A woman was
ambushed in her own driveway.
Eyewitness accounts differed.
But a handwriting
expert found evidence
that she had a secret admirer
with a not so secret motive.
In the 19th century,
Manchester, Connecticut
was the silk capital
of the world.
Today the mills are
apartments, and the town
is enjoying growth
and new investment.
- I believe the population's
around 58,000 people.
We have a large retail center
in the north section of town
which draws a lot of
people into that area.
Manchester was home
for Gayle and Doug Isleib, who
had been married for a
little over three years.
They both had grown children
from previous marriages.
She was Grammy to anybody.
Her grandchildren
were her whole world.
Even my cousins
who have children,
they were her grandchildren.
We were a very close
family, very connected.
But in the spring of 1996,
Gayle's family noticed that
she was behaving suspiciously.
And I said
something to her about it.
I said, Mom, what
are you doing hanging
blankets from the windows?
And her response to me
was, well, you never
know who could be out there
looking in your windows.
On another occasion, Gayle
had refused to let her
daughter drive her car.
She parked behind me.
And I said, Mom,
where are your keys?
And she refused to
let me take her car.
She was like, oh, no, no, no.
Just move my car.
I don't have enough gas.
And she made up one
excuse after another.
Even a simple
phone call set Gayle on edge.
You could
tell when the phone rang
she was nervous
about it, about who
it might be on the other end.
- I think that she felt
like she was protecting us
by not exposing us to any
danger that might be around.
On April 30, 1996, Gayle
ended her shift at the
Walmart store around 10:00 PM,
then drove home.
Her husband Doug said he heard
Gayle pull into their driveway.
Then he heard a commotion.
He went outside and saw
a gunman standing
next to her car.
He ran to call police.
When police arrived, they
discovered Gayle Isleib had been
shot multiple times in the head
and was pronounced
dead at the scene.
Investigators found
seven 22-caliber shell
casings scattered
around Gayle's car.
It was very close and personal.
And there was some indication
that several of the wounds
were close contact
type of wounds.
And police noticed
that Gayle's husband Doug was
holding a 22-caliber
revolver, the same caliber
w*apon used in
his wife's m*rder.
- Well, naturally,
we have a sh**ting.
He's at the scene with a g*n.
Well, that's going
to be the first place
you're going consider something.
Doug claimed he grabbed his g*n
for protection
after he called 911.
Police asked Doug to describe
the man he saw k*ll his wife.
- He thought that the subject
that he saw in his driveway
was a Hispanic male,
light-skinned male.
But this contradicted
his 911 call to police.
He also mentioned robbery.
But Gayle's purse and jewelry
were still in her car.
Two neighbors corroborated
parts of Doug's story.
They heard the g*nshots and the
sound of a car speeding away.
- Very shocking, especially
in this neighborhood.
Another witness saw
a white car leaving the scene.
However, the one thing
everyone agreed on what
that Gayle Isleib
had no known enemies.
- You'd never think,
geez, somebody
must be stalking my mother.
I mean, it just never
would come to your mind.
- The first thought in my mind
was, how the heck are we going
to solve this thing, because
we really at the beginning
had nothing.
When police arrived
to the scene of Gayle Isleib's
m*rder, her husband Doug was
holding a 22-m caliber p*stol,
the same caliber w*apon
used in her m*rder.
But the g*n was fully loaded.
And this model did not discharge
its spent shell casings
like the w*apon
used in the m*rder,
so Doug was eliminated
as a suspect.
There was
no rhyme or reason to it.
The Isleibs seemed to be a
husband and wife who were just
minding their business,
living their lives.
Gayle was a devoted mother,
it's pretty obvious.
She was a devoted grandmother.
The assailant fired
seven sh*ts at close range.
Five of them struck
Gayle Isleib in the head.
One of the
things that we looked at
was the possibility
that maybe perhaps this
was a road rage
type of incident.
Maybe she cut someone
off on her way home
and the person wound up driving
and taking some sh*ts at her.
Family members and
friends told investigators
that Gayle Isleib
had no known enemies,
so they began
their investigation
by talking to Gayle's coworkers.
This is a group
of crackerjack investigators.
Paul Lombardo went to
Walmart the next morning,
store opened up.
And he started
interviewing coworkers.
Gayle worked
in the shoe department
and told coworkers
that a fellow employee
had been bothering her.
- I think some of the words
that the employees used
were that this person was
infatuated with Mrs. Isleib
and would just constantly
be talking to her
and harassing her.
The employee was
He was half of Gayle's age.
Yet that didn't
seem to deter him.
Montgomery
would come in on his days
off and hang around
the shoe department
and follow Gayle around
when Gayle was working.
It became obvious that
he was drawn to her.
And his feelings
were unrequited.
When police
entered Montgomery's home,
he wasn't there.
But they noticed a
white car like the one
described by witnesses.
