moleski. He's a PhD and associate professor who specializes
in complex family difficulties and developmental psychology. He's also the
author of Sibling Issues and Therapy. Dr Mlevski followed the
doctor case closely. Here he is speaking with producer Beth Greenwald.
When this story first broke, What were your initial thoughts
on this family, these siblings? My first knee jerk reaction
(07:44):
to when you hear a story of three a young
adults driving around violently, shooting at cops across several states
and bank robberies, and right, your first initial reactions, these
are criminals, let's go get them. What's sad? And more
of a rational part of my brain kicks in and
considering that it was a sibling story, I started reading
(08:06):
up on this case a little bit further, and then
as a story unfolds and more information comes around, and
then I started realizing that It's much more complicated than
the black and white of the good guys and the
bad guys when you really look at the crime involved
and how they were sentenced and how they were treated
even initially. Why Ryan had to be registered as a
(08:29):
sex offender, that whole story of how it developed is
a system failure. These siblings, the entire system failed with them.
The only system that did not fail them is the
sibling system. It was the only system that took care
of them, the sibling dynamic that they had. And let
(08:49):
me ask you something. This thing that happened was going
to destroy the rest of his life for all intensive purposes,
register as a sex offender, ankle monitoring device, all these things,
And did you feel like, just in your opinion, if
something had been broken down a little bit, if things
had been explained, if he wasn't looking at fifteen years
in jails for sex thing? You know, was that a
system fail as you said, or kind of unpack that
(09:11):
a little bit if you don't mind, you have to
register as a sex offender equal to someone a fifty
year old perfort who raped a kid in a yard.
They are registered in the same registry because as a
nineteen year old he sexted someone who thought it was fifteen.
Now we're obviously not condoining that behavior in any way,
(09:31):
but do we really equate the actions of the nineteen
year old that was basically sending a loot text to
a rapist? We can now again legally we do. And
that's part of the failure here. He did something far
less severe than that, and that really spiral this in time.
That's what got this entire story going. So when I
(09:52):
say it was a system failure, this is one of
the kegs that failed him. Here's Ryan speaking with Beth
green Walt. Would you say it was Serve Bivle mode?
Panic mode? You know your panic, and when you panic,
you don't think Clark directly when it's a situation like that.
I mean, I don't know how clearly they were thinking.
I don't know the thought process. I mean, I know
in my whole life from my brother and sister, it's
(10:13):
just difficult to say what was going through their head.
I mean, as they were older than me, not carry
guilt around with me, and I'm probably well for the
rest of my life even though they tell me not to.
Eventually I ruined their whole life and it's just hard
to live with that. Frank Kazinski is the owner of
Tampa Bay Monitoring. His company has been providing alcohol and
(10:34):
GPS monitors for over a decade. He shared his thoughts
on how Ryan's probation was structured. In his case, he
was given this bracelet with the idea that one he
was responsible for paying for it. And I'm guessing, and
I don't know this for a fact, that he was
placed on some form of house arrest, which meant you
(10:55):
had to keep track of everywhere you went if you
had anything any except pations that had to be approved
by a probation officer or some authority. And in this case,
also you have to make sure you kept up the payments,
Like you gotta go to like meetings like three times
a week, and you gotta pay like twelve a month
to beyond that probation. You know, I'm pulling in like
(11:16):
a month, So you want to under of that, and
then you want me to sucking be at this place
at that time. By like as soon as I tell
my job, hey, I can't work today, I have to
go to this meeting, they're gonna be like, yeah, we'll
find another employee. It's the right to work state that's
a problem. There's jurisdictions such as Tennessee that the state
literally will pay for the bracelet if you can't because
(11:39):
they figure it's a cheaper way of number one avoids overcrowding.
Two that allows you to keep your job. Three you
sleep in your own bed with your family. Mommy and
Daddy are they're not in jail in this case. They
basically told him that he was responsible for paying for
this thing and he couldn't do it, and they didn't care.
(12:00):
It was basically being set up for failure. People charge
anywhere from eight to fifteen dollars a day, and I mean,
I don't know too many people can pay fifteen or
you know, sometimes ten dollars a day plus a deposit
or whatever else is necessary. But why they insisted on
a payment here when they know the guy you didn't
have the pot or the window to throw it out
(12:21):
of his is nonproductive. Ryan was feeling hopeless as he
processed what this one mistake from two years ago would
do to the rest of his life. Once you get
a felony, you're fucking pigeonholed into a goddamn mediocre job
and a mediocre life and like just barely making it.
