Fri. Sep 5th, 2025

The moment a 14-year-old Mike Tyson nearly quit in the ring

Editor`s Note: This article is an excerpt from Mark Kriegel`s book `Baddest Man: The Making of Mike Tyson`, detailing the early amateur fights of the future champion at age 14.

Cus D`Amato didn`t attend any of Tyson`s fights until May 27, 1981, at the Catholic Youth Center in Scranton, Pennsylvania. That night, Kevin Rooney would improve his record to 14-0 with a unanimous decision win in the co-main event. But the amateur bouts started the evening, featuring Tyson against a seventeen-year-old from nearby Kingston, across the Susquehanna River. His name was Billy O`Rourke, a senior from Wyoming Valley West High School. Before the fight, D`Amato made sure to find him, sitting alone on the bleachers.

“Billy? I need to speak with you.”

O`Rourke looked up. He didn`t know much about Cus D`Amato, only that he was from New York and resembled Yoda from Star Wars. “You`re a fine-looking young man, a nice kid,” D`Amato began. “I`m sure you have a promising career ahead of you. I just don`t want you running into a buzz saw.” A buzz saw?

“Michael is destined to be champion of the world,” D`Amato stated matter-of-factly. “Champeen of the woild,” in the old man`s distinct accent. “He`s a killer. A monster.” “He`s hurting grown men,” D`Amato continued grimly. “Everyone is scared to fight him. I just want you to be aware so you can be ready. You need to be extremely cautious.”

Soon Tyson arrived. The old man introduced them.

“Hi. How are you doing?” he said softly.

For a killer from Brooklyn, Billy thought, he looked quite ordinary. They weighed about the same, two hundred pounds. However, at six-two, Billy noticed he had about four or five inches on Tyson. And that lisping soprano voice! `There`s no bass in this guy`s voice,` he thought. Forty-two years later, I asked Billy O`Rourke, now a retired correctional officer, why the kind old man was trying to mess with his head.

“He wasn`t,” Billy insists. “He was genuinely trying to warn me.”

A warning like that must have been frightening. I wondered what Billy was thinking as he left to get his hands wrapped.

“I`m like, I`m going to destroy this guy.”

Tyson was officially 4-0 at the time, not counting the smokers at the Apollo. But all his fights had ended much the same way, by knockout, most in the first round. All he knew of O`Rourke was his apparent role in this scenario – the white guy – and, from his deep studies of boxing history, the prejudice against white heavyweights dating back over seventy years to Jack Johnson and the calls from another popular American writer, who urged former champion Jim Jeffries to come out of retirement and avenge the insults Jack Johnson had inflicted upon the white race. “`Jeff, it`s up to you,`” wrote Jack London.

It was a good thing, then, that London wasn`t there for the first round. As it began, Tyson wound up for a big, wide left hook, generating significant power from his torso twist. Billy saw it coming. He knew exactly what to do and firmly readied his right glove by his chin. Boxing 101: He`d catch the hook on his glove, then counter with his own right hand-hook combination.

Billy caught the hook, but it was unlike any other punch he had ever absorbed, before or since: “I blocked the punch, but it went right through my guard. He knocked me flying into the air.”

It`s crazy what you remember on the way down. First, it was the boxing shoes. It took Billy a moment to realize they were his own. Then the blood. There would be a lot of it that night. Then Tyson hit him with another flurry. He would need sixteen stitches to close the cut beneath his right eye. But Billy begged the referee not to stop the fight.

Here`s a side note, explained to me by Teddy Atlas around 1991, shortly after I began writing a sports column for the New York Post: Power is intoxicating, not only for fans but for fighters themselves, whether they are fourteen-year-old boys or heavyweight champions like George Foreman. The real test of a fighter`s character, then, is what happens when they face an opponent who takes their best shot and doesn`t – my favorite Atlas word here – submit. It depends on the fighter, of course. Are they a bully or a professional? A bully`s heart rate will quicken. Their breath becomes shallow. They start to overthink, then doubt themselves. Soon enough, they are imagining their own humiliation. The longer this goes on, the greater the chance they will find a way to quit.

This was undoubtedly a test for a kid already touted as a future heavyweight champion. The outcomes, however, remain open to interpretation, or perhaps, conflicting accounts. Tyson`s version is straightforward enough: an unexpectedly tough fight against “this crazy psycho white boy” who kept getting up. He reasonably remembers the second round as “a war.” Before the third, Atlas reminded him of how he had spoken of being a great fighter, like the legends they had studied on film in the attic: “Now is the time. … Keep jabbing and move your head.” Tyson recalls knocking O`Rourke down twice more. As the fight ended, though, a bloody Billy had him against the ropes and was slugging away. While the fans loved it, D`Amato`s assessment was more measured. “One more round,” he told Tyson, “and he would have worn you down.”

