Real One: Randall Bailey and a Life Lived Fighting

Randall Bailey knocks out Mike Jones in the eleventh round of their fight for the vacant IBF welterweight world title at the MGM Grand Arena in Las Vegas on June 9, 2012. (Joe Klamar/AFP/Getty Images)

“Workin’, drivin’ trucks.”

That’s how one of the greatest punchers of the past twenty-five years provides for his family now. And he couldn’t be happier. Randall Bailey doesn’t miss boxing.

“You have no idea what it’s like having to deal with people in the boxing business,” he says. Bailey is relaxed, cool, engaging. But when he touches on the underbelly of his former trade fatigue creeps in, he turns stern, as if addressing the leviathan of his past directly. “I didn’t have the right mind, I’d probably be in jail right now instead of home with my family. When you see people stealin’ and takin’ money from you, and you know what you’re capable of doing and what you can’t do . . . ”

He lets this sentence hang for a moment, never comes back to it. Bailey had to get out before people he couldn’t trust could dictate how he fed his family. So he walked away.

His career was over before his final fight; Bailey dates its end as June 6, 2012, the night he beat Mike Jones for the IBF welterweight title. As Bailey understands it, had Jones won he would have been in line for a Pacquiao fight. With the upset, Bailey thought he won the Pacquiao sweepstakes.

That’s logical. Boxing doesn’t work that way.

A mutual friend reached out to Bob Arum about making Pacquiao–Bailey. “If you would’a heard the phone call,” chuckles Bailey, “[Arum] wanted to get off the phone so damn fast. And he was enraged.” Why the hostility? “Because of what happened with Mike Jones,” says Bailey, “After what happened that night, I was never gonna fight another Top Rank fighter.”

That’s why Bailey believes two careers ended that night. Jones fought once more and was knocked out. And Bailey wasn’t getting near another Top Rank fighter—not at his age, not with his power. He had one fight left with Lou DiBella, who “sold me down the drain to Al [Haymon].” In his next fight, Bailey lost a decision to Devon Alexander. Alexander was “nowhere in the picture for a title shot” but he called Bailey out, and so Bailey had to respond.

These are the experiences Bailey is glad to leave behind him.


Boxing wasn’t always forked tongues and fangs for Bailey, though. He loves fighting and always has.

“I used to get in a lot of street fights,” he recalls. “So [boxing] was just me trying to find a way to fight without getting in trouble.” For many, fighting is itself a form of trouble, but on the streets of Bailey’s youth if you beat someone up they might shoot you in return. Sanctioned violence gave young Bailey a security absent from the shadows beyond the streetlights.

After innumerable strolls past the 27th Avenue Boxing Center in Miami, Florida, a curious Bailey finally crossed the threshold into that mysterious world of sweat and leather. “I was fourteen. I never looked back.”

His talent was obvious. “My first trainer, Mr. Grady, told me I was gonna be a world champion my first day at the gym.” But it was another fighter, lightweight Freddie Pendleton, himself training out of the 27th Avenue Boxing Center, who set Bailey on the path to the paid ranks.

Bailey brought a dilettante approach to his amateur career. A natural, he never really trained. A week or so before an amateur fight Bailey would start training, yet even with these lax habits he knocked out half of his opponents. “I used to still be runnin’ around the streets a lot, but Freddie’d tell me ‘Whenever you’re ready to get serious, you let me know.’” Bailey had to get serious when he started getting into serious trouble, when “everything that was going on was leading him back to the gym,” back to its safety. A year later, at twenty-one, he turned pro.


Pendleton baptized Bailey into the pro game. He was merciless. Why? To ensure Bailey would commit fully to his trade. Bailey laughs thinking about that initiation. “Every day I’d leave the gym with two black eyes! We sparred Monday, Wednesday, and Friday. On Monday I got a black eye, if it was goin’ away by Wednesday I got two more. So, by the weekend, I was all black-eyed up!” He thanks Pendleton and those black eyes for making Bailey vicious, “so vicious that when I got in the ring to fight guys who weren’t on that level . . .” He lets this sentence hang too, perhaps remembering how his first twenty-one opponents fared, how they suffered for Pendleton’s bruising instruction.

His respect for Pendleton is tangible; so too is Bailey’s appreciation for the process of becoming a better fighter, for what made him. “But all this is from before the money started coming in. When the money starts coming into the picture, then you have to watch everybody. Everybody wants something.”


Bailey, who retired in 2016 with a record of 46-9 with 39 knockouts, isn’t bitter so much as wizened, accepting but undeceived. And if he could impart some of that wisdom on his fourteen-year-old or twenty-one-year-old self what advice would he offer?

