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NARRATOR: 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.
NARRATOR: 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.
MERIT LAJOIE: 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.
NARRATOR: But in the spring of 1996,
Gayle's family noticed that she was behaving suspiciously.
MERIT LAJOIE: 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.
NARRATOR: On another occasion, Gayle
had refused to let her daughter drive her car.
MERIT LAJOIE: 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.
NARRATOR: Even a simple phone call set Gayle on edge.
MERIT LAJOIE: 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.
NARRATOR: 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.
[gunshots]
NARRATOR: He went outside and saw
a gunman standing next to her car.
He ran to call police.
NARRATOR: 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.
PAUL LOMBARDO: It was very close and personal.
And there was some indication that several of the wounds
were close contact type of wounds.
NARRATOR: And police noticed that Gayle's husband Doug was
holding a 22-caliber revolver, the same caliber
weapon used in his wife's ***.
-Well, naturally, we have a shooting.
He's at the scene with a gun.
Well, that's going to be the first place
you're going consider something.
NARRATOR: Doug claimed he grabbed his gun
for protection after he called 911.
Police asked Doug to describe the man he saw kill his wife.
-He thought that the subject that he saw in his driveway
was a Hispanic male, light-skinned male.
NARRATOR: But this contradicted his 911 call to police.
NARRATOR: 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 gunshots and the sound of a car speeding away.
-Very shocking, especially in this neighborhood.
NARRATOR: 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.
NARRATOR: When police arrived to the scene of Gayle Isleib's
***, her husband Doug was holding a 22-m caliber pistol,
the same caliber weapon used in her ***.
But the gun was fully loaded.
And this model did not discharge its spent shell casings
like the weapon used in the ***,
so Doug was eliminated as a suspect.
DENNIS O'CONNOR: 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.
NARRATOR: The assailant fired seven shots at close range.
Five of them struck Gayle Isleib in the head.
PAUL LOMBARDO: 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 shots at her.
NARRATOR: Family members and friends told investigators
that Gayle Isleib had no known enemies,
so they began their investigation
by talking to Gayle's coworkers.
DENNIS O'CONNOR: This is a group of crackerjack investigators.
Paul Lombardo went to Walmart the next morning,
7 o'clock when the store opened up.
And he started interviewing coworkers.
NARRATOR: 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.
NARRATOR: The employee was 25-year-old Tyrone Montgomery.
He was half of Gayle's age.
Yet that didn't seem to deter him.
DENNIS O'CONNOR: 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.
NARRATOR: 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.
MAN: 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.
NARRATOR: It looked like a criminal checklist.
But why did it mentioned using an icepick to kill a man?
Was it possible that the intended
target was Gayle's husband?
PAUL LOMBARDO: 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.
NARRATOR: 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.
NARRATOR: 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 ***.
PAUL LOMBARDO: Apparently he had made the comment
at the hospital that a friend of his had just died
and he was feeling suicidal.
NARRATOR: Or was this a ruse so he
wouldn't have to speak with police?
MERIT LAJOIE: 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.
NARRATOR: The prime suspect in Gayle Isleib's ***
was her coworker, 25-year-old Tyrone Montgomery.
PAUL LOMBARDO: 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.
NARRATOR: According to co-workers,
Montgomery asked Gayle Isleib several times
to go out with him.
When she refused, he exhibited bizarre behavior.
DENNIS O'CONNOR: He apparently either got a ride from her
or gave her a ride somewhere, pulled out a BB gun,
and said, see how easy it would be to hijack you,
and stuck the gun 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?
NARRATOR: 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.
NARRATOR: No one knows why Gayle kept quiet
and tried to handle the situation on her own.
MERIT LAJOIE: 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.
NARRATOR: Not long after committing himself
to the psychiatric hospital, Montgomery
granted police a brief interview.
PAUL LOMBARDO: We asked him about
whether or not he had killed Gayle Isleib.
And his denials were very calm and quiet, actually.
So that was kind of an interesting note.
NARRATOR: Montgomery ended the interview quickly.
So investigators asked the staff for the clothes he was wearing
when he checked into the hospital.
DENNIS O'CONNOR: 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.
NARRATOR: So any analysis was worthless.
But crime scene analyst Virginia Maxwell
examined the one item the hospital
didn't touch, Montgomery's boots.
VIRGINIA MAXWELL: 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 shots 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.
NARRATOR: 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.
VIRGINIA MAXWELL: 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.
NARRATOR: 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.
VIRGINIA MAXWELL: 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.
NARRATOR: So the evidence was consistent but not conclusive.
Police had a suspect.
But they still needed something to link
him to Gayle Isleib's ***.
With a warrant, investigators searched Tyrone Montgomery's
home, looking for the 22-caliber weapon
used in Gayle Isleb's ***.
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 ***."
We began to find parallels to what he had written
in his note, some of the things he
had done prior to the ***.
NARRATOR: 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.
NARRATOR: 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 bullets 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.
NARRATOR: Surprisingly, the marks on the casings
had a distinctive series of scratches under the rim.
To ballistic experts, this was clear evidence
that the gun 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.
NARRATOR: The ballistics evidence clearly
showed that the gun fired in Montgomery's basement
was the same gun used to kill Gayle Isleib.
Prosecutors believe that Montgomery was angry
when Gayle Isleib refused his advances,
so he hatched a plan to kill 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 gun.
[car horn]
Montgomery panicked, and fired seven shots into the car.
[gunshots]
As he fled, a tiny piece of glass was embedded in his boot.
Handwritten notes in his car, the bullet casings
in his basement, and the glass in his boot
tied him definitively to the ***.
PAUL LOMBARDO: You're finding the pieces here and there.
And you're starting to fit these pieces together.
And that's a really big piece.
NARRATOR: Tyrone Montgomery was arrested
and charged with felony ***.
Although police didn't need information
on how he got the weapon, they wanted it.
So they questioned once again the manager of the gun
department at Montgomery's store.
And this time, the manager admitted Montgomery bought
a 22-caliber rifle shortly before Gayle Isleib's ***.
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 rifle.
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 rifle.
NARRATOR: When the manager learned Gayle Isleib was killed
with a 22-caliber weapon, he panicked
and changed the store's logbook.
-What it would have done for Montgomery
was it would have given him a gun that was untraceable,
because there would have been no record of that gun
having been sold at that store.
NARRATOR: Now that police had the serial number,
they found the rifle in the possession of a local man who
had bought it as a second-hand gun.
Ballistic tests proved this was the *** weapon
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.
NARRATOR: In October of 1997, Tyrone Montgomery
was convicted of felony *** 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.