Prime and Only Suspect Part 2: The Unsolved Disappearance of Kip Hess, Keith Fleming, and Charles Collingwood

Episode Transcript
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Speaker 2 (00:10):
Hi everyone.

Speaker 1 (00:11):
If you haven't listened to part one of this episode,
stop what you're doing and go do that now, or
this episode won't make a lot of sense. As a
brief refresher of where we left off, I introduced the
story of Kip Hass's disappearance last episode, a twelve year
old Merit Island, Florida boy who never made it to
school one day after setting off on his bike.

Speaker 2 (00:34):
Kip was a local boy scout who.

Speaker 1 (00:36):
Had been befriended by a man named John Rodney McRae.
Mcray was working security at a local church fair and
Kip was there volunteering with his boy scout troope. Little
did Kip know he was talking to a sexual predator
who had murdered a little boy decades earlier. In Part one,

(00:56):
I go into the details of eight year old Joey
Housey's a due and murder in Michigan in nineteen fifty,
as well as McRae's confession, trial and sentencing. However, a
Supreme Court decision about life without the possibility of parole
for juvenile offenders changed everything, and McRae was once again

(01:16):
free to rebuild a life. In the early nineteen seventies,
that would come at an enormous cost. I'm your host, Megan,
and each week on a Simpler Time True Crime, I
cover older unsolved cases and challenge the idea that a
simpler time means a safer time. This week, I'm bringing
to you part two of the unsolved disappearances of Kip Hess,

(01:41):
Charles Collingwood, and Keith Fleming. After getting out of prison,

(02:05):
Mcray settled down and married a woman named Barbara, and
in nineteen seventy four she gave birth to their son, Martin.
In late nineteen seventy five, mcray was allowed to leave
Michigan after his parole had ended, and he moved his
family to the Miami area of Florida, where he entered
the prison system as a guard. In nineteen seventy six,

(02:27):
he landed a more permanent job in Brevard County at
the now defunct Brevard Correctional Institution, which was a facility
that housed adolescent male offenders. There was no official background check,
and nineteen seventy six had its limitations. It's not like
how today you can fingerprint people and run full digital

(02:48):
background checks. Mcray lied on his application and did not
disclose his own criminal history. And the facility didn't second
check it. At least that's what most of the narratives
are said. There was one that said he was participating
in some sort of re entry type of employment program,
but I only saw that once and I couldn't confirm it,

(03:10):
whereas just about every other source talked about him lying.
McRae excelled in the job and he was promoted to
a leadership role in the facility, but beneath the facade,
his darkness still lurked. He increasingly spent time along the
Florida coast, especially at a pier near Coco Beach where
young boys like to surf. There he'd make conversation with

(03:33):
them and begin his grooming process, and this very well
could have set up the space for him to meet
a young teen boy named Keith Fleming. Keith was thirteen
years old in April of nineteen seventy seven, and he
had a surfer boy look to him. He had white, blonde,
shoulder length hair, and an accident had knocked out his
front teeth, and he had specialized work done in implantations,

(03:58):
which were apparently very well done, and it was hard
to even notice until you got close to him. Nevertheless,
possibly because he was kind of self conscious. All photos
out there of Keith have either kind of a serious,
stoic face or a closed mouth smirk for his smile.
On the afternoon of April twenty eighth, nineteen seventy seven,

(04:19):
Keith's parents dropped him off at his girlfriend's residence in
Coco Beach after school. He needed to be home around dinnertime,
and he was supposed to meet back at the house
where his older brother would be and they would ride
in the family vehicle to pick his mom up from
work at a local restaurant. After visiting his girlfriend, he
rode with her up on her bike to a busy

(04:40):
intersection and then hopped off. From there, he said he'd hitchhike,
something very common both in the nineteen seventies and in
Cocoa Beach specifically. When his girlfriend got back to her
home minutes later, she told her mom that Keith had
planned a hitchhike, and even though it was normal at
that time, his girlfriend's mother said, Oh, don't have him hitchhike,

(05:03):
that's dangerous. I'll give him ride home. So they hopped
back in the girlfriend's mother's car and they were back
to that intersection in just a minute, but in that
time he was already gone. The mother was disappointed, but
figured he probably was able to just thumber ride pretty
quick and that it probably was okay.

Speaker 2 (05:23):
But it wasn't.

