September 20, 2021 • 25 mins
On August 1, 2001 21-year-old Ryan Dougherty appeared in a Florida courtroom to plead no contest to felony charges for a crime he committed as a teenager. No longer the person he was back then, Ryan was looking forward to the future with his pregnant girlfriend who was due to give birth to their son in days. After court, Ryan met with his probation officer and was shocked to learn he had 48 hours to comply with the terms or he’d be sent to prison for 15 years. Distraught, Ryan confided in his 29-year-old sister Lee Grace and 26-year-old-brother Dylan. As the hours ticked by, the trio felt the only way to save Ryan from prison was to run.
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Welcome to the Docerty Gang, a production of I Heart
Radio and Katie Studios. Docr To Gang is the true
story of three siblings. Twenty nine year oldly Grace, I'm
the oldest. We have a very, very loving family. Our
family is very accepting. If you make a mistake, our
family will shoot you out and they will quickly open
their arms. Twenty six year old Dylan. I wish it
(00:22):
had not happened the way, and I wish I had
never been put in that position. And obviously if I
could go back, I would change a lot in twenty
one year old Ryan. I'm not good at covering my track.
I'm not good at lying. I'm not good at being
a cheater. And I'll even'll wake behind me like a
mile wide. The three went on an eight day fifteen
state Crimes free in two thousand eleven that rocked the country.
(00:44):
They liked the notoriety, They liked the fact that they
were on the Monday, liked that they were getting national attention.
That just played in the hole, you know, Bonnie and Clade.
They went from wielding an eight key forty seven while
trying to outrun police in Florida. The police tried to
pull the sibling Joe the first speeding, but instead officers
say the Doherty's pulled out a gun firing December twenty
(01:06):
shots to robbing a bank in Georgia. What do you
get out of it? You get federal charges, you get
to FBI chasing, and you're gonna get your picture taken
to leading police on a high speed car chase across
Colorado ending in a shower of bullets fifty But that's
(01:26):
not where the story begins ten years, because we're coming
up in ten years and I mean, we've done thirty years.
This is the Dockerty Gang Episode one. We can't change
the past, not yet. I'm Courtney Armstrong, a crime producer
at Katie Studios with Stephanie Ledecker. We've been working with
producer Beth Greenwald and The Dockerty Gang for months now.
(01:49):
The three siblings have agreed to tell their story for
the very first time, each from separate prisons. Lee Grace
Dockerty is at Federal Corrections Institute Aliceville and Alabama. Ryan
is in the United States Penitentiary Tucson in Arizona, and
Dylan is at the Federal Corrections Institute in Bennonsville, South Carolina.
This call was from the federal prison. The last time
(02:10):
I spoke to my dad. I don't know if you
ever talked to anybody on their death bed, or had
anybody that you know asked you to do something while
they're trying I guess, but it's the definitely weighed on me.
You know, it was something that I really later on
took the heart. They didn't say, you know, respect your mom,
or do good in the school, or be nice to
your sisters or anything like that. You told me the
last thing I remember him telling me he was looking
out for your little brother. I don't know if he
(02:32):
knew and was going to be right there soon, but
he thought about four hours after that. That's older brother,
Dylan Dougherty. He was just twelve years old when he
made a promise to his father on his deathbed that
he would take care of his little brother. It would
change the course of Dylan's entire life. Here he is
speaking with Beth Greenwald. Family always seems to be the
most important thing to all of you guys. Is it
(02:53):
because you lost your dad? It was just the way
that you were raised For my dad, you know, family
was everything, and that's definitely where I got those ethos
from from him. You know, family, trump's all. No matter
what happens in your family is always tiring. Do you
think things would have been any different if you're if
your dad hadn't passed That's a big question. But John Daddie,
I think things would be a lot different if my
(03:13):
father had passed away. Their story was covered in the
national media and it made us want to know more.
This man hunt has been going on for more than
a week. Harmed, dangerous, and all in the same family
that led to a twenty mile long chase at speeds
of over a hundred miles an hour. Are they three
goldenhearted siblings willing to risk everything for each other or
were they just looking for notoriety. My brother is going
(03:37):
to be on the run. I'm going to be on
the run. I'm on probation, and I burned all my bridges.
It's a really strange feeling to be untethered. You don't
have anything that means anything to you anymore. You've lost
everything that matters. You can't go self surrendered. That doesn't matter.
You're still gonna get the same amount of time you're
gonna get whether or not you keep going from There,
feature film based on the cross country crime spree set
(04:00):
to be released later this year. Here's the movie's writer, director,
and producer Sean McEwen, who's known the siblings intimately for
eight years. The Doctor He's grew up in a small
house in La Couchee, Florida, located about fifty miles outside
of Disney. Mom Barbara was a nurse, and dad known
as Doc, worked in construction. And five kids in seven years, Lee, Grace, Dylan, Devon,
(04:21):
Aaron and Ryan growing up. The key lesson they instilled
on their kids with family first and loyalty is everything.
Youngest Dockery, Ryan talks about their mother. My mom went
crabbing and fishing with me. My mom took me places,
my mom did ship with me. My mom careen love
for me. My mom tried real hard, but we were
just really willful kids, like I'm gonna do what I want.
(04:43):
My mom was always a worker in the family, like
my father did construction and demolition and stuff. But honestly,
I think that my mom's payout class tis and my
father was able to kind of be like more of
a stay at home father with us kids, which was
a blessom. Here's oldest sister Lee Grace. Kids. We were
not the best of children. We are really bad. We
saw you know, we had behavior problems in school. If
(05:03):
we did get in trouble, you know, sometimes even my
dad would laugh at off. So we were raised strict,
but not maybe as strict as other kids. Ryan's always
been the baby of the family. You know, when you
grow up as the youngest child. Me and Ryan have
seven years age difference. He was the type of kid
that everybody just gravitated toward him. He was like the
golden child in our family. He was easy to love
(05:26):
and he was just so easy going. If we laughed
at a joke, he laughed. He just wanted to be
like the big kids. You know. We could be hungry,
We could be spending our last ninety nine on a
Hamburger and he would split it with me. Everything with
Ryan is fifty fifty. He wants to be able to
share things. He's so generous. Dylan was not afraid of anything.