While Atlas`s account makes little mention of D`Amato, it is longer and filled with the kind of fiercely inspiring rhetoric for which Teddy would become known. As in Tyson`s memory, O`Rourke is a mere stereotype, almost an abstract figure: big, unskilled, tough, white. At the end of the first round, after dropping him twice, Tyson returned to the corner and claimed his hand was broken.

Atlas recalls grabbing the hand, squeezing it tightly, and delivering a speech. It began with “The only thing broken is you” and ended with the trainer pushing his fighter back into the ring, after which Tyson knocked O`Rourke down twice more. After the second knockdown, Tyson returned to the corner and declared, “I can`t go on.”

That`s a lot to say to a fourteen-year-old between rounds. Nevertheless, Atlas again lifted him from the stool and sent him out once more. When he saw Tyson was ready to quit again, Atlas got onto the ring apron and urged him to hang on, which, in an apparent miracle, he managed to do.

“It was a defining moment for him, a truly critical point,” Atlas concludes. “Because if he had quit then, he might never have become Mike Tyson.”

Their accounts – Teddy`s and Tyson`s – offer an interesting comparison. Looking back, however, Billy O`Rourke`s seems the most credible. “I`m not calling anyone a liar,” he tells me. “But I was there. I should know. I sparred more than a thousand rounds and had countless fights. I was wobbled a couple of times. But I was only down once in my entire career.”

That single knockdown was in the first round with Tyson at the Catholic Youth Center. What none of them – neither Tyson, Atlas, nor D`Amato – ever seemed to grasp was the caliber of athlete Billy O`Rourke actually was. He had been wrestling since fourth grade and had recently knocked out the fourth-ranked heavyweight in the country. He could run eighteen miles in two and a half hours. Triathlons? No problem. Billy O`Rourke didn`t have a father, but like Tyson, he had a coach who also promised he`d reach the top. But while Tyson was sparring with Lennie Daniels, Billy was already at Deer Lake, Pennsylvania, where Muhammad Ali was preparing for Larry Holmes. He`d sparred with Ali. He`d been in the ring with Tim Witherspoon, who would win the WBC heavyweight title in 1984, and Brownsville`s own, Eddie Mustafa Muhammad, who had just lost his light heavyweight belt to Michael Spinks. “I`ve been hit squarely in the face by Ali and Witherspoon,” he says. “It didn`t really hurt me. But Mike? Mike hurt me.”

In the second round, as Tyson visibly tired, O`Rourke faked a jab and threw his right hand. It was perhaps two inches from landing when Tyson countered with a hook to the body, followed immediately, with the same hand, by an uppercut. This would become one of Tyson`s signature combinations, but O`Rourke remains less impressed by the power than by the sheer speed.

Waiting for the third round, he remembers, “that`s when Teddy Atlas and Mike Tyson were having issues, because Mike didn`t want to fight anymore. He kept saying he hurt his hand. Was it as dramatic as Teddy makes it sound? I didn`t see it that way. I just thought Mike was doubting himself a little.”

When it was over, Tyson whispered in Billy`s ear: “I think you won.” “Did you?” I asked him.

“It was a split decision. Many people from the hometown crowd thought I won. But I was there, Mark. I didn`t win that fight.”


Jesus Carlos Esparza was six when his mother strapped a shoebox over his shoulder and told him to fill it with olives. The family traveled wherever there was work: from Texas to Minnesota, where they cleared weeds for the sugar beet harvest, to California`s Central Valley, where they stooped or reached for whatever was in season: olives, oranges, lemons, peaches, pears, and plums. By age thirteen, Esparza`s strongest desire was for a trophy, and he believed boxing offered his best chance. He was a large, strong kid who ran the three miles to the local gym and back every day. By the summer of 1981, with about fifty fights under his belt, Esparza had qualified for the Junior Olympics. He weighed 215 pounds, possessed a decent jab and a good right hand, and prided himself on hitting hard. Although he was sixteen, his coach lied about his age to enter him in the fifteen-and-under division. This wasn`t much of a favor, as he drew Tyson in the first round: Wednesday, June 24, in Colorado Springs, twenty-seven days after Billy O`Rourke`s fight.

Esparza arrived in Colorado Springs by Greyhound bus nearly a week before the fight. “There was a recreation area,” he remembers, “and all the heavyweights were checking each other out. But when Mike Tyson walked in, we were like, `Holy s—.` He didn`t look like any fourteen-year-old.”

The next day, in the mess hall, he overheard a coach from New Jersey saying only one fighter had ever made it to the second round against Tyson. *Could that even be true?* Esparza wondered.