Speaker 1 (05:25):
Keith's brother waited for him and he never showed up.
When he arrived to the restaurant to pick up his
mother and told her that Keith never came home, his
mother knew right away something had happened. Keith wasn't a
perfect angel, but he always had communicated with his mother,
and he'd never run away like this, much like with Kip.
Authorities believed Keith ran away. He had been hitchhiking after all,

(05:49):
and had been in a little bit of trouble recently,
nothing major, but his mom had caught him with some
marijuana and his grades had slipped a little bit. The
Flemings Fell felt that Keith had met with foul play,
but after interviewing his friends and finding no motive, Keith
was labeled as a juvenile run away by police. One

(06:09):
complication with that, especially in the nineteen seventies, was that
kids would be in the system with a bolo for them,
but once they turned eighteen, their case would either be
reclassified or purged. Knowing all of that, the Flemings didn't
wait around for police to take Keith's disappearance seriously. They
put up flyers in area shops and conducted their own investigations,

(06:33):
and early on his mother had her own idea about
a possibility. When Keith would be in the car with
his mother on a one to a in Cocoa Beach,
the same stretch of highway Keith hitchhiked on the day
he went missing, they'd often see women on the concrete
median handing out carnation flowers. His mother would say who

(06:54):
are they, and he'd say, Oh, those are just some
friends of mine. In nineteen seventy, Cocoa Beach gave way
to Sun Young Moon's Unification Church, and what Missus Fleming
would often call the Flower Girls were better known as
the Moonies. The Moonies are widely considered a cult, and
they held a lot of controversy centered largely on their

(07:17):
recruitment tactics, internal control, and political influence. During the nineteen
seventies and eighties, the group was widely accused of high pressure,
deceptive recruitment, often targeting vulnerable youth adults, isolating them from
family and moving them quickly into communal living and NonStop fundraising.
Former members who got out and experts described the organization

(07:41):
as using sleep deprivation, intense group bonding, and strict obedience
to leadership to maintain control, which led to the widespread
label of a cult. The church's practice of mass arranged weddings,
where thousands of couples were matched by Moon himself, also
drew public concern and media attention. Financial controversies emerged as well,

(08:05):
particularly around their aggressive fundraising practices, their hidden business interests,
and accusations that members were pressured to turn over their income.
Another layer of controversy involved the movements political activity, and
that's a whole rabbit hole in and of itself, but
all combined, these elements made the Moonies one of the

(08:26):
most scrutinized and debated religious movements of the late twentieth century.
Missus Fleming believed that Keith had possibly been recruited into
the Moonies and wasn't able to contact her, and this
was coupled by troubling phone calls.

Speaker 2 (08:41):
She received three years after.

Speaker 1 (08:42):
Keith's disappearance in nineteen eighty. There were three calls total.
She told Florida Today quote. I got a phone call
one day last spring, and I heard this voice on
the other end. It sounded like there was something else
going on in the background, but it said I just
want to talk to my mom, and then they hung up,

(09:03):
and you know, right away, I say it's him, It's Keith.

Speaker 2 (09:07):
I know that voice. I could swear it was him.

Speaker 1 (09:10):
She went on to say that later, the second abrupt
message just said I love you, and then there was
a disconnection and finally the last call helped me and
the line went dead. Keith's mother was convinced that it
was her son, but his dad was skeptical and thought
it was maybe some sort of prank. The FBI commented

(09:32):
specifically on the Moone's and kidnapping. The FBI stated that
the Moonies were problematic for sure, but they weren't known
for kidnapping, and they had no indication that Keith was kidnapped.
But missus Fleming wondered if he truly had gone willingly
or been coerced into going, and then he got sucked
into this cult and was unable to leave. My heart
broke when I read the quote, she told Florida Today.

(09:56):
She said, I don't understand it. If he was a
bad boy and he did bad things, they'd find him.
If you're wanted criminal, they'd track you down. No one's
even looking for him. Years went by, and it took
a while before McRae was considered potentially involved in Keith's case,
especially later on when he would tell investigators that he

(10:19):
liked to hang out at the Cocoa Beach Pier and
he liked to watch the teen boys there. Had he
made enough contact and built trust with Keith and just
happened upon him that day.

Speaker 2 (10:29):
When he was hitchhiking.

Speaker 1 (10:31):
Keith's mom would say decades later that sometimes she would
just expect him to walk in the door and say, hey,
I'm here, mom, I have a family, here's my kids,
and I'm home now. But that day never came. As
you look at Keith's case in real time and slow
down the clock, his case had fallen a bit into
the background of other boys considered runaways in nineteen seventy

(10:56):
eight and into nineteen seventy nine, and in nineteen seventy
nine that's when kipling Hest disappeared, and then later at
the end of nineteen seventy nine, another person would go missing.