(05:48):
He was always there to protect us, even at a
young age. I always looked at Dylan like he had
this like hero complex. He always wanted to save somebody,
even as we were adults. It was always like I
knew I could do whatever I wanted because I knew
that John was there to protect me. You know, I
could say whatever I wanted, I could fight with anybody,
and my brother was always going to back me up.
(06:09):
You know. It was like my my protector. Even though
he's two years younger than me, I looked at him
as my equal. Here's Dylan. When he was a child,
his father wanted the best for him and felt he'd
have a few more opportunities living with his aunt and
uncle while still staying close to his siblings. Dylan was
legally adopted by his aunt and uncle, who he refers
to as stepmom and stepdad. I would say definitely a
good older brother. I just imparted all of the called
(06:32):
the wisdom that I received from our father and from
my stepdad and even my grandfather. My mom had five
kids in seven years, so there's not a whole lot
of space in between her, so we were all relatively
close to the same age. I think I was kind
of cool growing up. We're all kind of at the
same point in life together. So while the Doctuli's had
fun and leaned on each other during their childhood, things
(06:52):
were tough there wasn't a lot of money, and things
got even tough when once dad died. The siblings were young, Lee,
Grace was bull you dealing with s twelves, and Ryan
just seven years old, So it was hard on the
kids and possibly even harder on mom. The death of
father William Dockerty known as Doc, was tough on everyone,
especially mom Barbara. She was left with five kids to
(07:14):
raise on her own. So my dad was very young,
he was only forty one years old. My mom was
left with all of us kids. Everything fell to my mom,
all the discipline, all the finances, and it was very
difficult for her, you know, because my dad was the
love of her life, her soul mate, so she was
going through losing her love and then also the father
of her children. And that made it really, really difficult
(07:37):
because my mom really had nobody to turn to. Her
family was very distant with her, so they weren't with
my mom's you know, nobody had my mom's back at
that point. She was by herself. She did everything on
her own. She always said the same thing, your father
is my best friend. I cannot live without him. So
I think that was a point where my mom realized
(08:01):
the person that she loved most of the world had
passed away, and I think it really really affected her,
you know, I think even more than she than she
put out there, because she was just struggling. He had
nobody to turn to. At this point, everyone was doing
the best they could. Older brother, Dylan, the one adopted
by his aunt and uncle, had his sight set high
and was on the straightened arrow. When I went to
(08:22):
ninth grade, my mom started home school met uh did
homeschooling for about a year and then enrolled in the
community college. And I went to school for a few semesters,
and then I just thought it did death really wasn't
what I wanted to do. I started working young don't
drive into construction and started making money and doing a
grown man's job when I was sixteen. And I was
making a grown man's paycheck at sixteen and was living
(08:43):
at my parents house, so I had funny of money
to spend. Lee Grace was living a rougher life, CouchSurfing
at various friends places, often with her younger sister Aaron.
We were like gypsies. We were from here to here
to here. You know, we moved so much. I probably
lived in about twenty different places, so there wasn't really
one address that I was using. I was just kind
of going, you know, by the seat of my pamp
(09:06):
and my sister would be there with me. Aaron and
I were going from family friends to our boyfriend's apartments.
We were fourteen and fifteen, so that was a direct
result of my dad's coffee. It was right after a
dad died when Lee Grace went off on her own
with her sister. Things were tough at home. Her relationship
(09:26):
with Mama's volatile, and the only way Lee Grace could
deal with grief and guilt was to get out of
the house. I wasn't dealing with my dad's death very well.
She wasn't holding up her end of the bargain, and
I always I felt so much blame and so much
guilt for my dad dying because I was the oldest child,
and heart attacks are paused by stress, and you kids
stressed your dad out, and now he's dead, and what
(09:48):
are we gonna do. We don't have any money. Dad
didn't leave a will, we didn't have life insurance, so
it was like, you know, you're fourteen years old, You're
worried about getting your drawer's license, and going to up
dances and problems, and now I got to worry about
biblings and my mom. This chaotic living situation Ledley Grace
to drugs, stripping, and never holding down jobs for long.
I never was able to stay in the same position
(10:10):
for any amount of time, because when you're in that
phase of your addiction, it's very hard to get up
in the morning. You're not cooked, you're working when you're hungover,
or you're coming off a bad high, or you're coming
off a binder. So basically I had explained my situation
to some of the people that I work with, and
they basically said, we understand, thank you for telling us,
but you need to go home and come back in
(10:32):
a year when you've got your mind right. And instead
of taking that advice, I basically quit the job. Leaving
the traditional nine to five world would impactly Grace for
years to come, enabling her drug habit and driving her
deeper into addiction. And I went right back to dancing
because they don't care. You know, you come in at
six o'clock at night, seven o'clock at night to start
(10:53):
your shifts. They're not expecting you to take a drug test,
you know, they don't care a futurine Jewish pokes. You know,
you could do whatever you want as long as you're
making me quients happy. You can be intoxicated at your job.
So that allowed me to flourish as a d answer.
There was no restraints. So if I wanted to be
on van x, if I wanted to be on roxy
Hood and that was what he enabled me to support
(11:14):
my habit likely Grace youngest Dougherty Ryan was also having
a tough time. He was living with his mom, getting
in and out of trouble with the law and not
going very far. Here he is speaking with Beth Greenwald again.
My mother always hald like a really strong work ethic
and so like. I think I got my first job
when I was like thirteen years old, fourteen, and then
I always worked and went to school at the same time.
(11:34):
But then I got kicked out of high school. They
didn't give you like a suspension and let you come back, no,
so like, and then I had to go to adulthood
and then I got my g D. And what did
you do after you did the adult education thing? I
funked around a lot. I just sold small amounts of
drugs and hung out. I didn't really have that much ambition,
so I just kind of like a hedonistic streak in me.
(11:56):
And I like to do drugs and I like to
lay on the beach man. I like to go so finn.