It was registered to
Montgomery's stepfather.
Inside, in the
ashtray, police found
the remains of a
partially-burned note
and several pages
of intact notes.
Dogs.
Bring mace and duct tape
to tie up dog's mouth.
Come up with excuse.
I'm returning her cake dish.
Wipe down all weapons.
Get icepick from grocery store.
Get him subdued then stick
icepick through his ear.
It looked like
a criminal checklist.
But why did it mentioned using
an icepick to k*ll a man?
Was it possible
that the intended
target was Gayle's husband?
At this point, we had
no way of talking
to him about that.
So we had to find other means of
tying these notes into Tyrone.
So they sent the note
to forensic document examiner
Jim Streeter, along with
known handwriting samples
from Tyrone Montgomery's
employment application.
- There were numerous individual
handwriting characteristics
and habits that I observed.
We had the use of
almost a cursive J
in this print-style writing.
And often it almost
resembled a letter
L, a cursive letter L.
That was one letter.
There was a consistent use
of an entry stroke appearing
to the left of the perpendicular
in a lowercase E that
was consistent
throughout the writings
of both the questioned
and the known.
Streeter concluded that Tyrone
Montgomery had
written the checklist.
But where was he?
Investigators learned
that he checked himself
into a local
psychiatric hospital
shortly after Gayle
Isleib's m*rder.
Apparently
he had made the comment
at the hospital that a
friend of his had just died
and he was feeling suicidal.
Or was this a ruse so he
wouldn't have to
speak with police?
There
that are affected by one
violent act like this.
And this happened to take
the center of our world.
She was the center
of our family.
The prime suspect
in Gayle Isleib's m*rder
was her coworker, 25-year-old
Tyrone Montgomery.
Tyrone Montgomery apparently
worked in the department
right next to Mrs. Isleib.
He didn't have any kind
of criminal record.
But he was one of
those employees
that the other
people in the store
talked about as being a little
different or a little out
of the ordinary.
According
to co-workers,
Montgomery asked Gayle
Isleib several times
to go out with him.
When she refused, he
exhibited bizarre behavior.
He apparently
either got a ride from her
or gave her a ride somewhere,
pulled out a BB g*n,
and said, see how easy it
would be to hijack you,
and stuck the g*n in her
ribs, words to that effect.
- He was young, 25.
My mother was 54.
She had a family, married,
grown kids, kids older than him.
You know, what do you think is
going to become of all that?
You know?
Gayle never filed
an official complaint,
although coworkers say there
were numerous incidents.
- There were several
occasions where Tyrone asked
her out to dinner
and she refused.
One person indicated that
they saw Tyrone put his arm
around her back and she
pushed his arm away.
- It was obvious that
he had... at this point
was living some type of
fantasy and believing
that she was going
to go off with him.
No one knows
why Gayle kept quiet
and tried to handle the
situation on her own.
You know, I'm
really sorry that I couldn't
help her with that,
and that she felt
she had to deal
with it on her own,
because I know if that was me,
I would be terrified, terrified.
Not long
after committing himself
to the psychiatric
hospital, Montgomery
granted police a
brief interview.
We asked him about
whether or not he had
k*lled Gayle Isleib.
And his denials were very
calm and quiet, actually.
So that was kind of
an interesting note.
Montgomery ended
the interview quickly.
So investigators asked the staff
for the clothes he was wearing
when he checked
into the hospital.
As pursuant
to the hospital policy,
they had laundered the clothing
before it was handed over
to the Manchester
police department
via a search warrant.
So any analysis was worthless.
But crime scene analyst
Virginia Maxwell
examined the one
item the hospital
didn't touch,
Montgomery's boots.
When I was
examining those work boots,
I found a cut in
the sole, in which
there was a glass
fragment lodged.
- We knew that the suspect
was probably standing just
outside the driver's side window
when the first sh*ts were fired
at Mrs. Isleib and there was
a significant amount of glass
on the ground around that area.
And this would have indicated
that there was some transfer
of that glass onto his
boots from the crime scene.
But as investigators well knew,
there is automobile glass on
virtually every city street.
So Maxwell measured the
refractive index of the sample.
If you place a rod
into a glass of water,
it appears that the rod is bent.
And that's not because the glass
rod is actually bent.
It's simply because the
speed of light in water
is different to the
speed of light in air.
Therefore, our eye perceives
that the glass rod is bent.
The extent to
which the light changes
is known as the
refractive index.
Maxwell crushed both the
glass from Montgomery's boot
and the glass from Gayle's
car, then placed the samples
on separate slides with
silicon oil and heated them.
When the oil reaches the same
refractive index as the glass,
the shards seem to disappear.
This proved the refractive index
of the glass in Gayle's car
and on Montgomery's
boot was the same.
But when we do testing
with refractive indices,
the best we can say
is that that known
sample could have been
the source of that
questioned sample.
