by Geoffrey Gray

"I don’t stress," Mike Tyson said. He was lying awake a little past 4:30 a.m. Los Angeles time in his room at the Beverly Wilshire Hotel. The looming assault charges awaiting him in his native Brooklyn seemed a continent away.
"You die too young that way," he said. "I learned that from a friend. Never stress about anything you can’t change."
Indeed, Mr. Tyson can’t change what Brooklyn prosecutors have on videotapes made from surveillance-camera footage at the Marriott in downtown Brooklyn in the early-morning hours of June 21, when a pair of allegedly drunken autograph-seekers approached him in the hotel lobby at 5:30 a.m. They teased Mr. Tyson into a fight and, after Mr. Tyson chased them down with a stanchion from the hotel lobby, all soon wound up in the hospital—in handcuffs.

Given his lengthy rap sheet, if he’s found guilty of the misdemeanor charges, Mr. Tyson stands to face up to a year in prison. So far, he’s spent far more time behind bars than any other popular boxing champion. In the early 1990’s, Mr. Tyson spent three years in prison after an Indianapolis jury convicted him of raping beauty-pageant contestant Desiree Washington—a charge Mr. Tyson adamantly denies—and was suspended from boxing for virtually 18 months after twice biting the ears of boxer Evander Holyfield in a 1997 rematch. Another prison term for the fighter, who is said to suffer the entire spectrum of human emotions—severe depression, kindness, generosity, rage and moments of comical, sparkling genius—might be too much for him to handle, many confidants say.

"Mike has always been looking for an escape, a trap door," said Teddy Atlas, one of Mr. Tyson’s first trainers. "He always lacked one essential ingredient in situation building character: the ability to confront himself."

The fight of Mr. Tyson’s life has moved from the boxing ring to the courtroom once again, and he’s throwing it, confidants and advisers say. Mr. Tyson’s newfound, stoic acceptance of his has turned into a dark fatalism, as his fortunes are drowned in debt and the prospect of a real comeback in boxing seems to recede further from his grasp. He doesn’t return calls to his lawyers to discuss the assault, and a plea-bargain is out of the question, even though in these sorts of reciprocal-assault cases, both parties usually plead themselves down to community service. His lawyers will be back in court Dec. 19.

Mr. Tyson remains boxing’s biggest, most lucrative fighter, no matter who the opponent. Naturally, his unpredictability fuels his drawing power. But to reclaim his fortune and change his reputation in boxing circles as a consummate slacker, Mr. Tyson must force his way back into fighting shape and mount (and market) the comeback. There are still glory days to come.

More time behind bars might spike any comeback dreams Mr. Tyson may harbor in some secret chamber under his tattooed, usually knitted brow. It will certainly kill any immediate chance the boxer might have to earn enough quick money to promptly pay off the nearly $40 million he owes to a melange of debtors, including over $300,000 for limo services; over $30,000 to a Hawaii resort; over $170,000 to a Las Vegas jeweler for a gold necklace with 80-carat diamonds; millions to his many lawyers and managers and consultants, many of whom continue to prey upon Mr. Tyson’s earning potential, mood swings and financial naïveté; and a hefty $13 million unpaid tab to the I.R.S.

When Mr. Tyson’s periwinkle Rolls Royce pulled up beside the courthouse doors Nov. 31, the anxious gallery of paparazzi expected the famously dapper fighter to step out of his car in a nimbus of bling-bling. Instead, the bankrupt former heavyweight champion emerged from behind the tinted windows of the $330,000 limousine in a pair of blue jeans faded almost to white, a T-shirt and a pair of sneakers.

In court, Mr. Tyson yawned throughout the entire session.

"I’m just trying to take it nice and easy," Mr. Tyson said in an interview before his appearance. "Nice and slow—that’s me."

Isn’t Mr. Tyson enraged that news of this summer’s assault—an attack that even his prosecutors in the Brooklyn District Attorney’s office say he didn’t initiate—made the covers of two daily newspapers in New York and blitzed CNN and other media outlets around the world?

"It doesn’t bother me," Mr. Tyson said about his Godzilla-like play. "They’re gonna write what they want to write—what they need to write."

On the phone, he did not want to talk about the two punks who ambushed him, his boxing future, his bankruptcy or any of the serious, life-altering decisions he must make in the coming months—or allow to be made for him.