I like to drive around. I like to do things
you'd like to do in your nineteam drink too much
and drive to Ryan's brother, Dylan stepped in and help
Brian get back on track. After a while, my brother
told me, if you want, I'll get you a job
over here. And I moved to the Pepford Hills and
hung out with my brother and I got to know
(12:16):
him a lot better, and thembre about five years in
my life I got to spend with my brother, so
I was really grateful for that time. And he taught
me a lot about the counter work on cars. He
told me how to do a lot of things with
my hands because I was raising in a household essentially
with all women, so like missing a lot of man
type of education. And that's the type of ship that
I got a crash course in from him. Ryan was
twenty years old at this point, and not only was
(12:37):
he doing well professionally, but his personal life was in
a really happy place. Well, my baby's mother was pregnant.
I like that whole experience, Like she was never more
beautiful to me than when she was pregnant. She got
big as a goddamn beach ball, and she was the
prettiest I've ever seen their little chubby. Here's Dylan again
talking about Ryan. He just needed an opportunity, That's all
(12:57):
I needed with the opportunity, and I forwarded him the
opportunity to do better. And this call was from the
Federal prison better. And he was doing and he was
doing good. He was doing the right things. He was
going to work, he was being productive. He would have
been taking care of his kid in his with his girlfriend,
and he was in a position to be a part
of his DS life and be a positive influence and
(13:17):
obviously working. On August first eleven, everything changed. Ryan was
set to appear in court for something that happened two
years prior when he was a teenager. Ryan intended on
pleading no contest to two felony charges, the first sending
a minor harmful information, the second lewd and the siviest conduct. However,
(13:37):
when he got to court, the deal he thought he'd
agreed to had changed. He explains the original agreement his
lawyer presented him with. My lawyer promised me. He's like, yo,
when you come to court, you're gonna get probation for something,
and it's gonna be a non sex offendery charge and
you're not gonna have to register. You're gonna have to
do five years of probation. And I'm like, all right, bet,
I'll sign up for that. We're going to take a
(14:03):
quick break here. We'll be back in a moment. Two
years prior to the court appearance, Ryan had sent sexually
explicit text messages back and forth with an underaged girl
he'd never met. He'd stayed out of trouble after that,
but it was now time to face the fallout from
(14:24):
what he'd done. On that day in court August first,
two thousand eleven, Ryan's lawyer informed him there was a
different prosecutor and a completely different deal on the table.
And then I get the court. The son of a
bitch is late. He's like, all the state attorney has changed.
It's not the guy anymore. And the best deal she's
telling the cut with you his twelve years reprovation. And
I'm like, fuck that ship. We'll crank it up and
go to trial. I've already paid your almost twenty racks,
(14:46):
which the majority of my mom, Paige, who could ill
afford it. Ryan's attorney went on to explain what going
to trial would mean for him. It was an impossible choice.
But if you go to trial, they're gonna pull your
bond and put you in jail. Right now, Well, my
son was supposed to be born ten days from there.
I don't want to miss that. Like I don't know.
I'm just bad, bad, bad, bad and worse like shitty option,
(15:06):
worse option, worse option. When Ryan went to court, older
brother Dylan had planned to go with him but didn't.
It's something that haunts Dill into this day. But it
was very odd the whole way that everything got forward
and transpired. I was supposed to go to court with
him that day, and I was busy. Might have been
that things would have happened differently. I would have what
would happening. I probably have told him we'll going to trial,
(15:26):
you know what I mean. But Ryan had to make
the decision on the spot, and he chose probation. I
came from the courthouse immediately to the probation office. He
said I did not need a monitor, and then I
got to the probation office and they were like, you
need one, and I argue with the p O and
he was like, well, we can figure it out down
the road, but fuck you for right now. You'll do
as I say, or I'll violate you right here and now.
(15:46):
And it's like you're excluding me from society to the
point of where how am I supposed to succeed? Ryan
raced home from the meeting with the parole officer to
get to his house. The officer was set to do
a home check shortly after their meeting, and Ryan wanted
to beat him there. So I'm driving my ass off,
and the whole time I'm kind of like paranoid that
they can see how fast I'm going. I'm worried. I
want to get home to get the guns out of
(16:07):
the house before they get there. Dylan was there before
I got home. I just unloaded on him and told me,
first of all, we squared everything with the probation and
ship like that in about court and what happened there,
and I said, Bro, I just can't take it anymore.
I have reached a point where I just can't do it. Bro,
the officer ride to the house right after Ryan did.
Dylan was staying there, as was Ryan's nine months pregnant
(16:30):
girlfriend Amber. Since Ryan was charged with sexually inappropriate texting
with the minor, the probation officer was looking for evidence
of any children in the home, which would be a violation.
The crib and other preparation for the baby to come.
We're everywhere. The probation officers like, hey, when your son
is born, you can't be around him, And I'm like,
what are you talking about. It's gonna be borne in
ten days. This is where she lives, where she's putting
(16:52):
I don't know, but she can't be here. So it's
like an impossible situation all the way around it, Like
what what didn't you expect? What did you think was
going to happen out of that situation that you put
me in. Granted I did, I did what I did,
and I put myself in that situation. It was my
fault that it got to that point. But when I'm
in that point, you're not helping me. You're hurting me.
(17:14):
You're pouring water on me while I'm in the water.
I'm drowning here, and you're like, hey, I have this
cup of water. You look thirsty. In order for Ryan
to meet the requirements of his probation, he had to
provide his home address. It seems like a simple ask,
but it was anything but Dylan helps explain why it
really at all fulled down to the address. I think
in the trial it's known as the yellow House. He
(17:34):
doesn't actually have a street address. It doesn't have a
physical address. And there's doing all these you know, hoops
and loops and why he can't provide this address while
the probation officer knows that he lives here and says, oh,
if he doesn't provide the address and we're gonna fil
him such and such. Ryan was given just forty eight
hours to officially get his home address and to have
two pieces of mail delivered to him stating the address,
(17:55):
and to have that reflected on his driver's license. It
was an impossibility a year's older brother, Dylan. That was
the root cause, because I had the probation officer not said, oh,
we're gonna come back and you know we're gonna I'm
gonna Diviyl like you, and it was just like what
you know what I mean? There was no way to
get an address for the place because the place didn't
in the house didn't have a mail box. The house
was a part of a larger piece of property. In
(18:17):
the house is like on the back corner of it
on another street, and it didn't actually have an address.
The house was just there with Miller's dress. That's why
it's called the yellow house. And of course the neighbor
has an addressed, and the other house and other si
has an address, but for some reason, this house doesn't
have an address. And I know this sounds really weird,
but that is the fact. Ryan was frantic thinking about
what would need to happen to fulfill his probation requirements.
