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November 29, 2004
In a spectacular flameout after he retired from tennis, Roscoe Tanner deceived his friends and family and ended up penniless and in jail. Now he hopes to heal the wounds he's inflicted and repay all his debts--but it won't be easy
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November 29, 2004

Outside Looking In

In a spectacular flameout after he retired from tennis, Roscoe Tanner deceived his friends and family and ended up penniless and in jail. Now he hopes to heal the wounds he's inflicted and repay all his debts--but it won't be easy

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ROCK BOTTOM? That's tough to pinpoint, he says, sighing. So many lows to choose from. Rock bottom might have come when he walked into that Stygian cell in a German prison and realized that for the length of his stay he would be defecating in front of his cellmate. "Man," he says, "that was humiliating." The time he was arrested in front of all those fans at a senior tennis event, that was pretty embarrassing, too. And when his father, once his most ardent supporter, turned uncommunicative, that one really stung. No, wait, I've got it, he says. Here's the lowest moment of his odyssey: Immediately after he finished serving four months in a maximum security county jail in Florida on a grand theft charge, he was transferred to a New Jersey jail where he would serve five months for willfully withholding child support. For two weeks he sat on a TransCor bus--think Con Air on the interstate--that zigzagged along the Eastern Seaboard picking up other criminals who were being reassigned from one jail to another. The bus, with no air conditioning, was hotter than hell. At night the convicts either slept in their seats or, if they were lucky, bunked down at a county jail en route. They were allotted three meals a day, but there was a catch: Their hands never came out of restraints. Ever try eating McDonald's with your wrists locked at your waist? he asks. It's not real pleasant.

This is what it came to recently for Roscoe Tanner. The tennis star who once shared drinks with Prince Rainier on the French Riviera and dined with the Reagans in the White House was sitting on a bus near an exit ramp, positioning his chin at just the right angle so he could eat a Big Mac and some fries.

RoscoeTtanner is not, of course, the first retired athlete to turn his life into a Hieronymus Bosch canvas. But it's hard to imagine a less likely candidate to make an absolute mess of things. Tennis players just don't fall into the abyss--especially not a player born to the manor, with a Stanford diploma, a thick Rolodex of connections and, if that weren't endowment enough, movie-star looks and boundless reserves of charm.

As Tanner retraces his via dolorosa, you have to remind yourself that the eminently likable narrator of this story is also its protagonist, the man who is on probation in three states, has amassed a mountain of debt and is on tenuous terms with much of his family. By all outward appearances, Tanner conforms to the image of a former tennis star in the second set of middle age. He recently turned 53 but could easily pass for a decade younger. He's tan, fit and blessed by the tonsorial gods with a full thatch of light brown hair. He spends his weekends on a beach haven off the coast of Southern California called Balboa Island, where $1 million might get you a three-bedroom cottage. Holding court at a restaurant in late October, he is flanked by an assortment of friends and his blonde, younger third wife, Margaret. Tanner speaks enthusiastically of his job as a tennis teacher in Laguna Niguel. Margaret gushes that Roscoe is a "super dad" to her twin teenage daughters from a previous marriage.

During the meal there are occasional hints that something has gone terribly awry. A discussion about politics quickly fades when a member of the dinner party realizes that Tanner, as a convicted felon, might not be able to vote. Tanner passes on the bruschetta, casually mentioning that it reminds him too much of the weight he gained in jail eating little but white bread. When the check arrives, Tanner looks away--he can't cover the tab, so he doesn't even feign reaching for it. After the meal he and Margaret walk to a friend's pad where they are living until Roscoe can come up with the cash to pay the security deposit and first month's rent on an apartment.

But Tanner is delightful company, a funny, self-deprecating man who makes everyone feel comfortable. His voice, a rolling bass with a slight Southern twang, is nothing if not smooth. Mistakes, he concedes again and again, have been made. But he's "putting things back together," he's "picking up the pieces," he's "attending church regularly and doing the right thing."

You believe him. You root for him. It takes a conscious effort to consider the possibility that this could all just be the latest in his lengthy history of deceptions.

Lookout Mountain, Tenn., sounds like the kind of backwater town immortalized in country music ballads. It's not. With a median household income in excess of $100,000, it's one of America's most moneyed enclaves, a suburb of Chattanooga that sits on a promontory from which you can see seven states on a clear day. Even in a community steeped in wealth and status, the Tanners were a distinguished clan. They traced their roots to British royalty. Leonard Roscoe Tanner II, a successful attorney, had studied law at the University of Chicago and was friendly with Tennessee's leading politicians, right up to the governor. He and his wife, Anne, had two daughters and then a son, Leonard Roscoe III, who were raised in a succession of ever-larger homes, the last a doge's palace of more than 7,000 square feet.

Roscoe, as everybody called the boy, wanted for nothing. But neither was he spoiled. Leonard, a stoic father cut from the Atticus Finch mold, was, as we say today, old school. He insisted that his son perform chores and No, Ma'am and Yessir the adults. Leonard took a particular interest in his son's tennis, analyzing his losses as though they were complex legal issues. In 1966 the teenage Roscoe struggled in his matches and finally summoned the courage to confront the old man at the end of the year. "Dad, leave me to figure tennis out for myself," he said. "If I don't get better, I'll quit. But if I win a national title, you have to buy me a car." Leonard went along with that. Liberated from Dad and all the attendant pressure, Roscoe won four national titles in 1967. "My dad didn't get me four cars, though," he says. "I got one. A used white Pontiac Tempest."

Roscoe went to the Baylor School, a semi--military academy in Chattanooga with a powerhouse tennis team coached at the time by Jerry Evert, Chris's uncle. His teammates included Zan Guerry and Brian Gottfried, both of whom would play professionally. Roscoe was an unassuming kid with no discernible ego. "I honestly can't remember a single thing not normal about him," says Gottfried. "Just a nice kid from a nice family."

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