Go figure out what the minimum wage's in Florida at
the time when I was there, it's like fucking eight
dollars or some ship. Go figure out what rent costs.
(12:44):
Go figure out what food costs. Figure out what a
car payment costs. Are out the cell phone payment costs,
figure out what insurance costs. There's no way to cover it.
You know, you get to a point where you're just
sitting there and you're like, well, what is the point
of me even being alive anymore? You know, what's the point?
What could I do? The deathbed promised Dylan made to
(13:04):
his dad to look out for his little brother with
something Dylan took very seriously. He felt powerless, and as
a result, his frustration intensified. The part that really, you
know bothers me is we've all made mistakes. We've all
done things that we maybe regret a little bit or
or a lot of it later. I'm not saying everybody's
committed a felony. You know, my brother made an automistakes
(13:25):
as a kid. It's just another one of those things.
It's like not unfortunate advance the way that at all unfolded.
It was like we were all on pins and needles.
I could just see anger Dylan and just build with
his anger. It's just coming out of him. And it
was just a really anxious time. Lee Grace was struggling
with her addiction to drugs and was coming off the vendor.
The situation was forcing her to quit pills cold Turkey.
(13:47):
I don't feel good. I need my kills, and they're
basically saying no, you don't. You know, so I don't
have any pills with me. I don't have any drug footsoever.
So you know, all my zanex are gone. I'd eaten
all of them. We're going to take a quick break here.
We'll be back in a moment. The plan was to
(14:17):
try to get some sleep and leave first thing in
the morning. I remember I was extremely drowsy. I had
only slept for about four or five hours, and I
got up and it was early in the morning. I
just remember being on the porch and looking and I'm
looking now and it's it's very bright and everything is
just kind of happening. But I'm just physically there. I'm
not my emotions are just somewhere else. I was almost
(14:38):
kind of emotionally shut down. But I remember carrying things
and putting them in the back of the subaru, and
I'm just looking at Dylan and I'm just following him.
I'm just trying to kind of gauge how everything is
gonna happen. But at the same time, you don't know
something bad is going to happen. You just have a
very ominous feeling. As the Doctrity has packed up the car,
it was obvious their plan came from a place of panic,
(15:01):
not common sense. The siblings weren't prepared on any level
for the journey ahead. You're not gonna be honest with you.
I don't even think we packed any food or water.
You know, later on down the line, we thought we're like, hey, man,
we should probably get a water bottle, just a really
simple water bottle. At one point, I was going back
and forth. Am I gonna go with them the whole
(15:22):
way to Mexico with them? Or maybe I was going
to stay with Amber because you know, she's about to
give birth to this baby, and I wanted to be
there for my nephew and help out with the baby.
And even if it was only in my own head,
I was thinking, well, maybe I need to stay with
Amber as you know, her older sister, or you know,
to look out for the rest of the family that
(15:44):
we would be leaving behind. Um. Now, when I got
in the car and um we we left, that's why
I decided, well, this is this is where I'm at,
This is I'm going to continue to stay with Ryan
and Diylan because they need me. I think we knew
we should need the money before we left Florida at
that point, you know what I mean, it was it
was just a whirlwind. I had so many tools. I
(16:05):
probably could have you got on the arnet and had
a you know, on eBay and had a yard sale
and come up with dollars. In retrospect, it's easy to
see that selling the tools would have been a smarter
plan than packing up the guns to sell. We were
going to cross into Mexico once we had cash, because
we didn't want any credit cards. We didn't want any
(16:25):
ties to where we were going. The docertees didn't have
much money on them and they knew they would need
cash to make it to Mexico undetected. We actually had
my brother's guns and he was going to sell them
to make money. Dylan's friend was going to purchase the
guns from us and give us cash. I feel like
(16:46):
I did, would uh, you know anybody? We do as
far as you know, maybe not as going to the
degree that I carried in, but I know the great
set of shumen. On the other foot, I wouldn't even
have to ask something on They would have been there
for me just as much as I was there for Ryan.
