His Literary Heroes & the Fight for Legacy

Gifts are never easy. But what do you give a man like Mike Tyson? He’s been a champion, an outcast, an inmate, an addict, an actor, an icon. Plus, boxers in training are notoriously hard to please. As the date of the bout gets closer, they get edgier with nerves, clinging to their routines and superstitions. And yet, there I was this past summer, packing my bags, heading off to interview him at his training camp in Las Vegas, searching for that curio, that token, something a bit more meaningful than a keychain or an overpriced neck pillow from the airport.

Yes, that’s right. In case you missed the news, Mike Tyson is fighting again. On November 15, he’ll step back into the ring, this time to face Jake Paul, the internet curiosity and aspiring boxer. The bout—eight rounds, two minutes each—will take place inside the massive AT&T Stadium, home of the Dallas Cowboys, and be streamed live on Netflix. When you add up the streamer’s 283 million subscribers, the 100,000 people at the Dallas stadium, and the gazillions of people around the world watching online, the fight is set to be among the biggest sports spectacles of the year. For Tyson, now 58, a win would be the perfect way to end his historic career on a high note, after losing so much time to scandals and drug addiction. For Paul, 27, it would be the chance to emerge into the land of legitimacy, to transform from YouTube prankster to respected athlete, especially after handpicking so many inferior opponents.

The themes are clear. It’s a battle between the old master and the cocky upstart, a clash of refined skill against raw, crude ambition. Paul is the heavy favorite, Tyson a four-to-one underdog (at the time of reporting). “Edge-of-your-seat shit,” as a boxing friend puts it.

Back to the gift for Tyson. We first met more than 20 years ago, when I was covering the boxing beat for the New York Times. Throughout the years, hanging out and talking with him at his various fight camps, I’ve come to learn one thing about Tyson that many don’t get to see: He’s a history nerd.

“History is interesting,” he told me. “You know, it helps us discover who we are. What the fuck am I? How am I here? What? We always try to figure ourselves out.”

Tyson, the dropout, the kid from the streets, discovered the classics not in school but in the house of his legendary trainer, Cus D’Amato. D’Amato’s library was Tyson’s refuge—a place where tomes by Darwin, Tolstoy, Machiavelli, and Wilde sat waiting to be discovered. Tyson devoured them all. “I wasn’t interested in school,” he confesses in Undisputed Truth, one of his memoirs. “But I did have an urge to learn,” he writes. “By reading history, I learned about human nature. I learned the hearts of men.”

There’s something poetic about Tyson’s education—the way it unfolded not in classrooms but in the quiet corners of D’Amato’s home, where the ghosts of philosophers and warriors seemed to speak directly to him. An early serious study was Zen in the Art of Archery, a book that had found its way into D’Amato’s hands courtesy of Norman Mailer, a friend and frequent visitor to D’Amato’s home. When Tyson was in his early teens, D’Amato read the book aloud to him, introducing him to the idea that true mastery comes not from technique alone but from something deeper, something in the subconscious. And, as if channeling the mystics themselves, D’Amato took things further. He led Tyson to a hypnotherapist, who taught the young man to lie on the floor while his mentor towered over him, chanting words of destiny:

You’re the world’s greatest fighter.…

You are a scourge from God. The world will know your name from now until the eons of oblivion.

Perhaps it was inevitable then that Tyson, a participant in D’Amato’s strange rituals, would see himself as larger than life and tasked with the weight of becoming a kind of pugilistic god.

A young Mike Tyson and his trainer, Cus D’Amato, who sparked his love of literature.

By the time he was 15, the aspiring boxer was deep into Nietzsche’s writings, convinced he was the Übermensch. “I could barely spell my name but I was Superman.”

There was a warrior lineage, he was told, consisting of famous conquerors throughout the ages, brave men like Alexander the Great. “I studied him,” Tyson told me. “His whole prime. He’s been glorious. He conquered the world at 20. I conquered the world at 20 [by becoming the youngest heavyweight champ]. And I used to feel a great kinship with him.”

But it wasn’t just the ancients who filled his thoughts. Tyson became obsessed with the tactics and techniques of former champions, the great boxers who had come before him. He studied their films, their records, their lives. He learned their punches, their quirks, their habits. “In order to reign, you have to serve,” he told me. He served by studying. In doing so, he uncovered the hidden treasures of intellect and artistry behind the brutality of the prize ring, from the ballads of the bare-knuckle days to tales of the writer-pug duos in the modern era. George Bernard Shaw and Gene Tunney. Langston Hughes and Joe Louis. James Baldwin and Floyd Patterson. (In keeping with this tradition, Joyce Carol Oates befriended and wrote about Tyson).

