The Last Great Fight: The Extraordinary Tale of Two Men and How One Fight Changed Their Lives Forever, by Joe Layden (St. Martin’s Press, 320 pp., $24.95)

In February 1990, a few days after Mike Tyson lost the heavyweight championship to James “Buster” Douglas in Tokyo, Sports Illustrated showed the fallen boxer on its cover and ran a photo spread and report inside. In the days before the Internet, such a production was eagerly awaited. Paging through the magazine on a commuter train, I was interrupted by a man seated behind me, who asked, “Do you mind if I just look over your shoulder?” Soon a small crowd of men had gathered around, doing the same.

That’s the kind of allure Mike Tyson had from the very beginning, and certainly in 1990, when he lost to Douglas in a monumental sports upset that few had seen coming. Tyson was only 23 years old; he was undefeated in 37 fights; all but a few of his wins came by knockout, most of those in the early rounds, sometimes in the first few minutes or even seconds. He was expected to have a long reign as champion and take his place in the pantheon of boxing greats like Joe Louis and Muhammad Ali, and others whose names were less known to casual fans, but whose deeds Tyson had studied for years in old black and white films. Most of his opponents came into the ring already beaten mentally, looking for a place to fall. Tyson was a fixture in the pop culture, a character in video games and commercials, a frequent presence on magazine covers, and—of late—in tabloids, as his life slowly unraveled into a circus sideshow.

Joe Layden’s The Last Great Fight tells the story of Tyson and Douglas and that memorable evening in Tokyo when the impossible—but now, in retrospect, the inevitable—happened. If his title is a bit of hyperbole—there have been great fights since, even if few of us have seen them—he’s certainly right in his larger point: Tyson’s defeat that night was really the beginning of the end of boxing’s last period of glamour. Without a heavyweight champion who captures public imagination, boxing is the sporting equivalent of a political third party: you’re always a bit surprised when someone you know is involved with such weirdness. Peopled with gamblers and ruthless, amoral promoters like Don King, the sport’s action involves two grown men apparently trying to do nothing more elevated than beat one another into submission. But Layden understands what boxing commentators like Larry Merchant and Jim Lampley, who were ringside in Tokyo, know from years of calling fights, and what innumerable boxing writers and fans, too, have learned through their own devotion to the sport: that its dangerous, primitive theater is rich in character and pathos, drama and lore, in a way that no other athletic competition can match. When boxing reaches its rare pinnacles, as it did in Tyson-Douglas, it can seem to a fan like the only thing worth paying attention to.

Though the basic narrative of the Tokyo fight is familiar, Layden fills it in with fascinating and little-known detail, the product of interviews with fighters, trainers, the HBO commentators, and other boxing insiders. We learn that Tyson’s deservedly maligned cornermen—who lacked even rudimentary equipment to help their fighter on what became his most desperate night—were at least competent enough to worry about the champion’s lack of interest in the Douglas bout. Tyson’s lead trainer, Aaron Snowell, presciently told him that he was in real trouble if he didn’t start getting serious in training. Tyson shrugged and responded with an odd sentiment for an unbeaten and seemingly indestructible fighter: “If I get my butt whipped, I’ll take the blame.” Once in Tokyo, Snowell and others in the Tyson camp went out for some early morning roadwork—without Tyson himself!—and came upon a solitary runner up ahead: Douglas. “Let’s see what he’s got,” Snowell thought to himself, and he and his group picked up their pace, moving in on the challenger. Hearing their footsteps, and never once looking back, Douglas shifted into another gear and left the Tyson camp far behind. It was then that Snowell knew that Douglas was in superb condition, and his worries deepened.