(18:40):
I mean literally, like if the probation officer would have
done what I was asking him for, which was I said, hey, bro,
let me get like one week. Because in Florida to
do anything at the d m V office, you have
to have your air certificate, social Security card, in two
forms of certified mail. You have to have all of
that in order to change anything on your driver's license
or and to do anything in your driver's license in
order to up foot in the d n B. That's
(19:01):
all provable facts, and then the provable facts at the
place that I was living, so I didn't even have
a mailbox. All I have was a post office box.
How long would it take to get a mailbox installed?
How long would it take from them to get two
forms to certify mail to the house. And I think
everything to some extent was heightened again. They put you
on probation instead of putting you in jail for a reason,
(19:21):
but then they made it virtually impossible for you to
hit the conditions of that probation, which means that you
were just going to be sent to jail either way.
Ryan felt completely out of options. In forty eight hours,
the probation officer would be back and Ryan would be
arrested for violating parole. He would go to jail, leaving
his nine months pregnant girlfriend alone to have their baby,
(19:44):
the son he would not be able to live with.
The only thing I ever really like dreamed about that
I really wanted mad would to be a father. And
I'm not that hard to please write like I really
wanted really amazing it, like I wanted are now so,
I wanted it on a nice car. I wanted even
blow and I wanted somebody to be able to share
my life with and to have kids and to teach
(20:05):
them better than I got taught, or to just have
kids to enjoy. It's not experienced to be able to
give one I good to them, to be able to
give something back to other people too. But more than anything,
Ryan wanted to be a father. It was really frustrating
for me to see a situation he was kind of
shoehorned into, you know, pitching hole or whatever you want
(20:25):
to call it. And I didn't say to him, but
I thought of my head, I might do. I be
a man, You'll leave my son like a little video message.
Put all the things that I have that are value
in a bag, walk in the woods and eat a bullet.
Let's stop here for another quick break. We'll be back
at a moment. You know, I didn't know if I
(20:54):
was going to do that or if I was just
gonna make a vicious last stand, because I didn't care
if it was just banging it out. This had this
call was from the federal prison and nowhere to direct it.
You know, that night, Ryan concocted a plan with Dylan
and older sister Lee Grace. Ryan had his ankle monitor
on and thought it might be recording him, so The
(21:15):
three wrote notes back and forth. The plan was for
Ryan to leave the very next morning and drive to Mexico.
Once he crossed the border, he would call for his
girlfriend and baby son so they could all be together
as a family. Dylan and Lee Grace were never going
to let him do it alone. I was just so
upset at the situation. I didn't know what we were
going to do. So when I went to my brother's house,
(21:37):
my idea was, my brother's going to be on the run.
I'm going to be on the run. Not only did
Lee Grace want to support Ryan, but she'd recently hit
rock bottom and had nothing tying her to Florida. I
got hired at my first club June of two thousand,
so by the time two thousand eleven came around, I
had been a d answer for eleven years. I was jeating,
(22:00):
really burn out. I didn't want to do it anymore.
I wanted to settle down. I wanted to have a family.
I wanted to have a good job where I made
lots of money. And I guess I didn't really know
how to put all those points together. Lee Grace had
just broken up with their long term boyfriend, Brendan and
was deep in her addiction. I had broken up with Brendan.
(22:20):
We had a really bad breakup, so that sent me
into a tailspin. And I was basically going from friend
a friend, getting whatever prescription drugs they had, doing them,
and leaving the friend's house with their prescription drugs with
or without their permission. So I had basically burned all
my bridges with a lot of my friends, and I
(22:41):
really didn't have anywhere else to go. And I was
very upset that I wasn't in a good stable relationship,
because relationships are very, very important to me, especially with
a significant other. The fresh breakup with Brendan was amplified
by old wounds Lee. Grace's youngest sister, Aaron, the one
she spent years with couch surfing as a teenager, had
(23:02):
passed away. She died of the same heart disease that
killed their father and the entire family, but especially like Grace,
was left angry and adrift. You know, I've always had
that relationship with Brendan that he has been there for me.
He's seen me through so many things, the death of
my sister Aaron. He's seen me lose jobs, he's seen
(23:22):
me in tears, hysteric, hysterically crying, you know, losing my mind.
And he's always been there. He's always been that type
of house that I can live at, you know, the
guy that will always take you back. So when I
lost that, I just felt like I had nothing and
I just wanted to go on the run. Ryan was
also devastated by the loss of their sister, Aaron. When
(23:43):
my sister died, that was a vicious one because man,
if you want to talk about a completely different person,
that's where it felt like I developed two separate personalities
that gone in my head at any given time. Dylan
understandably had a similar reaction when Aaron passed away, or
was like, I had to destrove at home, but you know,
not guarantee tomorrow, and that's time with your family is important.
It's just not something's gonna last forever. This idea of
(24:06):
family being important above all else is what drove Dylan
to join Ryan and Lee Grace on the planned escape
to Mexico. You know, at the time, it was what
I thought was best and most sound solution, and obviously,
you know things that would do over younger, and maybe
you should have slept on the idea before he had
followed through with it, but you know those are all
maybies and hips and fIF fifth would all be drunk.
(24:27):
So I felt like everything was really snaptic head because
you know what I mean, I'm not gonna lie. I
was frustrated because you know, I brought I was younger,
You did a lot of dumb stuff. I just felt
like he was just unfair from the start. You know,
they were bad decisions made under arrest. And obviously, if
I could go back, I wouldn't change for change a lot,
you know, as far as what happens. But you know,
we can't change the pass, not yet. I think he
(24:49):
was under so much stress that my brother Ryan, he
did not know what to do. You know, he's a
young man. He was under a lot of pressure from
his baby's mother. I do remember that. I so paranoid.
I thought that the ankle bracelet that I had on,
you know, might be able even to pick up audio.
It was just a whirlwind. People like, oh, it's far
it's far off to pay, you know what. I was like, Well,
(25:10):
open to the door and put your foot on the ground.
