8 Tips for an Easier Prison Stay

When you might want to feign mental illness in the pokey, and why you never enter someone’s cell without permission.


SO THE FEDS NAILED you for insider trading. Or maybe you lied to a grand jury to cover for your boss. Either way, you’re about to trade your tailored suit for an orange jumpsuit, and you’re freaked. Your trepidation is the livelihood of prison consultants, who, for a fee, will help prepare you for a stint in the pokey. We asked a few of them to share their tips for surviving hard time.

Leggo your ego: Be humble. New prisoners will “lock eyes with the wrong person and have problems,” says Steven Oberfest, an ex-bouncer and personal trainer who won’t say what he did time for. “This is not Fifth Avenue and their penthouse anymore. They’re just a number.”

Hard knocks: Never enter someone’s cell without permission, says Steve Scholl, a former management consultant who now goes by the moniker Dr. Prison. “It’s about respect. People get killed over that.”

Presumed innocent: Don’t go asking what someone is in for, advises Oberfest. Ask what he’s accused of.

Ethnic cleansing: Don’t mix with prisoners of other races, Dr. Prison warns. “Things we don’t even consider a problem between races here are a very extreme focus inside. If there’s a fight, every race needs to depend on their own race to protect them.”

Sleeping dogs: “Miserable people want to be miserable…treat them with extreme caution,” advises Robert McDorman, a former Texas car dealer who did 26 months for federal bank fraud.

The best defense: Just in case, Oberfest says you must learn to “drop someone incredibly fast.”

Unwanted interest: Says Oberfest, “If you bum a smoke and the guy with the cigarettes says, ‘Sure, it’s a twofer,’ you should know a twofer means, ‘I give you one for two, so now you owe me.'”

Alone time: Oberfest advises high-profile clients such as politicians to request solitary confinement, or even feign mental illness to get into the psych ward. “If you’re segregated, you’re going to have a much easier time.”

The Mojo Prison Guide Menu

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