Tyson’s obsession with history and literature led to a kind of isolation. While his peers in high school were out enjoying their youth, Tyson was bent over books about dead champions and their ghosts. “Cus would urge me to go out dancing or something,” he writes, “but I would rather curl up with a book about Benny Leonard.”

That’s how we met. Benny Leonard. The Ghetto Wizard, they called him. He was a scrappy little Jewish kid who grew up learning to fight bullies on the Lower East Side and, in the 1910s and ’20s, went on to become arguably the greatest lightweight champ in boxing history. He’d gone undefeated for almost eight years, one of the most celebrated accomplishments in sports. He was an inspirational figure in New York then, uniting the impoverished Russian Jews of the pushcart-peddling Lower East Side with the wealthier and more assimilated German Jews uptown. Arthur Brisbane, the legendary Hearst newspaper editor, wrote that, as one of the first Jewish boxing champs, Leonard “has done more to conquer anti-Semitism than a thousand textbooks.”

Twenty-four years ago, when I was living on the Lower East Side and covering boxing, I was planning to write a book about Leonard. For research, I collected old newspaper clips about his life and times and was able to get VHS tapes of his biggest fights. As a writer, I found the sport irresistible—the characters, the culture, the tension. I started covering a few fights for the Times, hanging around the gyms and following up-and-comers. That’s how I met Pete Pharaoh.

Pharaoh worked as a conductor on the Long Island Railroad. I recall that he sometimes took pictures of fighters in New York. He also, he told me one night, had a social connection with Luz Whitney, a model who was dating Tyson.

“I just spoke to her,” he said casually. “She’s with him right now.”

At the time, Tyson was a phantom. He’d been the youngest heavyweight champion in history, but after D’Amato’s death, his career veered off course. A rape conviction in 1992, a crime he still denies, sent him to prison, and later, his struggles with drugs derailed any chance at a proper comeback. He was impossible to reach and avoided the press.

I asked Pharaoh to put me in touch.

“He’s staying at the Beverly Wilshire in L.A.,” Pharaoh said, under the name Arnold Rothstein.

Arnold Rothstein? The man who fixed the World Series? F. Scott Fitzgerald’s inspiration for Meyer Wolfsheim in The Great Gatsby? What was Tyson doing using the alias of a Jewish criminal mastermind from the Roaring Twenties?

That night, once I got home from a weekend bout at the Amazura Concert Hall, in Jamaica, Queens, out near John F. Kennedy International Airport, I called the front desk at the Beverly Wilshire hotel. Through the phone, I could almost smell the gardenias, feel the cold Italian-marble floors—whatever luxury props the hotel used to decorate its lobby. I had no idea; I’d never been there. I was just a cub reporter calling from a shared apartment in a grimy, walk-up tenement.

“How may I help you?” the receptionist asked.

“Mr. Arnold Rothstein, please?” I said, trying not to laugh because the real Arnold Rothstein had been dead for three-quarters of a century.

“One moment. Let me put you through,” she replied.

As the phone rang on and on, I couldn’t help but doubt it all.

“Would you like to leave a message?” the receptionist asked, and I passed on a note that only a Rothstein trivia buff would appreciate. From my Benny Leonard research, I knew that Rothstein got his start in the billiard halls of the Lower East Side. The message went like this: “Before the big time, what was the big A.R.’s claim to fame?”

“And who may I say this is from?” the receptionist asked.

“Benny Leonard,” I said, and then went to sleep, chalking it up to a wild-goose chase.

At around 4 a.m., my phone rang, jolting me awake. It was Tyson.

“My brother, who the fuck are you?” he said. It was one in the morning his time, and he was fired up, riffing about Rothstein and the gambler’s connection to the lightweight title fight in the summer of 1922, held at Boyle’s Thirty Acres in Jersey City, New Jersey, with Leonard facing off against Lew Tendler, a southpaw from Philadelphia.

“That must have been off the hook!” Tyson went on, theorizing that Max “Boo Boo” Hoff, a Philly underworld boss, was behind Tendler, while Rothstein was backing Leonard.

“I would have loved to have been there!” Tyson said.