And Ryan loving Amber the way he did. If he's
separated from someone he loves, he's going to go off
(17:06):
the deep end. So a lot of his thought process
was what do I do without my baby's mom? What
do I do without the baby? So you know that
really factored in. It was harsh. It was very harsh
on him. He was very sad, He was very lonely.
You know, he was expressing a lot of distress. Amber
was due to give birth in a matter of days
(17:26):
and it crushed Ryan to leave her. Here again is
Ryan speaking with Beth greenmalt So you knew it was
a son before you left, correct you guys found out
the sex of the baby? Yeah? I did. I went with.
I took off of work. You know what, man, it
was the weirdest thing that would make her happy. Man.
She was just so happy that I would be willing
to take off of work to come, and I'm like
taking her myself. I'm like, man, she's crazy if she
thought that she could keep me from coming to go
(17:48):
to the ultrasound, whether to see if it was a
boy or a girl. I had a ritual with her.
I would always come back in and uh, kids her
goodbye before I went to work. I'd leave, I get
all the way out, and I have like a little ritual.
I'm all the way back in the house and I
pull the cover down just a little bit because she
always goes back to bed because I get up so
fucking early to work, and I always give her a
(18:10):
kiss and I always tell her I love her, some
thing I would always do before I went to bed,
and uh, I got to go back inside. She's all pregnant,
belly and big and standing on like the front stoop
on the inside crying, you know, And I told her
I loved during goodbye. Driving away, I drive about fifteen
miles away from the house. Twenty miles away from the house,
(18:31):
I'm like, ah, I can't have this ankle pricelet no
more cut it off. I wrapped it up with its
box neatly, and I said it nicely on the side
of the road in a place where they could easily
locate it and get their ship back. Once you line out,
of course, and you commit yourself to it for some
things that you just can't take back. You know, once
you cross that rubicon, you're just fucked like you to
that cause and you've got no choice but to see
(18:53):
it through. Here's some additional inside from dr Abbadan Mileski's
conversation with Beth Ryan. Obviously commit a crime two years
earlier than the start of this quote unquote crime spree,
and he was labeled as sexual offender, and he's the
first to admit and take ownership of that what he
did was wrong. But he was eighteen or nineteen and
he sent sexually an appropriate text to a minor. Now
(19:16):
a nineteen year old is not functioning completely in terms
of decision making. Our magic reaction is, oh, he's a criminal.
That's it. Either he's got a rap sheet already. And
we think in this black and white way when it
comes to cool criminals, when you start puling white, and
I think this story is a window into this larger
(19:37):
issue of how do we deal with quote criminals, and
we just boxed them all in. And this sex registry
is the greatest example of that. But socially, psychologically, developmental, psychology, neurologically,
it's a whole different story. So again, the system, many
systems failed them, except for the symboling system. And let's
go back a little bit, because you know, their father
(19:59):
really instilled in the children from a young age the
importance of family. So how does that land. You know,
in that family dynamic, they were clearly a close knit
a bunch of siblings, and then you add all these
stressors to it, and that closest just survives even further,
and that sibling closeness or that sibling compensation is kicking
(20:22):
in now in a very powerful way in order to
help the siblings continue working together to deal with this
new life adversity. The Doperties were looking forward to a
fresh start. Unfortunately they did not foresee what would happen next.
We're only in the car about maybe twenty minutes, maybe thirty.
You know, we had just gotten in the car and
(20:44):
I had just we had just come from the gas station,
and I was very drowsy. I was sleeping on and off,
and as soon as the cops got behind us, That's
when I immediately woke up and realized there's a problem.
You know, I'm looking at Dylan, well what are we
gonna do? And you know, we're all in that state
of panic. I think when the cop um when he
(21:04):
put his lights on. I don't remember if he actually
put the siren on, but I do remember him putting
the lights on, and at that moment, you know, it's
like seven or seven fifteen in the morning, I thought, well,
there's no turning back now, because now the police are involved.
At any point before that, I think we could have
made a different decision. We could have gone a different
(21:26):
way and the police would never have gotten behind us,
and we would have just had continued our merry way
to getting rid of the guns, selling them legally and
getting the money and just leaving the United States. Remember
somebody asking, you know, hey, are you are you gonna
pull over? Or you know, what are you gonna do?