More on that next time. The Dougherty Gang is executive
produced by Stephanie Lae Ducker and me Courtney Armstrong, along
with Beth Greenwald and Shaun McEwen. Editing and sound design
is by Jeff Twa and additional producing by Chris Graeves
and Jeff Shane. The Docrt Gang is a production of
I Heart Radio and Katie Studios. For more podcasts from
(25:33):
my Heart Radio, visit the iHeart Radio app, Apple Podcasts,
or wherever you listen to your favorite shows.
Welcome to the Docerty Gang, a production of I Heart
Radio and Katie Studios. Docr To Gang is the true
story of three siblings. Twenty nine year oldly Grace, I'm
the oldest. We have a very, very loving family. Our
family is very accepting. If you make a mistake, our
family will shoot you out and they will quickly open
their arms. Twenty six year old Dylan. I wish it
(00:22):
had not happened the way, and I wish I had
never been put in that position. And obviously if I
could go back, I would change a lot in twenty
one year old Ryan. I'm not good at covering my track.
I'm not good at lying. I'm not good at being
a cheater. And I'll even'll wake behind me like a
mile wide. The three went on an eight day fifteen
state Crimes free in two thousand eleven that rocked the country.
(00:44):
They liked the notoriety, They liked the fact that they
were on the Monday, liked that they were getting national attention.
That just played in the hole, you know, Bonnie and Clade.
They went from wielding an eight key forty seven while
trying to outrun police in Florida. The police tried to
pull the sibling Joe the first speeding, but instead officers
say the Doherty's pulled out a gun firing December twenty
(01:06):
shots to robbing a bank in Georgia. What do you
get out of it? You get federal charges, you get
to FBI chasing, and you're gonna get your picture taken
to leading police on a high speed car chase across
Colorado ending in a shower of bullets fifty But that's
(01:26):
not where the story begins ten years, because we're coming
up in ten years and I mean, we've done thirty years.
This is the Dockerty Gang Episode one. We can't change
the past, not yet. I'm Courtney Armstrong, a crime producer
at Katie Studios with Stephanie Ledecker. We've been working with
producer Beth Greenwald and The Dockerty Gang for months now.
(01:49):
The three siblings have agreed to tell their story for
the very first time, each from separate prisons. Lee Grace
Dockerty is at Federal Corrections Institute Aliceville and Alabama. Ryan
is in the United States Penitentiary Tucson in Arizona, and
Dylan is at the Federal Corrections Institute in Bennonsville, South Carolina.
This call was from the federal prison. The last time
(02:10):
I spoke to my dad. I don't know if you
ever talked to anybody on their death bed, or had
anybody that you know asked you to do something while
they're trying I guess, but it's the definitely weighed on me.
You know, it was something that I really later on
took the heart. They didn't say, you know, respect your mom,
or do good in the school, or be nice to
your sisters or anything like that. You told me the
last thing I remember him telling me he was looking
out for your little brother. I don't know if he
(02:32):
knew and was going to be right there soon, but
he thought about four hours after that. That's older brother,
Dylan Dougherty. He was just twelve years old when he
made a promise to his father on his deathbed that
he would take care of his little brother. It would
change the course of Dylan's entire life. Here he is
speaking with Beth Greenwald. Family always seems to be the
most important thing to all of you guys. Is it
(02:53):
because you lost your dad? It was just the way
that you were raised For my dad, you know, family
was everything, and that's definitely where I got those ethos
from from him. You know, family, trump's all. No matter
what happens in your family is always tiring. Do you
think things would have been any different if you're if
your dad hadn't passed That's a big question. But John Daddie,
I think things would be a lot different if my
(03:13):
father had passed away. Their story was covered in the
national media and it made us want to know more.
This man hunt has been going on for more than
a week. Harmed, dangerous, and all in the same family
that led to a twenty mile long chase at speeds
of over a hundred miles an hour. Are they three
goldenhearted siblings willing to risk everything for each other or
were they just looking for notoriety. My brother is going
(03:37):
to be on the run. I'm going to be on
the run. I'm on probation, and I burned all my bridges.
It's a really strange feeling to be untethered. You don't
have anything that means anything to you anymore. You've lost
everything that matters. You can't go self surrendered. That doesn't matter.
You're still gonna get the same amount of time you're
gonna get whether or not you keep going from There,
feature film based on the cross country crime spree set
(04:00):
to be released later this year. Here's the movie's writer, director,
and producer Sean McEwen, who's known the siblings intimately for
eight years. The Doctor He's grew up in a small
house in La Couchee, Florida, located about fifty miles outside
of Disney. Mom Barbara was a nurse, and dad known
as Doc, worked in construction. And five kids in seven years, Lee, Grace, Dylan, Devon,
(04:21):
Aaron and Ryan growing up. The key lesson they instilled
on their kids with family first and loyalty is everything.
Youngest Dockery, Ryan talks about their mother. My mom went
crabbing and fishing with me. My mom took me places,
my mom did ship with me. My mom careen love
for me. My mom tried real hard, but we were
just really willful kids, like I'm gonna do what I want.
(04:43):
My mom was always a worker in the family, like
my father did construction and demolition and stuff. But honestly,
I think that my mom's payout class tis and my
father was able to kind of be like more of
a stay at home father with us kids, which was
a blessom. Here's oldest sister Lee Grace. Kids. We were
not the best of children. We are really bad. We
saw you know, we had behavior problems in school. If
(05:03):
we did get in trouble, you know, sometimes even my
dad would laugh at off. So we were raised strict,
but not maybe as strict as other kids. Ryan's always
been the baby of the family. You know, when you
grow up as the youngest child. Me and Ryan have
seven years age difference. He was the type of kid
that everybody just gravitated toward him. He was like the
golden child in our family. He was easy to love
(05:26):
and he was just so easy going. If we laughed
at a joke, he laughed. He just wanted to be
like the big kids. You know. We could be hungry,
We could be spending our last ninety nine on a
Hamburger and he would split it with me. Everything with
Ryan is fifty fifty. He wants to be able to
share things. He's so generous. Dylan was not afraid of anything.
(05:48):
He was always there to protect us, even at a
young age. I always looked at Dylan like he had
this like hero complex. He always wanted to save somebody,
even as we were adults. It was always like I
knew I could do whatever I wanted because I knew
that John was there to protect me. You know, I
could say whatever I wanted, I could fight with anybody,
and my brother was always going to back me up.