The sun was rising as we spoke, and a few months later, I was on my way to meet him at his training camp in Phoenix. Tyson was tuning himself up in the hope of securing another title fight, and channeling yet another historic figure, only this time from the pages of 19th-century French literature.

The gym was in downtown Phoenix. I remember the faded boxing posters peeling off the walls, the dry, choking heat pressing in from every crack in the dirt-caked windows. Tyson was in a dark place then, consumed by drug addiction, lawsuits, bankruptcy, and other factors that had stripped away the approximately $400 million he had earned throughout his career.

“I’m the Edmond Dantès of boxing,” he told me in the gym’s locker room, referring to the protagonist of The Count of Monte Cristo, which he revealed was among his favorite books. He’d immersed himself in this and other works by French writer Alexandre Dumas during his time in prison.

The Count of Monte Cristo by Alexandre Dumas is among Tyson’s favorite books.

“Best three years of my life,” Tyson said about his incarceration. Without the relentless pressure of fame, he found his time behind bars liberating. He exercised daily, learned Chinese, and read. His cellmate Farid (formerly known as David Barnes) was an active reader too. They tackled many of the great works of literature, reading passages aloud; shared a thesaurus and a dictionary; and mastered new words by using them in sentences.

“I gravitated to reading rebellious, revolutionary books,” Tyson writes of this period in Undisputed Truth. “I read Mao’s book.… I was right there next to Mao on that long fucking march.” He goes on: “I read Che. I read Machiavelli, Tolstoy, Dostoevsky, Marx, Shakespeare, you name it.” Hemingway, however, didn’t quite land for him. “Too much of a downer.”

But out of all the authors Tyson devoured in his cell, Dumas shone.

“Whenever I felt lost in prison, I’d read some Dumas,” he writes. “I really identified with the main character Edmond Dantes [sic]. He had been framed by his enemies and sent to jail too. But he didn’t just sit there and brood; he prepared for his eventual success and revenge.”

At the Phoenix training camp, Tyson was looking to rebound from hitting rock bottom. “My life has been a total waste,” he told me then. “I don’t have nothing; I don’t have nobody.” He considered himself the loneliest person in the world, forced to start his career from scratch, organize his life, and make an outsider’s bid to reclaim the championship. Just like in prison, he was turning to Dumas’s Edmond Dantès for hope.

“Don’t rob me of my hate,” he told me, quoting a favorite line spoken by the lead in the 2002 movie version of Dumas’s novel. “It’s all I have left.”

Despite underperforming in his last two pro fights nearly two decades ago, Tyson made a spectacular return during the pandemic, taking on Roy Jones Jr. in a much-hyped exhibition bout. At age 54, he had teamed up with a new trainer, appeared in incredible shape, and outperformed the critics’ expectations, resulting in a controversial draw.

We’re now a week away from the Paul fight. Already, it has been postponed once, after an ulcer flare-up on an airplane sent Tyson to the hospital, derailing his training camp. He’s also closing in on 60, nearly three decades older than the usual retirement age for former world champions. But despite his years, his scores of fights, and the intense partying of his drug-fueled days, he looks great on videos leaked by his camp, attacking the punch mitts with terrifying speed and power.

He’s also back on top financially, having started a few businesses with Kiki Tyson, his wife of the past 15 years and whom he credits with keeping him sober, in shape, and inspired. Together, they own a cannabis company, a clothing line, a gym, and other enterprises.

Kiki is big into wellness, and Tyson forgoes coffee and candy and hums along in a kind of happiness groove (with the help of cannabis and psychedelics). He can often be spotted in the stands of tennis tournaments, as Milan, the couple’s 16-year-old daughter, is looking to turn pro and has been training in France with Patrick Mouratoglou, Serena Williams’s former coach. Their son, Morocco, is following suit, playing golf and running track. Tyson has four other children, most of whom are in college and seem to be doing well.

All of which brings me back to my visit with Tyson at his Vegas training camp and that gift. What do you get for a man who doesn’t actually need anything?

A history book? Too obvious. A bottle of high-end añejo tequila? Not for a man in recovery. But then, rummaging through a sock drawer, I found it. An old VHS tape, tucked away, from my boxing reporting days. It featured the person with whom this story started. I packed it in my suitcase. The title: Benny Leonard on Film.

