Criminally Yours: The Great Prison Break

Columnist Toni Messina discusses the New York prison break. There’s something romantic about a prison break, but what about the people left behind?

Whoever thinks that prisons are country clubs where inmates get three squares, a comfy bed and an activity room to spend their days, has never spend a day in state prison.

Prisons are horrible places. I’ve been to my share — state, federal, county — and no matter how old or modern or well-lit or well protected, I could not wait to get out of every one of them. They are stifling, claustrophobic places with an antiseptic sameness that makes you feel like a specimen in a petri jar.

You are scrutinized from the moment you enter. Photographed, ID’d, scanned and sometimes frisked. At Attica you can’t even get through the metal detector wearing a bra. The guard politely hands you a brown lunch bag and instructs you to go into Bathroom 1 where you take the bra off, put it in the bag, hand the bag back to the guard, then go through the metal detector. Once you’re done, you get to put back on the bra, but only in Bathroom 2. Why? In case you left contraband hidden in the bra in Bathroom 1.

The food stinks, there’s often no natural light, and privacy — unless you’re in the SHU (segregated housing unit) — is nonexistent. Even in the SHU, although you may not have a roommate, somebody’s always watching. With the cutbacks of any kind of educational/rehabilitative programs, the only activities available are bulking up in the postage stamp-sized “gym”, and thinking up ways to get out.

How anyone could escape from Clinton, the maximum security prison in Dannemora, N.Y., is beyond amazing. It’s practically unbelievable, except it happened.

Richard Matt and David Sweat must have been planning it for years, reeling in the correction officer or officers they needed, gathering spare parts to break through the walls, collecting cigarettes (or whatever else they bartered with) to trade for clothes, cash, equipment, and then biding their time till the right moment came.

They’re not the first to escape — that happened in 1974 when Bernard Welch and Paul Maturano scaled a 20-foot cyclone fence and made their way to temporary freedom. (One remained on the outside two years, the other a full six.)

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Since then prison security at Clinton got tighter, walls reinforced, video cameras installed, privileges repressed, and yet somehow, some 40 years later, it happened again, and this time with the complicity of Clinton personnel themselves.

But then, that makes sense. Because of the tighter security measures in the last few decades, it’s gotten harder for friends and families of inmates to sneak in contraband. Guards have an easier time. For the few truly corrupt, it’s also a great source of income. Inmates will pay top dollar for porn, cell phones, and any kind of drug. Guards often become friendly with the inmates. After all, they have the most contact with them and are in a position of power. An inmate’s rapport with a C.O. could make the difference on whether he gets his mail, his commissary, and his visits. I had a client who openly dealt pot in prison. The guards knew it and looked the other way. One, they were paid off. Two, stoned prisoners were mellower than pent-up ones.

But the guard(s) who aided the escape of Matt and Sweat were working on a grander scale. The escapees weren’t just looking for small favors, but big ticket items. Equipment that would get them through concrete; that could be hidden in their cells then reused. They also needed the perfect set up once outside – money, transportation, false identities—and it appears they had that, too.

There’s something romantic about a prison break. Two guys patiently using their wiles to outsmart “the system.”

My feelings go to the inmates left behind. The 2,000-plus guys still stuck in Clinton must be cursing their luck that they weren’t smart enough to think of a way out, because now their lives are twice as miserable. The guards are all under suspicion, so are angrier. The nascent friendships that developed between guards and inmates over the course of years will not only be discouraged but actively investigated and punished.

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Everyone is on “lock down.” The mothers, wives, children who planned on visiting their loved-ones will be told they can’t. The scant privileges like the right to receive letters or buy food at the commissary will be suspended until the facility conducts an internal investigation (as well as other State and Federal agencies that will be investigating this), and comes to some conclusions about how the escape happened.

Probably every other prisoner upstate is suffering the same fate from Attica to Four-Points.

Matt and Sweat will get caught, eventually, almost everyone does. It may take months or even years, but there’s always a slip up or a loose tongue, with the amount of bounty ($100K) on their heads.

In the meantime, it’s the guards and the prisoners left behind who will suffer the most.


Toni Messina has been practicing criminal defense law since 1990, although during law school she spent one summer as an intern in a large Boston law firm and realized quickly it wasn’t for her. Prior to attending law school, she worked as a journalist from Rome, Italy, reporting stories of international interest for CBS News and NPR. She keeps sane by balancing her law practice with a family of three children, playing in a BossaNova band and dancing flamenco. She can be reached at tonimessinalw@gmail.com or tonimessinalaw.com.