Catch 22

Charlie Sheen is an icon of decadence.

I lit the fuse and my life turns into everything it wasn't supposed to be.

He's going the distance.

He was the highest paid TV star of all time.

When it started to change, it was quick.

He kept saying, no, no, no, I'm in the hospital now, but next week I'll be ready for the show.

Now, Charlie's sober.

He's gonna tell you the truth.

How do I present this with any class?

I think we're past that, Charlie.

We're past that, yeah.

Somebody call action.

AKA Charlie Sheen, only on Netflix, September 10th.

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 population is 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 Gail and Doug Islib.

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, Gail'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, Gail 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's 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 Gail 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 30th, 1996, Gail ended her shift at the Walmart store around 10 p.m., then drove home.

Her husband, Doug, said he heard Gail 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.

He sent your mercy.

There's a robbery here.

I think somebody shot at my wife.

I just saw somebody there with a batch.

When police arrived, They discovered Gail Islib had been shot multiple times in the head and was pronounced dead at the scene.

Investigators found seven.22 caliber shell casings scattered around Gail'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 Gail's husband, Doug, was holding a.22 caliber revolver, the same caliber weapon used in his wife's murder.

Well, naturally, we have a shooting.

He's at the scene with a gun.

Well, you're going to,

that's gonna be the first place you're gonna, you know, consider something.

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, a white-skinned male.

But this contradicted his 911 call to police.

I just saw somebody there with a bag.

He also mentioned robbery, but Gail'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.

Another witness saw a white car leaving the scene.

However, the one thing everyone agreed on was that Gail Islib 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, you know, how the heck are we going to solve this thing?

Because we really, at the beginning, had nothing.

When police arrived at the scene of Gail Islib's murder, Her husband Doug was holding a.22-caliber pistol, the same caliber weapon used in her murder.

But the gun was fully loaded, and this model not discharge its spent shell casings like the weapon used in the murder.

So Doug was eliminated as a suspect.

There was no rhyme or reason to it.

The Islip seemed to be,

you know, husband and wife who were just minding their business, living their lives.

Gail was a devoted mother.

It's pretty obvious.

She was a devoted grandmother.

Family members and friends told investigators that Gail Islip had no known known enemies.

So they began their investigation by talking to Gail's co-workers.

This is a group of Cracker Jack investigators.

Paul Lombardo went to Walmart the next morning, 7 o'clock when the store opened up, and he started interviewing co-workers.

Gail worked in the shoe department and told co-workers 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.

Islieb and would,

you know, just constantly be talking to her and harassing her.

The employee was 25-year-old Tyrone Montgomery.

He was half of Gail'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 Gail around when Gail was working.

It became obvious that

he was 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 Mason duct tape to tie up dog's mouth.

Come up with excuse.

I'm returning her cake dish.

Wipe down all weapons.

Get ice pick from grocery store.

Get him subdued and stick ice pick through his ear.

It looked like a criminal checklist.

But why did it mention using an ice pick to kill a man?

Was it possible that the intended target was Gail'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 question and the note.

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 Gail Islib's murder.

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 are so many people that are affected by one violent act like this.

And this happened to take, you know, the center of our world.

She was the center of our family.

The prime suspect in Gail Islib's murder was her coworker, 25-year-old Tyrone Montgomery.

Tyrone Montgomery apparently worked in the department right next to Mrs.

Islib.

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 Gail Islib 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 gun.

And said, see how easy it would be to hijack you.

And stuck the gun in her ribs, words to that effect.

Gail never filed an official complaint, although co-workers 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, you know, go off with him.

No one knows why Gail 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 killed Gail Isle,

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.

Guess pursuant to hospital policy, they had laundered the clothing before it was handed over to the Manchester Police Department via 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.

And 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.

Isleep, 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 Gail'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 Gail'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 questing sample.

So the evidence was consistent, but not conclusive.

Police had a suspect, but they still needed something to link him to Gail Islib's murder.

With a warrant, Investigators searched Tyrone Montgomery's home, looking for the.22-caliber weapon used in Gail Islib's murder, 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 hitman, and what they were were these books on, quote-unquote, how to commit a murder.

We began to find parallels to what he had written in his notes, some of the things he had done prior to the murder.

Montgomery owned another book entitled Methods of Disguise, a possible explanation for why Doug Islip gave conflicting information about the assailant.

It all began to kind of fit together that, you know, 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 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 Jakimowicz studied the marks on each casing.

Every time a cartridge was cycled through the action of their 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 gun was not properly assembled.

This particular model of firearm was a takedown, meaning that you could break it into two 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 gun fired in Montgomery's basement was the same gun used to kill Gail Islip.

Prosecutors believe that Montgomery was angry when Gail Islip refused his advances, so he hatched a plan to kill Gail's husband with an ice pick and kidnap Gail at gunpoint.

On the night of the crime, he parked up the street, disguised his appearance,

and waited for Gail to return from work.

When Gail drove into her driveway, she saw Montgomery with the gun.

Montgomery panicked and fired seven shots into the car.

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 murder.

Tyrone Montgomery was arrested and charged with felony murder.

Although police didn't need information on how he got the weapon, they wanted 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 Gail Islib's murder.

Montgomery told him he wanted it for hunting.

When the manager learned Gail Islib 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.

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 murder 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.

In October of 1997, Tyrone Montgomery was convicted of felony murder 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've 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,

you know, undisputed

facts that, you know, just I think

made it very easy for the prosecution to really get a good conviction.