Instead, Mr. Tyson wanted to talk about one of his heroes, Arnold Rothstein, the famed underworld mastermind, pool shark and gambler widely believed to have fixed the outcome of the 1919 World Series. Often, when Mr. Tyson checks into the many hotel rooms across the country in which he now lives, he can be found under the name Rothstein, or his other nom de guerre, Jack Dempsey, the hobo heavyweight legend who’s Mohawk hairdo Mr. Tyson sought to mimic when he became boxing’s youngest, perhaps most devastating heavyweight champion at age 20 years and five months.

"All those cats are my heroes, my idols," Mr. Tyson said. Asked why, he replied, "Because they didn’t give a fuck about nobody. Nobody."

Mr. Tyson’s crush on history’s lawless heroes and self-made pugilists dates to his teen years. Today, he’s one of the fight game’s premier historians: names, dates, wins, losses, Mr. Tyson knows the inside dope on virtually any fighter in the bare-knuckle and modern eras, and when he’s telling these dusty tales about the ghosts of boxing past he knows so well, sometimes for hours on end, Mr. Tyson seems to foam at the mouth.

"They were like the Marc Riches and the Bill Gateses," he said. "They were cool customers, like the mice that lay back in their holes and wait to eat their cheese."

Mr. Tyson has always seen in his heroes of early boxing, particularly the crafty Jewish fighters who boxed their way out of the same neighborhood where he spent his troubled youth—Brownsville—where he was arrested a reported 38 times between the ages of 10 and 13, mugging victims with "a cunningness." His sister Denise and brother Roger were said to have tied him to bedposts with rope, after which they tried to beat the bad out of him. Finally, he was sent to a reformatory upstate, the Tryon School, where he met the half-blind boxing sage Cus D’Amato. The rest was the stuff of classic boxing fairy-tales.

Now, he was talking about lightweight champ Benny Leonard and his set.

"Even though they were Jewish, they were very tribal, and there were all different kinds, Jewish fighters from Russia, the Balkans, Lithuania; they had different styles and different basic ways to even study their religion. They wanted to be classy, they wanted to be accepted by society—and people looked at them as being Uncle Toms, but really it was evolution, just ethnic groups evolving."

Mr. Tyson also indulges himself in the contradictory pasts of ruthless conqueror Genghis Khan and dove-like tennis great Arthur Ashe, whose likeness is tattooed on his torso alongside that of Chairman Mao’s.

Everyone is willing to pay triple to see Mr. Tyson fight a mega-matchup against the speediest, most accurate fighter in the game now, Roy Jones Jr. Can he shed the weight and make it happen?

Mr. Tyson asked his own question: He wanted to know whether numbers guru Meyer Lansky (a Rothstein protégé) had a connection to Leonard. If so, what was it?

"I haven’t seen that anywhere," Mr. Tyson said. "He must have."

Would he trade places with Rothstein or Dempsey or any of the historical ghosts he admires?

"It’s not better to live in a time like that," he said. "It’s just better to know that people lived in a time like that. We need to escalate our humanity towards people. Just think of what one human being does towards another human being now … it’s catastrophic! It would even be a disgrace to a nation of heathens, what people do now—the disrespect, the hate. People say they’re loving the world, but really, it’s overshadowed by so much hate."

All celebrity court dramas seem to carry at least one signature piece of evidence. For O.J. Simpson, it was a glove; for Bill Clinton, it was a blue dress; for Kobe Bryant, a pair of yellow panties. For Mr. Tyson, this time around, prosecutors have hinted that part of their case could rest on Mr. Tyson’s jacket.

Look at the in-house security videotape from the lobby of the hotel that morning, veteran Brooklyn Assistant District Attorney John O’Mara might say in court. Sure, the grainy, hard-to-follow images show Mr. Tyson getting accosted. One can almost smell the boozy breath of the so-called autograph-seekers, Sam Velez, 30, and Nestor Alvarez-Ramos, 24, both of Philadelphia.

"You’ve got fists, we’ve got guns," the two men said, according to both the prosecutors and Mr. Tyson’s attorneys.

Then the action starts. The images jut back and forth. Soon, within the hard-to-follow frames, the two are on the ground and Mr. Tyson is still standing. But why, Mr. O’Mara might argue at this point, why would Mr. Tyson then choose to take off his jacket (to increase mobility?) and pounce on the two men again?

