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A True Crime Breakdown of The New York Prison Break

Questions, Questions

Forget what we know (which isn’t much) about David Sweat’s and Richard Matt’s daring prison break. What are some alternate scenarios?

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On June 6th, murderers David Sweat and Richard Matt cut their way out of the maximum security Clinton Correctional Facility in Dannemora, N.Y., and so far, they haven’t been caught. Pretty much, that’s what we know for sure.

Most everyone I know has been fascinated by the dirty details of the breakout, myself included. I write true crime based exclusively on painstaking, fact-checked investigative journalism. This piece isn’t that (though I have asked some expert sources for opinions). I’m not playing dress-up as junior detective (though I have consulted about con behavior and fact patterns with some friendly investigators). Also, nope, I’m not a pop psychologist (though I have consulted with a defense psychologist who works with serial murderers).

This escape has all the makings of a great true crime story, except we don’t yet know exactly how they escaped or where they went or how, and the ongoing investigations are a black hole from which little news escapes.

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But homicide detectives taught me that when looking at a crime, it’s useful, and sometimes fun, to forget what you think happened. Just look at the facts, and ask yourself, are any other scenarios possible? Someday, maybe, we’ll get the answers. But until then, I’ve got some questions.

Question 1: Are we absolutely sure the break-out started from inside the prison?

Apparently,Matt and Sweat left their guarded maximum security prison by using hand-tools to cutthrough steel and brick walls, before somehow lucking into power tools left in a locked lockbox by contractors, which they used to cut a professional-quality porthole into a24-inch diameter, 3/8-inch thick steel steam pipe.

They then crawled through that pipe to the other side of the prison barrier wall, cut their way out again using those tools on an extension cord, then worked their way through a maze of duct work to finally emerge froma manhole on a dark and empty rural street. At which point they walked away and disappeared.

That sounds really difficult. And I’m sure it was.

Here’s what would be easier—popping a manhole on a dark and empty rural street and, gradually, breaking into the prison.

Doesn’t that sound relaxing? You could take your time. You could bring your own tools and power supply. Heck, you could even bring an acetylene torch, for where the extension cord wouldn’t reach. It would be a real help, especially working in that 24-inch diameter pipe. And you could make all the noise, dust, sparks and smoke you wanted. It wouldn’t bother anyone. You wouldn’t be in a prison full of former informants hoping for pleas deals and guards making bed checks every two hours.

Did that happen? Did they have an accomplice on the outside, maybe a professional to make those pro-grade steel cuts, with access to tools and plans and a Home Depot charge account? I don’t know, probably not. It just sounds easier.

But if I was breaking into prison, cutting a path for two murderers to escape, I’m sure I’d leave a note. Maybe a funny one, like we were digging our way to China. Not a racist one, of course, but something whimsical. And of course I’d want the fellahs to see it, and you can’t really keep a sticky note on wet concrete, so I’d need a magnet…wait, hold on…

Questions 2 and 3: What’s with the note? And, what’s with the magnet?

To the left of the cut pipe, prison officials found a sticky note with a grinning bucktoothed caricature in a conical hat and “Have a nice Day” in arced cursive below.

Most of the press reports called this a “mocking note to authorities”, but authoritiesseem to have pretty thin skin.

It’s like a grocery list on the fridge door reminding you to pick up “CANTALOPE and TOILET P”.

It’s like the least convict way of communicating, ever.

Yeah, the note is a bit weird. But not as weird as the fact that it’s affixed to the pipe with a magnet.

But first, the “Have a nice Day” part. That’s David Sweat’s handwriting, or at least the D’s are the same. He sent a note to a journalist in 2010 in the same elaborate cursive.

Really, David? The note was possibly Sweat’s last message to the world, his Scarface moment, the ultimate kiss off. Surely he would have known that, which is why it’s hard to imagine the rest of the sequence:

“OK, so I’m a cop killer, probably sociopathic, seems like, and a lifer, probably,but luckily locked up in an aging rural New York prison which has casual Fridays and employees that will sex me and give me breakout tools—a prison located, for some reason,conveniently near deep mountainous woods, major highways and freight rail lines, and the border of a foreign country. And, luckier still, I’ve managed to become besties with a smart and motivated killer who’s already broken out of prison, twice. This is my one shot at freedom. I get caught trying, that’s it, they move me somewhere else, I die in solitary. But before we stuff into that steam pipe, hold on—do you have a pen? And, uh, a magnet? Because I wanna write something, ironically.

That’s a possibility, I accept that. And let’s assume that their breakout packing list included“magnet for affixing mocking note.” That’s a possibility too.

But are we sure that before the note became a mocking, ironic farewell from the convicts to the authorities, it wasn’t something else first?

Examining the photos of the note, you’ve gotta start with the caricature. It’s cute, but racist. Also, racist but cute.