(11:20):
Charles Collingwood was twenty years old and housed at the
Brevard Correctional facility that McRae worked at. He was there
for automobile theft and was near the end of a
four year sentence. On December twelfth, nineteen seventy nine, he
was doing outdoor landscaping work under minimum supervision due to
his history of good behavior. He allegedly told the guard

(11:44):
that he needed to use the bathroom and by that,
I mean take a leak in the woods. Picture that,
and as he got over towards the woods, he took
off running. The guard was unable to chase after him
because he'd risk leaving the rest of the prisoners unsupervised.
It seemed something was up from the get go, because
even in early reporting, the idea that Collingwood was helped

(12:07):
to escape by a friend came up. The more the
investigation turned inward in the prison, the more investigators searching
for the escaped inmate heard rumors from informants, rumors that
Charles Collingwood had been sexually involved with John Rodney mcray.
And I want to be careful with my language here because,

(12:27):
in my opinion, when there is a power dynamic at
play like this, where there is a prisoner and a
prison guard or someone in authority is involved, there is
no space for true consent. Furthermore, several informants stated that
Collingwood had begun blackmailing mcray about the sexual activity and
threatening to expose him. When mcray was questioned about this,

(12:52):
he denied it and said that Collingwood was an informant
to him and kept him in the loop of other
prisoners' activities. Authorities weren't buying it and dug into mcray's history,
finding out about his nineteen fifty murder of Joey Howsey,
and then they started to wonder what other cases of
boys in Florida McRae might have been involved in. Feeling

(13:16):
the heat, Mcray, his wife, and his son all left
Florida in the middle of the night one evening and
moved back to Michigan. He never even put in his
official resignation or cleaned out his worklocker and authorities would
take care of that for him.

Speaker 2 (13:33):
And what did they find?

Speaker 1 (13:35):
A missing person's flyer for kipling Hess. Authorities in Florida
now believed that mcray helped Collingwood get out of prison
and then killed him on the outside to.

Speaker 2 (13:46):
Keep him quiet.

Speaker 1 (13:48):
They also believed he was involved in other disappearances, such
as that of Keith Fleming and or Kip Hess, but
suspicions don't equal convictions, and they lacked evidence to bring
forth charges in any of the cases. As McRae got
back to Michigan, he purchased a plot of land and

(14:08):
a trailer, and he had a bit of a hobby farm.
His son, Martin was in elementary school going into middle
school at this point, and he had adolescent friends. Mcray
got involved in the traveling Carnival and four Aage clubs.
Because of his carnival travel to places like Arizona, Oklahoma,
and California, police believe he may be responsible for more

(14:31):
crimes that have a similar mo that he hasn't been
connected to. If you're a listener in these states and
recall a nineteen eighty's abduction or missing person's case of
a teen boy that seems similar to these, it might
be worth submitting a tip around McRae. Chillingly, he would
teach boy scouts about raising goats and even do field

(14:53):
trips with kids and taking a page out of Gaysey's playbook,
mcray would also often dress as a client. In mid
September nineteen eighty seven, a fifteen year old boy named
Randy Laffer would go missing on the way to his
friend's house after school in Claire County, Michigan, or at
least that's what they thought. Randy packed enough clothes to

(15:16):
be gone for two nights, but he never arrived home,
and he apparently never arrived there, to which his friend said,
I was never expecting him. Investigators in Claire County examined
the runaway theory, just as investigators in Florida had with
their missing boys, especially because it seemed that Randy had

(15:38):
fed his parents a story even though he had no
history of running away. Initially, they thought maybe he was
staying with a friend or someone that they just didn't
approve of, and so that's why he had lied about going.

Speaker 2 (15:50):
To the other friend's house.

Speaker 1 (15:52):
More so than with the other cases in Florida, though
investigators in Michigan were quicker to believe that foul play
might be involved. Still, search parties set out and guess
who was eager to join, none other than mcray himself,
Just as he had done in the other cases. Investigators

(16:13):
had a gut instinct about foul play, which was only
strengthened by a call from authorities in Florida. They hadn't
given up on the cases of Charles and Kip in particular,
and they found out where mcray had relocated to. They
wanted authorities up there in Michigan to know that McRae

(16:34):
was a prime suspect in cases down there, and that
he presented danger to the children of their community in Michigan.
The hairs on the back of investigators next stood up
because Martin McRae was friends with Randy Laffer, and the
Laffers in mcray's were nearby neighbors to one another, so

(16:55):
authorities in Michigan paid mcray a visit. Mcray denied any involvement, and,
just like he had with the pressure he felt in Florida,
he booked it out of town with his family and
relocated all the way across the country to Mesa, Arizona.
He even left his dog behind, tied to a tree

(17:15):
with a note to the neighbor asking him to take
care of it. Randy's case would join kIPS, Keith's and
Charles as a cold case, and it would stay that
way for ten years.