"At first, we believe, Mr. Tyson acted in good faith to defend himself," Mr. O’Mara said. "But this went way beyond."

After Brooklyn cops broke up the mêlée, Mr. Velez was rushed into emergency oral surgery. His two front teeth had been smashed into his gums, claims his attorney, Earl Brown, and root-canal surgery had to be performed. He was also left with 12 stitches over his right eye, and now Mr. Velez can’t feel the right side of his face, said Mr. Brown; it’s gone numb. The other friend took less of a beating, Mr. Brown continued, though a beating all the same: Mr. Ramos suffered a twisted ankle, a sore skull, a few face cuts and nasty, pounding headaches. Mr. Tyson cut his hand.

"It could have been worse," Mr. Brown said. "But still …. "

Not so, said Mr. Tyson’s legal team, composed of the always-bowtied Mel Sachs and Steve Brounstein, a stubble-chinned criminal attorney. They feel they have a knockout case on their hands, even if Mr. Tyson doesn’t necessarily have the juice to pay them—yet.

They’ve filed motion papers to have the case dismissed and will argue those merits in court on Dec. 19.

"Mike isn’t necessarily clear why he was arrested in the first place," said Mr. Sachs, who’s represented magician David Copperfield, hip-hop impresario Russell Simmons and comedian Jackie Mason over the years. Mr. Brounstein, a former Bronx district attorney, said, "These guys were only after a payday."

That could mean big money someday—if Mr. Tyson had any—and Mr. Tyson’s attorneys say they have and will continue to rebuff any attempts to settle. Of Mr. Tyson’s cavalier removal of his coat, Mr. Brown said: "It’s our position that Mike made no effort to remove himself at any point from this situation at any time. He initiated it, and he concluded it."

Asked about Mr. Tyson’s removal of his coat, Mr. Sachs said the action was "an atavistic response" from a street-bred fighter who, given the circumstances, "showed restraint."

"What should Mike have done?" Mr. Sachs said. "Walk out the front door and wait for them to shoot him in the back?"

There is also the issue of motive. Mr. Sachs’ private investigator, a former New York Police Department detective named Mike Charles, has identified at least one witness, Mitchell Swindell, who spent the night with Mr. Tyson’s assailants in the Brooklyn holding pen. Mr. Swindell, arrested on a domestic-assault charge that night, remembers the two bragging to anybody who would listen that, with a little luck, they might score a high-stakes settlement deal.

"This is a ghetto thing," Mr. Swindell told The Observer. "Those two knew what they were doing from the get-go."

But Mr. Brown denies that his clients chose to pick a fight in order to make money.

"We all like money," Mr. Brown said. "But taking a series of Mike Tyson punches in order to secure it? I don’t think so."

When Mr. Brown first chose to take Mr. Velez and Mr. Ramos on as clients, he said, he had already left his brief legal career (filing a resignation with the Legal Aid Society after one year of service) and taken a job teaching business classes at the University of Virginia, where he currently works. The surprise referral to take on his first private case came through a former employer in the "club party-promotion scene," he said, though he wouldn’t identify the person. Mr. Brown also shrugged off any suggestion that representing both of Mr. Tyson’s alleged assailants may constitute a conflict of interest. He’s filed papers with the court to dismiss the menacing charges, which carry a maximum sentence of 90 days in prison. After the criminal charges are dropped, he said, his clients will file a civil suit against Mr. Tyson for their wounds.

Someone will have to take some Mike Tyson punches soon—or Mr. Tyson’s money will run out completely. He’s been virtually homeless for the last eight months, traversing the country, from Los Angeles to Miami to Phoenix to Brooklyn, hanging out with friends and sleeping in hotels and entertaining short-money business propositions, like fighting a 7-foot-6, 385-pound former funeral-home carrier turned martial-arts star in Japan. Since he filed for bankruptcy on Aug. 1, Mr. Tyson’s only physical assets—including his Las Vegas manse, a home that sits in the lot next to the Shenandoah ranch of crooner Wayne Newton—have been seized and will be sold, according to Mr. Tyson’s former manager, Shelly Finkel, who chairs the boxer’s creditors’ committee.