Was there ever a moment where you thought about pulling
(21:48):
overt from like the first little bit, I have an
asshole lo the guns in the car. I'm a convicted felon.
I just caught off my ankle brace that monitor for me,
that ever got crossed as soon as I cut that
bright set up and a cop pulls out and Cherry's
up pops his lights on me. Here's Detective Kevin Widner.
(22:12):
At the time, he was an officer on the Zephyr
Hill Police Department. Here he is speaking with Beth Greenwald.
I would love to hear from your perspective what you
remember about that day and how it started for you
and what happened from there. Started out like any other
day for me. I just went and I got my
cup of coffee, and then I was going to run radar,
do some traffic control. I set up a sixth street,
(22:33):
which is a one way street and Zephyr Hills speed
limit was thirty through there. And as I was running
and car passed me doing and pulled in behind it
turn on my lights. I knew they wasn't going to stop,
just based off the way that they was acting. Let's
(22:53):
stop here for another quick break. We'll be back in
a moment. The docertees wanted to fly under the radar,
but less than thirty minutes into their ride to Mexico
did engaged police and I'm like, well, funk I can't
pull over, So then I take off and I started running,
(23:14):
and then they made a right hand turn onto fifty
four from sixth Street, and as soon as they made
that right turn, they started shooting at me several rounds.
And then at that point again that I pursued them,
there were still more shots being fired from the past
or side of that vehicle. Whoever was in in that
(23:36):
fast seat, it was still firing at me as we
just one down fifty four. It was just me at
that time. I didn't have any backup unit, so I
tried to keep some distance between us, just keep a
little bit of visual on speedis were about a hundred
miles are a little over. With his focus on his
family and his future, Ryan made a life altering decision
and a split second wasn't personal. It was between me
(23:58):
and my freedom. I did what I thought I had
to do. From a lack of good options came a
shitty option. We were not that the type of family
to physically harm somebody, because we know what physical harm
can do to somebody's body. You can become paralyzed, or
you know, you could end up in a wheelchair. So
(24:20):
in no way, what do we actually aim a gun
at someone's physical body. From the sound of it, I
thought that they sprayed the whole side of my car,
but actually they just got the front driver's side tire.
Speedes went back up to about a hundred miles per hour.
My front tire was flat, so I couldn't keep up
with them safely. At that point, Officer Widner had vowed
(24:42):
to protect and serve and he was not going to
be deterred right away. It's game on. They are obviously
a danger. If they're gonna shoot at me like that,
then obviously they're a danger to a citizens. So we're
going to do what we need to do to stop
that threat. At the end of the day, I made
a plan. It was shitty. It was take enough money
to get out of country, to be somewhere that doesn't
(25:04):
have extradition treaties, and to try and start a light there.
It wasn't a good idea. It was never a good plan.
It was never a good idea. But I didn't think
well when I was that age. As soon as I
come around the corner and I see a muzzle flash
from the a K and it's one of those old
ship moments. And to be honest with you remember being
woken up out of like a cold sleep, just hearing
(25:25):
like some hell on wheels behind anything with the motor
and some wheels in a car probably outran the cops
a hundred times. I did not get this tag number
right off the bed. Also, I knew it was an
out of state tag. End of the car that was speedy.
Anything north of a hundred is a pretty good clip.
But for me, like you know, I'll hang out of
like a hundred twenty or a hundred thirty on the
(25:46):
interstate and think nothing of it. They was showing total
disregard for everybody's safety. Pull it over as an option.
It's too easy in that area to hit some left
and rights on him and disappear people. They're like, you
cannot run the radio. Bull it. More on that next time.
The Dougherty Gang is executive produced by Stephanie lie Decker
and me Courtney Armstrong, along with Beth Greenwald, Sean McEwen,
(26:09):
and Joseph Morgan. Editing and sound design is by Jeff Twa,
mixing by Peter Nay. Additional producing by Chris Graves and
Jeff Shane. The Doctor Gang is a production of iHeart
Radio and Katie Studios. For more podcasts from my Heart Radio,
visit the I heart Radio app, Apple podcast, or wherever
you listen to your favorite shows.