Speaker 2 (17:28):
But that would all change. In August of.

Speaker 1 (17:30):
Nineteen ninety seven, a hired hand on the property formerly
owned by McRae was digging a hole in the ground
to get rid of junk found on mcray's property when
they found something horrible, the skeletal remains of a young boy.
Dental records identified the remains as Randy Lawfer, and a

(17:53):
forensic exam showed he had been repeatedly stabbed in the
neck lower back in Pelvi, and evidence on the bone
suggested he had been bound, possibly gagged, and tortured before
his death. Authorities got a warrant and began digging all
over the property looking for more remains. The Hess family

(18:15):
and others looked to see if their boys remains would
be found. They waited with anxious anticipation, but that never happened.
Police were finally closing in on mcray, but so many
boys had to suffer before he faced real consequences. In
nineteen ninety seven, mcray and his son, Martin, who was

(18:37):
now twenty three years old, were arrested in Mesa, Arizona,
for Randy's murder. McRae was charged with first Dregrea murder
and Martin was arrested for being in accessory to the crime,
as it was believed that he had helped bury Randy's body.
Those charges against Martin were dropped because at the end
of the day, Martin would have only been thirteen years

(19:00):
old in nineteen eighty seven and under the control and
influence of his father. It seems that police were trying
to leverage mcgray's son to try to get mcray to
come clean about what happened with Randy as well as
the other killings. But he didn't really have a soul
and he wouldn't budge. In fact, at times he'd laugh
about the Florida cases and taunt if you don't have

(19:22):
a body, you don't have me. Mcgray's trial opened in
September of nineteen ninety eight, but prosecutors faced a major hurdle.
There was nothing forensic that tied him to Randy Lawfer's death.
To bridge that gap, they reached back to the early
Housey case and drew a line between the two. The patterns,

(19:43):
they argued, were far too similar to ignore. In each case.
Mcray was the last person known to be with the boy.
He inserted himself into the search as if he were helping,
and both victims were found with multiple sharp force injuries,
buried and secluded sp spots not far from mcray's own home.

Speaker 2 (20:03):
It worked. Mcray was charged with first degree murder.

Speaker 1 (20:07):
And now in his sixties, was sentenced.

Speaker 2 (20:09):
To life in prison.

Speaker 1 (20:11):
But it's never that easy with mcray as it He
appealed as verdict on the basis of having ineffective counsel,
and that was granted. While that all played out, just
as a side note, his son Martin was arrested in
Nevada for molesting his own daughter and her friends. Apparently,
Martin had gone camping with some of his kids and

(20:33):
their friends and become stranded when his truck broke down
in the wilderness. They spent a night in the mountains,
and after getting help, the next day children went to
their parents to say that Martin McRae had molested them.
He was sentenced to ten years to life in prison.
That made things interesting because Martin was hoping to be
able to give information he knew about the cases to

(20:56):
help his own case as the fate of his dad's
trial hung in the balance. And interestingly enough, John Rodney
mcray's wife had already told authorities that her husband had
committed the Collingwood and Hess murders, but her testimony wasn't
admissible in court. McRae was granted a new trial in

(21:17):
two thousand and four after his initial conviction was thrown out.
He was tried again in two thousand and five and
found guilty of first gree murder. He was sentenced to
life in prison without the possibility of parole, With his
fate sealed. Local newspaper reporters stated that mcray was considering
coming forward with information on the remains of the missing boys,

(21:42):
not for any thoughtful reason, just because he thought he
could use it to bargain for better conditions for himself.
At this point, the families didn't care whatever would help
them get closure in the bodies of the young boys
back for a proper burial. And then, just thirteen days
in day his sentence, McRae was found dead of natural

(22:03):
causes in his prison cell, taking with him any answers.
The Florida families were devastated. Each one gave a short

(22:23):
interview with Florida Today in two thousand and five. Maria
Fleming talked about how she'd taken up painting beaches to
make her feel close to Keith and as therapy. She
told the paper that she added a picture of a
little bicycle in each of her paintings and said, quote,
I bought Keithy a bicycle because he thought he was

(22:45):
evil Canievil. He rode his bike down the stairs at church.
I guess you could say my painting is therapeutic end quote.
Kipling has Junior and his wife Anna just prayed for
closure in the disappears of their son Kip. They felt
that mcray had coached their son to leave the note

(23:05):
he did that day, and that he must have told
him something like we'll run away in the circus or something.
The circumstances of Kip Hess and Randy Laffer were quite
similar in that Regard and Randy Laffer was known to
love the circus in carnivals, and they all knew that
McRae did these traveling carnivals and that he did the
clown makeup and he did all of this stuff. Kip's

(23:28):
father said, quote, we try to be good Christians. We
hope in pray if Kip is dead, we hope that
he has gone to Heaven. I've prayed so many times
for some closure. If we could just find the remains,
we could have a memorial service.