(06:09):
You know. It was like my my protector. Even though
he's two years younger than me, I looked at him
as my equal. Here's Dylan. When he was a child,
his father wanted the best for him and felt he'd
have a few more opportunities living with his aunt and
uncle while still staying close to his siblings. Dylan was
legally adopted by his aunt and uncle, who he refers
to as stepmom and stepdad. I would say definitely a
good older brother. I just imparted all of the called
(06:32):
the wisdom that I received from our father and from
my stepdad and even my grandfather. My mom had five
kids in seven years, so there's not a whole lot
of space in between her, so we were all relatively
close to the same age. I think I was kind
of cool growing up. We're all kind of at the
same point in life together. So while the Doctuli's had
fun and leaned on each other during their childhood, things
(06:52):
were tough there wasn't a lot of money, and things
got even tough when once dad died. The siblings were young, Lee,
Grace was bull you dealing with s twelves, and Ryan
just seven years old, So it was hard on the
kids and possibly even harder on mom. The death of
father William Dockerty known as Doc, was tough on everyone,
especially mom Barbara. She was left with five kids to
(07:14):
raise on her own. So my dad was very young,
he was only forty one years old. My mom was
left with all of us kids. Everything fell to my mom,
all the discipline, all the finances, and it was very
difficult for her, you know, because my dad was the
love of her life, her soul mate, so she was
going through losing her love and then also the father
of her children. And that made it really, really difficult
(07:37):
because my mom really had nobody to turn to. Her
family was very distant with her, so they weren't with
my mom's you know, nobody had my mom's back at
that point. She was by herself. She did everything on
her own. She always said the same thing, your father
is my best friend. I cannot live without him. So
I think that was a point where my mom realized
(08:01):
the person that she loved most of the world had
passed away, and I think it really really affected her,
you know, I think even more than she than she
put out there, because she was just struggling. He had
nobody to turn to. At this point, everyone was doing
the best they could. Older brother, Dylan, the one adopted
by his aunt and uncle, had his sight set high
and was on the straightened arrow. When I went to
(08:22):
ninth grade, my mom started home school met uh did
homeschooling for about a year and then enrolled in the
community college. And I went to school for a few semesters,
and then I just thought it did death really wasn't
what I wanted to do. I started working young don't
drive into construction and started making money and doing a
grown man's job when I was sixteen. And I was
making a grown man's paycheck at sixteen and was living
(08:43):
at my parents house, so I had funny of money
to spend. Lee Grace was living a rougher life, CouchSurfing
at various friends places, often with her younger sister Aaron.
We were like gypsies. We were from here to here
to here. You know, we moved so much. I probably
lived in about twenty different places, so there wasn't really
one address that I was using. I was just kind
of going, you know, by the seat of my pamp
(09:06):
and my sister would be there with me. Aaron and
I were going from family friends to our boyfriend's apartments.
We were fourteen and fifteen, so that was a direct
result of my dad's coffee. It was right after a
dad died when Lee Grace went off on her own
with her sister. Things were tough at home. Her relationship
(09:26):
with Mama's volatile, and the only way Lee Grace could
deal with grief and guilt was to get out of
the house. I wasn't dealing with my dad's death very well.
She wasn't holding up her end of the bargain, and
I always I felt so much blame and so much
guilt for my dad dying because I was the oldest child,
and heart attacks are paused by stress, and you kids
stressed your dad out, and now he's dead, and what
(09:48):
are we gonna do. We don't have any money. Dad
didn't leave a will, we didn't have life insurance, so
it was like, you know, you're fourteen years old, You're
worried about getting your drawer's license, and going to up
dances and problems, and now I got to worry about
biblings and my mom. This chaotic living situation Ledley Grace
to drugs, stripping, and never holding down jobs for long.
I never was able to stay in the same position
(10:10):
for any amount of time, because when you're in that
phase of your addiction, it's very hard to get up
in the morning. You're not cooked, you're working when you're hungover,
or you're coming off a bad high, or you're coming
off a binder. So basically I had explained my situation
to some of the people that I work with, and
they basically said, we understand, thank you for telling us,
but you need to go home and come back in
(10:32):
a year when you've got your mind right. And instead
of taking that advice, I basically quit the job. Leaving
the traditional nine to five world would impactly Grace for
years to come, enabling her drug habit and driving her
deeper into addiction. And I went right back to dancing
because they don't care. You know, you come in at
six o'clock at night, seven o'clock at night to start
(10:53):
your shifts. They're not expecting you to take a drug test,
you know, they don't care a futurine Jewish pokes. You know,
you could do whatever you want as long as you're
making me quients happy. You can be intoxicated at your job.
So that allowed me to flourish as a d answer.
There was no restraints. So if I wanted to be
on van x, if I wanted to be on roxy
Hood and that was what he enabled me to support
(11:14):
my habit likely Grace youngest Dougherty Ryan was also having
a tough time. He was living with his mom, getting
in and out of trouble with the law and not
going very far. Here he is speaking with Beth Greenwald again.
My mother always hald like a really strong work ethic
and so like. I think I got my first job
when I was like thirteen years old, fourteen, and then
I always worked and went to school at the same time.
(11:34):
But then I got kicked out of high school. They
didn't give you like a suspension and let you come back, no,
so like, and then I had to go to adulthood
and then I got my g D. And what did
you do after you did the adult education thing? I
funked around a lot. I just sold small amounts of
drugs and hung out. I didn't really have that much ambition,
so I just kind of like a hedonistic streak in me.
(11:56):
And I like to do drugs and I like to
lay on the beach man. I like to go so finn.
I like to drive around. I like to do things
you'd like to do in your nineteam drink too much
and drive to Ryan's brother, Dylan stepped in and help
Brian get back on track. After a while, my brother
told me, if you want, I'll get you a job
over here. And I moved to the Pepford Hills and
hung out with my brother and I got to know
(12:16):
him a lot better, and thembre about five years in
my life I got to spend with my brother, so
I was really grateful for that time. And he taught
me a lot about the counter work on cars. He
told me how to do a lot of things with
my hands because I was raising in a household essentially
with all women, so like missing a lot of man
type of education. And that's the type of ship that
I got a crash course in from him. Ryan was
twenty years old at this point, and not only was
(12:37):
he doing well professionally, but his personal life was in
a really happy place. Well, my baby's mother was pregnant.