"It’s sad, almost surreal," Mr. Finkel continued. "He’s just vacillating."

Mr. Tyson’s wanton spending has also been shackled by tax liens. At this point, his money, or the fading memories of it—including the Versace-inspired bathtub he purchased for $2 million for first wife Robin Givens, which came encrusted in diamonds; the $20,000 wads he used to hand out to bums and derelict fighters in casinos; the cars and motorcycles and Siberian tigers; and the over $100 million in earnings that he claims was siphoned away by promoter Don King through dubious accounting—now seems like an unnecessary distraction.

In many ways, wealth has always made him uncomfortable. Mr. Tyson’s chauffeur, Rudy Gonzalez, said that when he and the boxer first went into the basement of an old Vanderbilt cottage that Mr. Tyson purchased in Bernardsville, N.J., many years ago, they found cases containing a vintage-wine collection.

"Man, get all this shit out of here," Mr. Tyson, then 21, told Mr. Gonzalez. "I want to build me a gym."

Mr. Gonzalez remembers packing those crates onto a truck and driving back to Brownsville, where he and Mr. Tyson and other members of their team unloaded what might have been the Vanderbilt family’s wine collection and handed the dusty bottles out to friends and bums—whoever happened to be walking by.

"He was like the Robin Hood of the ghetto," said Mr. Gonzalez, who handled the fighter’s 250-strong exotic-car collection early on in Mr. Tyson’s career and now rents Ferraris and Lamborghinis to tourists in a shop off the beaches of Fort Lauderdale, Fla.

Besides, Mr. Tyson never had an interest in saving or showed a penchant for arithmetic. When he first met Joseph Maffia, his accountant at Don King Productions, who is of mixed-race descent, Mr. Tyson didn’t inquire about his Roth I.R.A. "So," Mr. Maffia remembered Mr. Tyson asking him, "do you have a big dick or a little dick?"

The life seemed funnier then, when Mr. Tyson was young and hungry to take on challenges to his title, and there was lots of money around to buffet him along. Now Mr. Tyson’s advisers and businesses managers change often. There are those who dive into his cell phone periodically to look at the numbers he has stored and weed out undesirables—like reporters. But Mr. Tyson seems to pay little attention to those still trying to eke a living off him. What he wants most now are the things he chose to ignore in his prime, many around him say: security, peace, a real life. He wants some time to watch his kids grow, to hang out on the stoop with old friends, to smoke a little pot, to talk shit.

"There’s not one person in the country Mike feels like he can trust," said one confidant. "He’s the loneliest fucking guy out there."

Two weeks ago, in the snowy midst of a wild blizzard, Mr. Tyson resurfaced. It was well past midnight and, in the bowels of Madison Square Garden, in the midst of a post-fight press conference, Mr. Tyson appeared, decked out in a vintage brown leather coat with sheep fur around the collars and a woolen, pimp-like knit cap. He was swarmed by fans and reporters who stuck pens and business cards and cameras in his face and then asked him aggressive questions, looking to tease a scoop.

"Can you beat Lennox Lewis?"

"What about Roy Jones?"

"Mike, will you fight Klitschko?"

"Yeah," Mr. Tyson laughed in response to the last question. "Tell your promoter to buy me a Ferrari."

Mr. Tyson signed every paper and boxing glove sent his way, and while he did his best to go unnoticed, the mob followed him from the Garden and trudged out with him into the snowy midtown sludge. They asked him to sign more things, they asked him about his future plans—and when the cold wind began whipping down 33rd Street, after nearly half a block or so, the crowd eventually disappeared.

His hands snug in his coats pockets, flecks of gray stubble freckling his chin, Mr. Tyson turned down the corridor that runs beneath the Garden, where the homeless lay their beds in the heated doorways leading to Penn Station. He looked through the windows and saw their sleeping bodies covered in ratty flannel blankets and said simply, "Money."

Mr. Tyson then remembered a time when he came to the Garden as a teen and followed the fighters and trainers from the post-fight press conferences back to their cars—or as far as they would tolerate him. Then, almost spontaneously, Mr. Tyson hollered down the empty corridor.

"Whew!" he yelped. "Man, money can ruin your soul."

You may reach Geoffrey Gray via email at: ggray@observer.com.

This column ran on page 19 in the 12/22/2003 edition of The New York Observer.

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