The Wall Streeter’s Guide to Going to Prison

Bear Stearns execs Ralph Cioffi and Matthew Tannin were led off in handcuffs a couple of weeks ago, accused of deceiving investors in one of the firm's ill-fated hedge funds. Bayou Group founder Samuel Israel III turned himself in last week after spending a few weeks on the run, and has started a 20-year sentence for defrauding investors of $450 million. (He now faces an additional 10 years for bail-jumping.) Plenty of other financial big wigs may ultimately get caught up in criminal probes, making 2008 one of the busiest years for white-collar defense lawyers, at least since the Drexel Burnham boys headed to the clink in the early '90s. A word of caution, though, to high-finance criminals facing the prospect of time behind bars. You do not want to show up to prison totally unprepared a la Sherman McCoy in Bonfire of the Vanities. Certain matters should be taken into account before you head off to the clink. There are even ways to parlay your riches and master-of-the-universe shtick into preferential treatment! Tips for disgraced Wall Streeters on how to survive behind bars after the jump.

First off, you'll need to hire a "post-conviction specialist." This is an absolute must, and should be done long before you show up at the prison gates. For a high five-figure sum, a prison consultant will help minimize the time you spend behind bars, divert you to the cushiest facility possible, and prepare you psychologically for the shocking realization that for however long you're locked up, you will be forced to make do without your Blackberry and Starbucks frappucinos.

Like to play tennis? Your consultant might just be able to arrange a spot at one of the federal prison camps in California that has tennis courts on the premises. If, on the other hand, you're an alcoholic, your consultant may be able to help you get admitted to a rehab program in prison, which could even knock a few months off your sentence. Just ask Al Pirro, the husband of Jeanine Pirro. Your advisor can suggest a long list of other issues to take care of before heading to the slammer. Shoe designer Steve Madden, for example, made sure he had all necessary dental work done beforehand. Big shots of all stripes will print out their contacts on paper before they head to jail and then have someone mail them the document, since you can't take your Rolodex or PDA with you.

For the absolute crème-de-la-crème in prison consultants, the man you probably want to talk to is Herbert J. Hoelter. His illustrious client list includes Michael Milken, Ivan Boesky, Adelphia founder John Rigas, Alfred Taubman, and Martha Stewart. Do keep in mind, though, that unless you're headed to a state prison—and given what you've done, that's very unlikely—even a top-of-the-line prison consultant won't be able to arrange for conjugal visits.

A few other handy tips, based on the guides How to Deal With Being in Prison and Making It: A Prison Survival Guide:

The Wall Streeter’s Guide to Going to Prison

Don't Snitch
Okay, so ratting out your co-conspirators got prosecutors to drop four counts of securities fraud against you and shortened what could have been an unbearably lengthy sentence. But that kind of tattle-tale behavior is totally counterproductive behind bars. "If you see something illegal or violent, walk away and do not divulge any information if questioned later. Being known as a snitch will make bad things happen to you."

The Wall Streeter’s Guide to Going to Prison

Don't Cry
Breaking down on the stand may have showed you were a sentient human being with feelings rather than a remorseless thief who bilked investors out of millions, and may have scored you sympathy points with the jury and judge, but all it's going to do is put a big crosshairs on you in lockup. Be tough. Act strong. "The behavior of other inmates will intimidate you, but don't show fear."

The Wall Streeter’s Guide to Going to Prison

Work Out
Okay, so the bench press in the jail yard doesn't exactly stack up to the Equinox or the private gym you had in your Park Avenue apartment, but you're in no position to complain. At least this way, you'll have a real incentive to get in shape. As you fill out your nebbishy physique, it'll make you less likely "to be targeted as [a victim] for strong-arm tactics."

The Wall Streeter’s Guide to Going to Prison

Get Religious
You may not have cracked open a religious text since your Bar Mitzvah, but prison is a good place to rekindle your relationship with God, or at least to fake doing so by toting along a pocket Talmud everywhere. "Inmates tend to treat those always carrying a Holy Book and praying with more respect than others." And while there's nothing to do to make prison food taste like the work of your personal chef (or Daniel Boulud), ordering Kosher meals—even if you don't happen to be Jewish!—is a way to get ever-so-slightly more high-quality grub than other inmates. Oh, if the prison you're headed to doesn't offer the option for some reason, get in touch with the Aleph Institute. They'll strong-arm the prison into meeting your "dietary restrictions," especially if you make a large donation.

The Wall Streeter’s Guide to Going to Prison

Trust No One
Actually, your years on the Street should have prepared you well for this vital rule of prison life. "Remember, you are in a house of thieves, rapists, murderers, and liars, and you should not believe very much of anything you hear. Do not trust other inmates except in cases where there would not be serious consequences for doing so."

The Wall Streeter’s Guide to Going to Prison

Read a Lot
"They have a library there, so use it." If you're lucky, the library at your facility will have an especially thorough section of non-fiction books on white-collar crime. Reading these books will help you remember that others have been through this ordeal before and you are not alone—in fact, you're in good company! Read about the corporate misdeeds of Ivan Boesky and Michael Milken in Den of Thieves; Al Taubman and Diana Brooks in The Art of the Steal: Inside the Sotheby's-Christie's Auction House Scandal; and the Enron boys in Kurt Eichenwald's Conspiracy of Fools. Or if you're looking for a little pick-me-up, you might try Torture and Truth: America, Abu Ghraib, and the War on Terror. Remember: There are worse places to be confined!

The Wall Streeter’s Guide to Going to Prison

Don't Talk Politics
"Do not discuss politics or personal feelings about anyone." Bringing up that $25,000-a-plate McCain fundraiser you threw is not going to endear you to your cellmates. If you must bring up something politically-related, talk about how you supported efforts to roll back New York's draconian Rockefeller drug laws.

The Wall Streeter’s Guide to Going to Prison

Stay in Touch
Just because you're not allowed to keep a ThinkPad in your cell doesn't mean you can't communicate with the outside world. You'll have visitation rights, and on top of that you can write as many letters as you want. Remind people you exist! "You may be out of sight for a while, but there is no reason to stay out of mind."