I like that whole experience, Like she was never more
beautiful to me than when she was pregnant. She got
big as a goddamn beach ball, and she was the
prettiest I've ever seen their little chubby. Here's Dylan again
talking about Ryan. He just needed an opportunity, That's all
(12:57):
I needed with the opportunity, and I forwarded him the
opportunity to do better. And this call was from the
Federal prison better. And he was doing and he was
doing good. He was doing the right things. He was
going to work, he was being productive. He would have
been taking care of his kid in his with his girlfriend,
and he was in a position to be a part
of his DS life and be a positive influence and
(13:17):
obviously working. On August first eleven, everything changed. Ryan was
set to appear in court for something that happened two
years prior when he was a teenager. Ryan intended on
pleading no contest to two felony charges, the first sending
a minor harmful information, the second lewd and the siviest conduct. However,
(13:37):
when he got to court, the deal he thought he'd
agreed to had changed. He explains the original agreement his
lawyer presented him with. My lawyer promised me. He's like, yo,
when you come to court, you're gonna get probation for something,
and it's gonna be a non sex offendery charge and
you're not gonna have to register. You're gonna have to
do five years of probation. And I'm like, all right, bet,
I'll sign up for that. We're going to take a
(14:03):
quick break here. We'll be back in a moment. Two
years prior to the court appearance, Ryan had sent sexually
explicit text messages back and forth with an underaged girl
he'd never met. He'd stayed out of trouble after that,
but it was now time to face the fallout from
(14:24):
what he'd done. On that day in court August first,
two thousand eleven, Ryan's lawyer informed him there was a
different prosecutor and a completely different deal on the table.
And then I get the court. The son of a
bitch is late. He's like, all the state attorney has changed.
It's not the guy anymore. And the best deal she's
telling the cut with you his twelve years reprovation. And
I'm like, fuck that ship. We'll crank it up and
go to trial. I've already paid your almost twenty racks,
(14:46):
which the majority of my mom, Paige, who could ill
afford it. Ryan's attorney went on to explain what going
to trial would mean for him. It was an impossible choice.
But if you go to trial, they're gonna pull your
bond and put you in jail. Right now, Well, my
son was supposed to be born ten days from there.
I don't want to miss that. Like I don't know.
I'm just bad, bad, bad, bad and worse like shitty option,
(15:06):
worse option, worse option. When Ryan went to court, older
brother Dylan had planned to go with him but didn't.
It's something that haunts Dill into this day. But it
was very odd the whole way that everything got forward
and transpired. I was supposed to go to court with
him that day, and I was busy. Might have been
that things would have happened differently. I would have what
would happening. I probably have told him we'll going to trial,
(15:26):
you know what I mean. But Ryan had to make
the decision on the spot, and he chose probation. I
came from the courthouse immediately to the probation office. He
said I did not need a monitor, and then I
got to the probation office and they were like, you
need one, and I argue with the p O and
he was like, well, we can figure it out down
the road, but fuck you for right now. You'll do
as I say, or I'll violate you right here and now.
(15:46):
And it's like you're excluding me from society to the
point of where how am I supposed to succeed? Ryan
raced home from the meeting with the parole officer to
get to his house. The officer was set to do
a home check shortly after their meeting, and Ryan wanted
to beat him there. So I'm driving my ass off,
and the whole time I'm kind of like paranoid that
they can see how fast I'm going. I'm worried. I
want to get home to get the guns out of
(16:07):
the house before they get there. Dylan was there before
I got home. I just unloaded on him and told me,
first of all, we squared everything with the probation and
ship like that in about court and what happened there,
and I said, Bro, I just can't take it anymore.
I have reached a point where I just can't do it. Bro,
the officer ride to the house right after Ryan did.
Dylan was staying there, as was Ryan's nine months pregnant
(16:30):
girlfriend Amber. Since Ryan was charged with sexually inappropriate texting
with the minor, the probation officer was looking for evidence
of any children in the home, which would be a violation.
The crib and other preparation for the baby to come.
We're everywhere. The probation officers like, hey, when your son
is born, you can't be around him, And I'm like,
what are you talking about. It's gonna be borne in
ten days. This is where she lives, where she's putting
(16:52):
I don't know, but she can't be here. So it's
like an impossible situation all the way around it, Like
what what didn't you expect? What did you think was
going to happen out of that situation that you put
me in. Granted I did, I did what I did,
and I put myself in that situation. It was my
fault that it got to that point. But when I'm
in that point, you're not helping me. You're hurting me.
(17:14):
You're pouring water on me while I'm in the water.
I'm drowning here, and you're like, hey, I have this
cup of water. You look thirsty. In order for Ryan
to meet the requirements of his probation, he had to
provide his home address. It seems like a simple ask,
but it was anything but Dylan helps explain why it
really at all fulled down to the address. I think
in the trial it's known as the yellow House. He
(17:34):
doesn't actually have a street address. It doesn't have a
physical address. And there's doing all these you know, hoops
and loops and why he can't provide this address while
the probation officer knows that he lives here and says, oh,
if he doesn't provide the address and we're gonna fil
him such and such. Ryan was given just forty eight
hours to officially get his home address and to have
two pieces of mail delivered to him stating the address,
(17:55):
and to have that reflected on his driver's license. It
was an impossibility a year's older brother, Dylan. That was
the root cause, because I had the probation officer not said, oh,
we're gonna come back and you know we're gonna I'm
gonna Diviyl like you, and it was just like what
you know what I mean? There was no way to
get an address for the place because the place didn't
in the house didn't have a mail box. The house
was a part of a larger piece of property. In
(18:17):
the house is like on the back corner of it
on another street, and it didn't actually have an address.
The house was just there with Miller's dress. That's why
it's called the yellow house. And of course the neighbor
has an addressed, and the other house and other si
has an address, but for some reason, this house doesn't
have an address. And I know this sounds really weird,
but that is the fact. Ryan was frantic thinking about
what would need to happen to fulfill his probation requirements.