Douglas was a talented athlete who never seemed adequately motivated as a boxer, and his career until Tokyo was notable mostly for squandered potential. But after the death of his mother, with whom he was close, he came to Tokyo a different, much more determined, man. Layden draws a picture of a complex character, with a wry sense of humor and a son’s universal burden: he could never seem to please his volatile, intense father, a respected former light heavyweight contender who was not known for “leaving his fight in the gym,” the way his son sometimes was. “I wish I could fight this guy,” Bill Douglas told his son by telephone on the eve of the bout. Yet it was Douglas’s affectionate, kind-hearted mother who ultimately inspired him. Not long before she died, he visited her in the hospital and noticed that she was reading a biography of Tyson. Naturally, she was terrified. But Douglas, in one of the book’s best moments, tells her: “Mama, I ain’t worried about that punk! I’m a killer!”

Douglas just about lived up to his boast. Layden’s round-by-round coverage of the fight is engrossing, almost enough to make the reader suspend his knowledge of the outcome and anticipate the ending anew. Douglas dominated the fight from the opening bell, using his superior size and reach to keep Tyson off him and repeatedly tattooing the baffled champion with his left jab and combinations. (Layden’s vivid account reminded me that when I watched the fight live on HBO, Tyson seemed to become smaller with each passing round.) Yet Layden also gives proper due to Tyson’s courage, often dismissed by his many detractors. At the end of his career, he did seem to stop trying, but in Tokyo he was struggling desperately to hold onto his cherished title.

He nearly succeeded. Just before the end of the eighth round, in the midst of another going-over from Douglas, Tyson suddenly set himself and landed a thunderous uppercut that dropped Douglas on his back. Here it was, most observers thought: nice try, Buster. Douglas perched himself up on his elbow, patiently—perhaps a little too patiently—taking the referee’s count, and rising just a hair’s-breath before “10.” (A post-fight controversy centered on whether Douglas had received a “long count,” not the first time a heavyweight title bout had become embroiled in such a dispute.)

Just as Tyson crossed the ring to finish off Douglas, the bell rang, ending the round. Tyson tried to follow up in the next round, but his eyes were closing from the battering he’d taken, and he had little left. Douglas landed a thunderous uppercut of his own in Round Ten, sending Tyson crashing to the canvas in a heap, where he then proceeded to enact one of those hypnotic sequences boxing sometimes produces: on his hands and knees while the referee tolled the seconds, Tyson did not rise immediately but instead—“like a man in search of a lost contact lens,” as Layden puts it—fumbled to retrieve his mouthpiece, finally putting it in his mouth backward and haltingly getting to his feet as he was counted out. Then he collapsed into the referee’s embrace—suddenly a deeply pitiable figure, where less than an hour earlier he was the self-proclaimed Baddest Man on the Planet.

Layden’s coda continues to follow both fighters. Douglas was almost immediately engulfed in all-too-predictable managerial struggles for control of his career, now that he was a hot property, and was bewildered by the new demands and expectations. He lost the title in his next fight, retired, and in short order ballooned to nearly 400 pounds, nearly dying in a diabetic coma. Eventually, he shook himself out of this personal despair, regained his health, and seems reasonably content today. As for Tyson, well . . . as Layden puts it, his life since Tokyo has been a “tragedy with a laugh track.”

Inevitably, Tyson’s long shadow lies over the book. Layden is sympathetic, if unsparing, in describing Tyson’s many failings and eventual depravities. He shows us enough of the young Tyson, the dynamo fighter and the young kid with more than a hint of sweetness inside and aspiration to overcome his harsh origins, to make us lament his eventual fate. Indeed, Tyson has traveled a long and depressing road, from “What round did I stop the gentleman in, anyway?”—a question he asked early in his career—to “I’m on the Zoloft to keep from killing y’all,” as he said a few years ago. Joe Layden’s fine book depicts the Tokyo fight as the fork in that road, the point at which Tyson’s descent began. Whether that’s true or not, the fighter agrees with the assessment. “My career’s over,” he tells the author in their one conversation. “It’s been over since 1990.” What a career it was, and could have been.

Paul Beston is associate editor of City Journal.