So the evidence was
consistent but not conclusive.
Police had a suspect.
But they still needed
something to link
him to Gayle Isleib's m*rder.
With a warrant, investigators
searched Tyrone Montgomery's
home, looking for
the 22-caliber w*apon
used in Gayle Isleb's m*rder.
But they didn't find it.
They did, however, find some
interesting reading material.
- We found some indications
that he had purchased
some books, books on
how to be a hit man.
And what they were were
these books on quote,
unquote, "how to
commit a m*rder."
We began to find parallels
to what he had written
in his note, some
of the things he
had done prior to the m*rder.
Montgomery owned
another book, entitled
"Methods of Disguise," a
possible explanation for why
Doug Isleib gave
conflicting information
about the assailant.
- It all began to
kind of fit together,
that the likelihood of him
wearing makeup at the time
was probably pretty good.
In the basement, investigators
found a makeshift firing range.
There were several 22-caliber
rounds in the walls,
and spent shell
casings on the floor.
The b*ll*ts recovered
from the wall
were too damaged for comparison.
But the casings on the
floor were compared
to the casings from
the crime scene.
Under a comparison microscope,
firearms expert Ed Jachimowicz
studied the marks
on each casing.
- Every time a cartridge was
cycled through the action
of the firearm, it
produced that very detailed
microscopic mark
on every cartridge.
Surprisingly,
the marks on the casings
had a distinctive series
of scratches under the rim.
To ballistic experts,
this was clear evidence
that the g*n was not
properly assembled.
- This particular
model of firearm
was a take-down, meaning that
you could break it into pieces
and transport it from
one place to another.
And it just wasn't
quite together properly.
Whoever assembled this just
didn't push the frame back
into the barrel tight
enough, so there
was about a millimeter
gap between the frame
and the barrel.
The ballistics evidence clearly
showed that the g*n fired
in Montgomery's basement
was the same g*n used
to k*ll Gayle Isleib.
Prosecutors believe that
Montgomery was angry
when Gayle Isleib
refused his advances,
so he hatched a plan to k*ll
Gail's husband with an icepick
and kidnap Gayle at gunpoint.
On the night of the crime,
he parked up the street,
disguised his
appearance, and waited
for Gayle to return from work.
When Gayle drove
into her driveway,
she saw Montgomery with the g*n.
Montgomery panicked, and fired
seven sh*ts into the car.
As he fled, a tiny piece of
glass was embedded in his boot.
Handwritten notes in his
car, the b*llet casings
in his basement, and
the glass in his boot
tied him definitively
to the m*rder.
You're finding
the pieces here and there.
And you're starting to
fit these pieces together.
And that's a really big piece.
Tyrone Montgomery was arrested
and charged with felony m*rder.
Although police didn't
need information
on how he got the
w*apon, they wanted it.
So they questioned once
again the manager of the g*n
department at
Montgomery's store.
And this time, the manager
admitted Montgomery bought
a 22-caliber r*fle shortly
before Gayle Isleib's m*rder.
Montgomery told him he
wanted it for hunting.
- I don't think you're going
to drop a moose or a deer
with a 22-caliber r*fle.
You might take down a squirrel.
You might take down a rabbit.
You might take down a pheasant
if you're a very good shot.
But you're not going to take
out any kind of animals,
game animals in this
part of the country
with a 22-calibear r*fle.
When the manager
learned Gayle Isleib was k*lled
with a 22-caliber
w*apon, he panicked
and changed the store's logbook.
- What it would have
done for Montgomery
was it would have given him
a g*n that was untraceable,
because there would have
been no record of that g*n
having been sold at that store.
Now that police
had the serial number,
they found the r*fle in the
possession of a local man who
had bought it as
a second-hand g*n.
Ballistic tests proved
this was the m*rder w*apon
and it had been
assembled improperly.
- Looking at the side or
the circumference surface
of the cartridge case,
the most obvious mark
in this particular case
was that accidental mark
left by that firearm not
being properly assembled.
In October of
was convicted of felony
m*rder and sentenced
to 65 years in prison.
It's difficult to know why
someone like Montgomery
would believe a kidnapping
plan like this would work.
But the science
spoke with certainty.
- In certain aspects he
did a lot of planning.
In certain aspects his
planning was pretty pathetic.
His covering of his
trail, I should say,
was pretty pathetic.
- This case probably was
more of a team effort
than I have really
encountered in all
the years I worked
as a detective.
- We were very lucky
that they were
able to preserve
certain evidence
and then do their
testing and come back
with some solid,
concrete undisputed facts
that just I think
made it very easy
for the prosecution to
really get a good conviction.
12x10 - Catch 22
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Documentary that reveals how forensic science is used to solve violent crimes, mysterious accidents, and outbreaks of illness.
Documentary that reveals how forensic science is used to solve violent crimes, mysterious accidents, and outbreaks of illness.