The circle looks traced. The face is made of straight lines, not drawn, but made of- what? Looks like black electrical tape. Little pieces. I’m positive that as we speak, someone is figuring where those come from. Something with little black adhesive strips. That part looks like prison art—lots of time, few resources.

Either way, I doubt it was Richard Matt who made it. In prison, Matt painted realistic oil portraits of famous people, and he’s pretty good. I’m sure his work will sell for a lot now. It’s got “Vice Magazine lobby decor” written all over it.

Sweat reportedly draws good schematics, he was known for it. He’s a lines-and-circles man. He also drew smiley faces on his letter to the journalist back in 2010, but they were very different than this, all googley eyes and dimples. Was he the cute racist artist? Maybe he’s into 6th grade notebook art. Maybe he never graduated to ZoSo and AC/DC. It seems possible; we’re talking about a guy wearing an “I packed a bowl with the devil” t-shirt in his arrest photo.

So, go ahead, leave a note. Leave a dumb one. Leave it on the pipe, or on the ground. The thing is, it doesn’t matter where you leave it.If you escape, they’ll look, no matter where it is. They’ll see it. The Governor will see it. Everyone laid over in an airport and watching CNN will see it.

You don’t need a magnet.

But to stick a note INSIDE a curved pipe, you do need a magnet.

But why would they stick a note inside the pipe? Is it possible the note—or notes—were waiting for them?

I say “notes” because Clinton County District Attorney Andrew Wylie told the press, “It’s my understanding there were other notes or markers in the tunnel system.”

I don’t know what he meant, he hasn’t clarified. So here’s a scenario:

A convict in the dark pipe system would like be a rat in a maze, trying to beat the clock. You get lost and can’t find your way back out before bed check, game over.

In this scenario, you’d want to leave a guide for which pipe to take. A guide you could take with you. One you could set up then pocket as you made trial runs in the maze. A ginger bread trail of bright yellow squares and arrows fixed with magnets.

Ideally the arrows would have a definitive direction. A circle with a triangle would do that.

They might also look like a face with a conical hat.

Later, your dipshit partner might draw on it.

So, did they lay a ginger bread trail for their rat-maze route through the guts of the prison with Post-Its and arrows so they didn’t get lost?

Or did someone, cutting in from the outside, leave a little “digging to China” note just inside the pipe, and a gingerbread trail of other notes for them to follow in the dark beyond the prison system, on their way to the manhole?

Of course, I have no idea. But here’s another possibility:

You’ve come down the manhole with your tools. You’ve cut into the steam pipe to help your pal break out of prison. Now you need to come through on the other side, and need to know the right place to make the cuts. There isn’t a lot of room for error, and you need to be specific in your placement. On the other side is your pal the convict, he needs to tell you where to start cutting. But how do you communicate across steel?

A magnet would do that. Put a needle up to the steel on the other side, a stud finder,whatever. Where the magnet is, the needle would move.

Or, let’s say you’re inside the pipe, cutting the door but not all the way through, so it’s like a trap door the convicts could punch through when the time was right and the forecast was for days of heavy rain.

Matt and Sweat could use the hand tools their depressing tailor shop lover had brought them, the chisel and hacksaw, finishing the job, and follow the trail of Post-It notes and arrows.

And, when they broke through, like two kids playing at digging to china, would they find a little note stuck with a magnet on the inside of the pipe? And would Sweat write something on it, and leave it by the pipe with the magnet?

It’s unlikely. But is it possible?

Question 4: Where are they now?

No idea. But wherever they are, logically, Matt has killed Sweat.

By “logically”, I mean sociopathic logic. Are they sociopaths? At the very least they’re borderline, in that they would happily trade your life for their convenience.

Obviously, I don’t know for certain that Matt killed Sweat, it could be the other way around. Either way,two convicts on the run are more vulnerable than one. Splitting resources while doubling exposure makes no sense—to sociopaths.

As for a body, that would beharder to find than a living person. It must have made Sweat sweat, when the guy nicknamed “Hacksaw,” for his method of disposing of bodies, asked for hacksaw blades from Joyce Mitchell.

Question 5: Joyce Mitchell, in general

I don’t know the woman. Apparently I’m the only guy in New York who doesn’t. Whether she was in love or lust or just a sucker for dangerous dudes, I don’t know, but somewhere along the way I guess she forgot that Matt and Sweat were literal prisoners of her small town, while she was just kinda stuck there metaphorically, career and hubby-wise. She was never going to escape, not really.

And while it’s speculative, so is everything else here, so I’ll take a flier:even on her days off from her prison job, Joyce Mitchell was the least free of any of them. If that wasn’t true before the breakout, it is now, non-metaphorically, since she was taken into custody. Turns out it’s tougher to break out of psychological prisons than real ones—in upstate New York at least.

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