(18:40):
I mean literally, like if the probation officer would have
done what I was asking him for, which was I said, hey, bro,
let me get like one week. Because in Florida to
do anything at the d m V office, you have
to have your air certificate, social Security card, in two
forms of certified mail. You have to have all of
that in order to change anything on your driver's license
or and to do anything in your driver's license in
order to up foot in the d n B. That's
(19:01):
all provable facts, and then the provable facts at the
place that I was living, so I didn't even have
a mailbox. All I have was a post office box.
How long would it take to get a mailbox installed?
How long would it take from them to get two
forms to certify mail to the house. And I think
everything to some extent was heightened again. They put you
on probation instead of putting you in jail for a reason,
(19:21):
but then they made it virtually impossible for you to
hit the conditions of that probation, which means that you
were just going to be sent to jail either way.
Ryan felt completely out of options. In forty eight hours,
the probation officer would be back and Ryan would be
arrested for violating parole. He would go to jail, leaving
his nine months pregnant girlfriend alone to have their baby,
(19:44):
the son he would not be able to live with.
The only thing I ever really like dreamed about that
I really wanted mad would to be a father. And
I'm not that hard to please write like I really
wanted really amazing it, like I wanted are now so,
I wanted it on a nice car. I wanted even
blow and I wanted somebody to be able to share
my life with and to have kids and to teach
(20:05):
them better than I got taught, or to just have
kids to enjoy. It's not experienced to be able to
give one I good to them, to be able to
give something back to other people too. But more than anything,
Ryan wanted to be a father. It was really frustrating
for me to see a situation he was kind of
shoehorned into, you know, pitching hole or whatever you want
(20:25):
to call it. And I didn't say to him, but
I thought of my head, I might do. I be
a man, You'll leave my son like a little video message.
Put all the things that I have that are value
in a bag, walk in the woods and eat a bullet.
Let's stop here for another quick break. We'll be back
at a moment. You know, I didn't know if I
(20:54):
was going to do that or if I was just
gonna make a vicious last stand, because I didn't care
if it was just banging it out. This had this
call was from the federal prison and nowhere to direct it.
You know, that night, Ryan concocted a plan with Dylan
and older sister Lee Grace. Ryan had his ankle monitor
on and thought it might be recording him, so The
(21:15):
three wrote notes back and forth. The plan was for
Ryan to leave the very next morning and drive to Mexico.
Once he crossed the border, he would call for his
girlfriend and baby son so they could all be together
as a family. Dylan and Lee Grace were never going
to let him do it alone. I was just so
upset at the situation. I didn't know what we were
going to do. So when I went to my brother's house,
(21:37):
my idea was, my brother's going to be on the run.
I'm going to be on the run. Not only did
Lee Grace want to support Ryan, but she'd recently hit
rock bottom and had nothing tying her to Florida. I
got hired at my first club June of two thousand,
so by the time two thousand eleven came around, I
had been a d answer for eleven years. I was jeating,
(22:00):
really burn out. I didn't want to do it anymore.
I wanted to settle down. I wanted to have a family.
I wanted to have a good job where I made
lots of money. And I guess I didn't really know
how to put all those points together. Lee Grace had
just broken up with their long term boyfriend, Brendan and
was deep in her addiction. I had broken up with Brendan.
(22:20):
We had a really bad breakup, so that sent me
into a tailspin. And I was basically going from friend
a friend, getting whatever prescription drugs they had, doing them,
and leaving the friend's house with their prescription drugs with
or without their permission. So I had basically burned all
my bridges with a lot of my friends, and I
(22:41):
really didn't have anywhere else to go. And I was
very upset that I wasn't in a good stable relationship,
because relationships are very, very important to me, especially with
a significant other. The fresh breakup with Brendan was amplified
by old wounds Lee. Grace's youngest sister, Aaron, the one
she spent years with couch surfing as a teenager, had
(23:02):
passed away. She died of the same heart disease that
killed their father and the entire family, but especially like Grace,
was left angry and adrift. You know, I've always had
that relationship with Brendan that he has been there for me.
He's seen me through so many things, the death of
my sister Aaron. He's seen me lose jobs, he's seen
(23:22):
me in tears, hysteric, hysterically crying, you know, losing my mind.
And he's always been there. He's always been that type
of house that I can live at, you know, the
guy that will always take you back. So when I
lost that, I just felt like I had nothing and
I just wanted to go on the run. Ryan was
also devastated by the loss of their sister, Aaron. When
(23:43):
my sister died, that was a vicious one because man,
if you want to talk about a completely different person,
that's where it felt like I developed two separate personalities
that gone in my head at any given time. Dylan
understandably had a similar reaction when Aaron passed away, or
was like, I had to destrove at home, but you know,
not guarantee tomorrow, and that's time with your family is important.
It's just not something's gonna last forever. This idea of
(24:06):
family being important above all else is what drove Dylan
to join Ryan and Lee Grace on the planned escape
to Mexico. You know, at the time, it was what
I thought was best and most sound solution, and obviously,
you know things that would do over younger, and maybe
you should have slept on the idea before he had
followed through with it, but you know those are all
maybies and hips and fIF fifth would all be drunk.
(24:27):
So I felt like everything was really snaptic head because
you know what I mean, I'm not gonna lie. I
was frustrated because you know, I brought I was younger,
You did a lot of dumb stuff. I just felt
like he was just unfair from the start. You know,
they were bad decisions made under arrest. And obviously, if
I could go back, I wouldn't change for change a lot,
you know, as far as what happens. But you know,
we can't change the pass, not yet. I think he
(24:49):
was under so much stress that my brother Ryan, he
did not know what to do. You know, he's a
young man. He was under a lot of pressure from
his baby's mother. I do remember that. I so paranoid.
I thought that the ankle bracelet that I had on,
you know, might be able even to pick up audio.
It was just a whirlwind. People like, oh, it's far
it's far off to pay, you know what. I was like, Well,
(25:10):
open to the door and put your foot on the ground.
More on that next time. The Dougherty Gang is executive
produced by Stephanie Lae Ducker and me Courtney Armstrong, along
with Beth Greenwald and Shaun McEwen. Editing and sound design
is by Jeff Twa and additional producing by Chris Graeves
and Jeff Shane. The Docrt Gang is a production of
I Heart Radio and Katie Studios. For more podcasts from
(25:33):
my Heart Radio, visit the iHeart Radio app, Apple Podcasts,
or wherever you listen to your favorite shows.
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