Speaker 2 (23:42):
End quote.

Speaker 1 (23:44):
Mary Smith, mother of Charles Collingwood, said that although her
boy had been troubled, she prayed for him constantly. The
Quaker woman told the paper quote, I just turned him
over to the Lord. Whether he's gone or still here,
you have to believe he's in God's hands, and I
accept that. But I would like to know where the
body is. I'd like to bring him home.

Speaker 2 (24:06):
End quote.

Speaker 1 (24:08):
While the death of McRae might seem like a dead
end at finding resolution in these cases, I found something
promising while I was researching them. Michigan author Christy Lipka
is currently writing a book about the cases and hoping
to find people who knew both the victims and the
McRae family. Not only is she hoping to shed light

(24:28):
on what she and many believe are more victims out
there around the country, she also wants to bring the
remains of Kip, Keith and Charles home. So if you
have any information, please reach out to her. Her contact
information was listed in a recent article and her number
is seven three four six four five zero nine seven three.

(24:51):
She's willing to chat with anybody or set up a
time to me. I did search all over the country
to see if there were cases that were simp But
I haven't been doing the groundwork. She has been doing
over a longer period of time, and from what I
read in the article, she has identified, along with another
researcher who's helping her, they've identified several people who could possibly.

Speaker 2 (25:13):
Be mcray victims.

Speaker 1 (25:15):
One I'd like to just throw out there that has
never been publicly connected to McRae, but just seemed a
little similar to me. It was twenty year old John
Clifton Ballinger. He went missing in Statelee Beach, Florida, in
June of seventy seven. He was twenty years old at
the time, and he was in that general area that
McRae was in, and he had a similar appearance.

Speaker 2 (25:36):
To Keith Fleming.

Speaker 1 (25:37):
He had the long blonde surfer hair and according to
the website The Charlie Project, he was lasting on his
twentieth birthday. He spent the evening on a double date.
He was at the movie theater to see Star Wars,
and part way through the movie he told others he
was stepping out to use the restroom. He never returned
to his seat, and no one has seen or heard
from him since.

Speaker 2 (25:58):
When he vanished. He reportedly only.

Speaker 1 (26:00):
Had about fifteen dollars cash with him. Now, he does
have some outlying factors.

Speaker 2 (26:04):
He had been struggling in the months leading up to
that night. He was having some issues with drug.

Speaker 1 (26:08):
And alcohol use, and he had run away before as
a teenager, but this runaway pattern had not aligned with
what he did now and he was never found.

Speaker 2 (26:19):
And that's similar to Charles Collingwood.

Speaker 1 (26:20):
Charles Collingwood, his mother Mary said that he had also
run away before, but that he had kind of a
pattern he followed when he ran away, and that this
was just not the case.

Speaker 2 (26:29):
So it might be a little bit of a stretch,
but I wanted to float it out there.

Speaker 1 (26:34):
The suspect in these cases left behind a wake of devastation,
lost boys who had their whole future ahead of them.
While many of their relatives have since passed away, they
all have surviving family members and friends hoping to find answers.
It's not unheard of for perpetrators to escape accountability today,

(26:54):
but these cases are a prime example of unintended consequences
that come with lenient, recent and sing and reformative policies
around prison. And I say that as someone who supports
a lot of them and believes people can change, and
I love prison reform and law shifts that are well
thought out. But even if people can change, we have

(27:17):
to put the victims of these crimes first in their families,
and we have to shape any reform we do around
outcomes that align with their memory and the safety of
everyone they encounter in the future. I'm not here with
all of the answers, but i am asking that we
approach these topics with nuance and care and try to

(27:38):
protect one another and those most vulnerable in our society.
This has been another episode of a Simpler.

Speaker 2 (27:46):
Time True Crime.

Speaker 1 (27:47):
If you appreciate the work I'm doing, please leave a
five star review on your preferred listening platform. Word of
mouth helps me tremendously, so please tell a friend I
love case suggestions and partnering with families. Just send me
an email at Simpler Timecrimepod at gmail dot com.

Speaker 2 (28:04):
Thank you so much

Speaker 1 (28:05):
For listening, and see you again next Monday.

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Prime and Only Suspect Part 2: The Unsolved Disappearance of Kip Hess, Keith Fleming, and Charles Collingwood

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