They all trained in the same gym. Tyson didn`t talk much, wouldn`t make eye contact. But damn, he was ripped. “You lift?” Esparza asked.

“Push-ups,” he mumbled.

They took the fighters up Pikes Peak by train. Esparza recalls the way Tyson`s eyes lit up with wonder. They didn`t have deer in Brownsville.

Esparza remembers Atlas: “Real skinny. But I`ll never forget that scar.”

The night of the fight, Tyson was eating a giant hamburger with a mountain of fries and a large soda. Esparza had always been told never to eat heavily before a fight. He tried to convince himself he had an advantage.

By the time the fight started, though, Tyson had become ferociously animated, coming out with that rapid D`Amato shuffle, gloves held high at his cheeks, head swaying side to side like a pendulum. He wasn`t that hard to hit, though. Esparza landed a couple of jabs. Then a right. Then another.

“I thought they would hurt him,” he says. “But they just seemed to make him angry.”

Then Tyson hit Esparza, landing a jab on his chest. “Knocked me right on my butt,” he says. “I remember getting off the canvas, thinking, `What the hell was that?`”

Esparza tried to fight back, but his straight punches didn`t seem to have much effect. Tyson kept swinging away. Finally, Esparza found himself against the ropes. He saw it coming: a big, looping right hand. He pivoted to block it, perhaps too much. Or maybe Tyson`s reach was long and a little wild. He remembers the blow landing on his back, technically a foul. The referee was on the other side and didn`t see it. But Esparza wasn`t about to say anything. He couldn`t even breathe.

“First time I ever had a fight stopped,” he says. “I`ve never been hit that hard in my life.”

I asked him about Atlas`s credited account in *The Daily Mail* (Catskill, New York): “Thor himself couldn`t have belted out a more blunderous shot.” Atlas claimed it was over in thirty seconds.

“No,” says Esparza, “I almost lasted the whole round.”

Esparza`s single consolation prize from that week in Colorado was this: At least he lasted longer than the other guys. The next opponent was a kid from Texas, possibly 260 pounds. “We were all watching,” says Esparza. “He was in full defensive mode the entire time. I remember him getting absolutely beaten up, and I remember the sound he made when Tyson kept hitting him.”

A high-pitched sound. *Ooh-ooh-ooh-ooh-ooh*. “It lasted forty seconds, I think,” says Esparza.

The fact that there was a rest day before the final round couldn`t have helped Tyson`s next opponent, Joe Cortez from Michigan. Cortez himself had a reputation as a knockout artist. But Esparza saw him change: “He was trying to act really confident. But you could see he was nervous as hell. By then, everyone started telling him, `Oh, s—, you have to fight the monster.` By now, there was a rumor circulating that Tyson was Sonny Liston`s nephew.”

Indeed, he had already mastered the core Liston-esque concept. “Anybody I hurt,” Tyson recalled about his teenage self, “my life gets better.”

Meanwhile, the fighter Cortez had beaten in the semifinals was bragging that he let the kid from Michigan win: “I knew if I won, I`d have to fight that animal Tyson.”

Cortez, for his part, came out swinging, though it wasn`t much of a fight. Tyson was wild and wide. But it was over in about eleven seconds: Cortez sprawled on the canvas, with a doctor and EMT hovering over him. Esparza will never forget the sight. Still, while he was in awe of the Tyson he met in 1981, he has a different perspective on him now.

“I`ve worked with kids who had that same intensity,” says Esparza. “It just grows as they get older.”

Esparza went on to earn a master`s degree in social work from Fresno State. He has worked in group homes, women`s shelters, on Native American reservations, and with Child Protective Services. I`m not exactly sure what kind of rage he means.

“I give Tyson a lot of credit for talking about being molested as a kid,” he says. “I think about some of his interviews over the years and his anger, how he tried to be, you know, really masculine to hide the feelings of what he went through, his past, his memories. It all makes sense, learning his story.”

I`m not sure that offers much comfort to Joe Cortez. Since the Junior Olympics finals were televised on ESPN, then a nascent cable sports network, they have achieved a peculiar sort of immortality, serving as the earliest recorded clip in an endless video archive of Tyson the Destroyer. A Google search reveals several versions that refer to him as “an animal.” These descriptions are not ironic, merely intended as praise, but they obscure what was truly happening. For all the insightful talk about how a fighter should manage fear, this fourteen-year-old boy was internalizing another lesson: how to project his fear, how to use it as a weapon.

“As my career progressed,” Tyson would recall, “and people started praising me for being a savage, I knew that being called an animal was the highest praise I could receive.”

By Gareth Fenton

Gareth Fenton lives and breathes combat sports from his home in Bristol. A passionate journalist with over 15 years covering everything from boxing to MMA, he's known for his incisive analysis and fighter interviews.

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