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What Eight High-Profile Inmates Learned In Prison

With all respect to Dr. Laura and Dr. Phil, there are other seasoned experts with life lessons aplenty: those who served time in a cell. Here's some hard-won and at times hilarious perspective (if not redemption) from eight high-profile inmates.

Make Your Bed

Beloved stoner comedian and film star Tommy Chong (of “Up in Smoke" and “Half Baked” fame) drew some surprisingly practical conclusions from his time in the joint. In 2003 his Chong Glass/Nice Dreams firm---which sold drug paraphernalia, was financed by Chong and run by his son Paris---was snared in a sting operation. Instead of going to trial, Chong took a plea deal where he admitted distributing bongs and water pipes on the Internet. Despite his cooperation, Chong was sentenced to nine months in federal prison. “The number one lesson I learned is that the system is totally stacked against the citizen,” says Chong. “If you’re indicted for anything by the government my advice is to save your money, don’t spend it on an expensive lawyer." Oh, yeah, added Chong: “I learned how to make a bed and how to pick up garbage. And now I make the bed at home, my wife loves it.”

Get Your Head Straight

Heidi Fleiss soared, crashed and burned all in her 20s. The Hollywood Madam was arrested for pandering in 1993. Three years later Fleiss was convicted of federal charges of tax evasion, sentenced to seven years in prison, but released in 1999. "I was arrested when I had Mick Jagger and Prince dancing in my living room,” Fleiss said. “To go to jail seemed like a death sentence." Before being sent to prison, Fleiss lived in the federal detention center in downtown Los Angeles. She was protected by a “tough white girl” named “Skipper” who gave her some jailhouse wisdom: “Hit ‘em hard, hit ‘em fast and hit the biggest one first.” Getting sober and working out (Fleiss ran at least seven miles a day seven days a week) helped, too. She also worked on her state of mind. “It’s all relative," she says. "You can be just as happy in solitary confinement as you could be on a private island or a first-class jet. It all matters how you are in your head, your state of mind, how you feel."

Deal With You--Now

In 1988 Bruce McNall, former owner of the Los Angeles Kings, turned the sleepy hockey franchise into an entertainment phenomenon by landing Wayne Gretzky. While McNall had all the flash, he lacked the cash, defaulting on more than $200 million in loans. In 1994 he pleaded guilty to five counts of conspiracy and fraud, and he was released in 2001. “In a funny way you learn a lot about yourself [in prison]," says McNall. "You have a lot of time to think about that, to think about nothing but that, what went right, what went wrong, in your business and your life.” McNall concluded that he suffered from measurable insecurity. “I wanted to make everybody happy,” he says.

It's Not About The Highs And Lows

Before Michael Vick, before Plaxico Burress, before Nate Newton, there was Eugene “Mercury” Morris. The speedy running back and kick returner for the undefeated 1972 Miami Dolphins was convicted of cocaine trafficking in 1982 and sentenced to 20 years in prison, but his conviction was overturned four years later by the Florida Supreme Court because key evidence was suppressed. (Morris pleaded guilty to a reduced charge and was sentenced to the time he served.) Today Morris remains a hero to many for volunteering to obtain benefits for retired gridiron stars, who Morris believes have been cheated by the NFL. His advice to the struggling masses: “I’ve been to three Super Bowls and I’ve been to prison,” he says. “It’s not about the highs and the lows. It’s about who you are and where you are.”

What Doesn't Kill You...


In 2006 then Alabama Governor Don Siegelman was convicted of bribery and conspiracy, and served nine months of a seven-year sentence. During the trial news outlets questioned the charges, given that Siegelman was a Democrat in a Republican state. Three years later, 91 former attorneys general signed a petition asking Attorney General Eric Holder to throw out the conviction, but that request has been ignored. "The most frightening thing [about prison] is your rights are taken away," says Siegelman. "Whatever rights you have are what the prison guards decide what they want to give you. It goes on with food or medicine or anything else." The upside for Siegelman, a second-degree black belt in karate: "I hit much harder now thinking about those that lied to convict me."

Anger Can Be Poison

Michael Lohan, like his incorrigible starlet daughter Lindsay, was no stranger to trouble. As a stockbroker, he was convicted of criminal contempt of court in 1990 and served three years in prison. He did an additional year after violating his probation for leaving the state to visit Lindsay, who was ill, in 1997. In 2005, he was back in the clink after fighting with a guest at his son Dakota's confirmation held his Long Island home; he was released in 2007. He appeared on “Celebrity Rehab with Dr. Drew” in 2011 to receive treatment for alcoholism. Of his (first) time in the can, Lohan says: “It teaches you what it’s like to be alone and not have access to the people you love." He concedes that anger issues (and some cocaine abuse) were to blame. "I stuffed a lot of things inside that I thought were resolved," he says.

Challenge Your Assumptions

Thomas "Hollywood" Henderson, former Pro Bowl linebacker for the Dallas Cowboys, had a rare combination of size, speed and ferocity. He also had an addiction to drugs and alcohol, which got him booted from the NFL in the prime of his career. In late 1983 he was arrested with two teenage girls while smoking cocaine, accused of sexual assault and eventually served 28 months in prison. "The shame itself almost killed me," he says. Henderson says he has been sober for 20 years. He now sells motivational films of his experiences and speaks about his recovery. "Too many of us grow up believing that in order to have fun in life, you must have a drink or a drug," he says. "I deal in facts, and sobriety is also an option."

Life Moves In One Direction

When contacted for this story, Michael Milken, former junk bond king and philanthropist, demurred. His spokesman replied: “Mike is focused on the future---curing disease, fixing the economy, reforming education--- not on the past.” For some, that may be the best advice of all.

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