Seven Hills is one of those exclusive communities outside of Las Vegas where you’d expect to find famous actors and performers living behind towering gates. The Tyson family resides here in a sprawling five-bedroom, 10,000-square-foot mansion; there’s also Tyson’s prized pigeon coop: the home of his South African distance rollers, a breed known for its aerial flips. The house was under renovation, so after talking at the gym and sipping on tea, Tyson and I retreated to a room off the garage to watch old Benny.

Tyson looked exhausted, having been up early to train (“Gotta beat the sun”), and as we waited for Farid—released from prison and now his executive assistant—to find a VCR, the conversation drifted.

“Benny Leonard had balls, you know what I mean?” Tyson said. “He wasn’t afraid. He’d stand up for himself.”

In 1932, Benny Leonard attempted a comeback after having retired over six years earlier. He was defeated by a younger opponent.

Tyson leaned forward, the fatigue momentarily fading. “The reason I’m a Benny fan is ’cause he got fucked up in his first fight. He didn’t do good. Then he won a fight, then another. And then he didn’t lose for seven and a half years. That’s the mind, once you get confident.”

I asked him about Rothstein, about using the guise so long ago. What was his attraction to the famous gambler?

“He was just a big, egotistical guy,” Tyson said. “He reminded me a lot of Cus. He believed so totally in what he thought. He thought he was the smartest guy in the world.”

I asked Tyson what historical period he’d like to return to.

“I’d probably go back to biblical times, like 300 to 500 BC,” he said, marveling at the early customs of daily life. “I want to see how that shit worked.”

We talked about his favorite places to travel, like Russia, home to another of his favorite writers, Leo Tolstoy.

“Tolstoy runs circles around these guys,” Tyson said, referring to modern novelists. He admired that Tolstoy came from wealth but rejected it.

“He was a count, royalty,” he said. “His family were capitalists. He wasn’t. He became a Communist. The big thing between him and his wife? She wanted to sell his books. He wanted to give them away for free.”

Soon enough, Farid returned with a VCR. After some fiddling with cords and jacks, the black-and-white images flickered to life—the heroes of the 1920s appearing before us silently, as if time itself had blurred. The robes were bigger then, the stands filled with fans in derbies, and there was Leonard, light on his feet, dancing around the ring. We watched the first Tendler fight, the rematch, then Leonard’s comeback against Jimmy McLarnin in 1932, where, against the younger, nimble opposition, the older Leonard got pummeled.

“I used to talk to him from prison,” Tyson said, speaking of McLarnin, just one of many fighters Tyson has had a connection with, even across generations.

An hour passed, then another. After the McLarnin fight, toward the end of the tape, boxing gave way to a silent feature film. We watched Leonard run through the forest in knickers and a white sweater, looking debonair, almost carefree. The old footage felt like a glimpse into another world—one Tyson had admired since he was a teenager. But as much fun as it was to look at, I felt like I had taken enough of his time. It was nearly 11 at night.

“You’d better get some rest, champ,” I told him, rising to stop the machine. I figured he’d want to hit the sack, to be up and training early the next morning. His match with Paul—a younger, nimble, and hard-hitting opponent—would be here soon.

But Tyson wasn’t having it. His eyes stayed glued to the film. “No,” he said, his voice low but firm. “I love this shit.”

And at that moment, I understood. The VHS tape of old Benny Leonard that I had brought from my sock drawer was not just a gift—it was a mirror, reflecting the fight Tyson was still having with himself, with time, with his own legacy. Or perhaps it was a portal, a chance to reconnect with one of the greats he had worshipped since childhood. Watching Leonard wasn’t just a look back; it was a way of paying respect, like sitting in the pews of a sacred hall and lighting a candle for a saint. But it was also a look forward, a prayer for the strength and will to carry Tyson through one more fight and, hopefully, to one last victory.•

Geoffrey Gray is a New York Times bestselling author, longtime investigative reporter, and the current founder and publisher of True Mastery, which specializes in adventure tales and interactive, real-life games. Known for his eclectic range of subjects and gonzo spirit, Gray started his writing career covering boxing for the New York Times and later specialized in unsolved crime, travel, food writing, and more as a contributing editor at New York magazine. He has also produced two feature documentary films, Patrolman P. and GORED, the latter of which premiered at the Tribeca Film Festival and debuted on Netflix. He is the co-creator of 9 Arches, an adventure card game, lives (most of the time) in the colonial highlands outside Mexico City, and once drove an ice cream truck.