“Go to school. Study hard.”

What about boxing?

“Forget it. I mean, boxing is, is . . . boxing is worse than being a drug dealer. Because I mean, when you’re in the street you know who to look out for. When you’re in boxing you don’t know who to look out for. And the person standing right next to you is probably gonna be the one to stab you in the back.” He has come to this point before, the idea that in boxing, when the money starts to come in, you don’t know who your friends are and so you don’t really know who your enemies are either.

Would the twenty-one-year-old Bailey have been receptive to such a message? Perhaps, but he wouldn’t have sought it. He never would’ve approached another fighter for a picture, let alone advice. Celebrity has never appealed to Bailey, who abandoned Twitter years ago, whose Instagram is private. When he was younger he passed up opportunities to hang out at Don King’s house, to meet Mike Tyson. He trained at the same gym as Evander Holyfield when Holyfield was preparing for Michael Moorer and didn’t so much as shake his hand. “And I liked him!” laughs Bailey, acknowledging how odd this ambivalence might seem.

Years later, Bailey admits this refusal to network and self-promote kept boxing’s power brokers from treating him like a star. Stars don’t pick up people from the airport for Don King, they don’t drive people in town for King’s cards to their hotels. But Bailey would. He didn’t act like a star because Bailey doesn’t act. His honesty may have worked against him in a business based on lying. He doesn’t care. Randall Bailey is a real one.


He had a real career too, replete with peaks, valleys, setbacks, and comebacks. And he’s proud of it, it excites him to speak about how he responded to the tribulations of his career. “Yeah! You see what you said right there,” referring to a career without the powerbrokers’ imprimatur, “that’s where I always was in my career. If I lost a fight, that just drove me to come back harder.” Losses to Diobelys Hurtado, Demarcus Corley, Ishe Smith, Miguel Cotto, Juan Urango, took Bailey away from television cameras, out of the collective consciousness of the sport. It was here that he set his chin and ground out a living, the “KO King” cutting down one man after another in pursuit of the throne.

Late in his career, when he could no longer make welterweight, Bailey came to fully understand how boxing could conspire against him. He reached out to people, looking for junior-middleweight opponents. “We’re not gonna put you in with this guy or that guy,” they’d tell him, or “We wanna use you but so-and-so won’t fight you.” Used to taking challenges, Bailey was dumbstruck by the avoidance. I’m like, ‘Y’all let guys choose who they fight, man?’ They were actually bringing in guys that know they’re gonna lose!”

Still animated—imagine him shifting forward in his chair, gesturing with his hands for emphasis—Bailey continues. “Let me tell you somethin’—when I was comin’ up, I would see my opponents go up to the matchmaker and say ‘Thank you so much for this win.’ Opponents that was comin’ to fight me! And I had all knockouts! But they were thankin’ the matchmaker for puttin’ ‘em in with me because I was untested. And this was their comeback; this was their get back.” He relaxes a bit here, relishing the sentence to follow. “It wasn’t what they thought it was gonna be.”

Bailey isn’t criticizing those opponents, however; he’s celebrating them for their winning mindset. “They didn’t come to lay down like these guys do today. They bring in guys today who come to lay down. This is some new stuff going on.” Perhaps there is some nostalgia at work here, fighters today still turn in inspired and defiant performances. But then you realize his words come almost a year after Mikey Garcia’s feeble challenge of Errol Spence, only two months since Andy Ruiz ate himself out of relevance after turning the heavyweight division on its ear, and you understand why a man who fought for his opportunities might be intolerant of those who squander theirs.


So what went wrong? “I can’t really put my finger on it, but when you start asking for multimillion-dollar fights—you gotta fight!” Bailey thinks that so many people profiting from overpriced fights and the disparity between risk and reward are disincentivizing. So what happens to risky fights like Terence Crawford–Errol Spence? “They ain’t makin’ ’em.”

To expand on his point, Bailey turns to Felix Trinidad. Trinidad is a rare commodity for Bailey, a member of his fraternity that he sought for guidance and insight and one of the greatest, most ambitious fighters of this century. Is Trinidad a fair standard? Bailey isn’t concerned with fairness: Trinidad is an exemplar, his conduct instructive. For Bailey, Trinidad brought the proper mindset to a blood sport: “Y’all say y’all the best? We have to see. We gotta see. There ain’t gonna be no runnin’ round people sayin’ they got the best fighter—we gotta see! Who today would put their Trinidad in with a guy like [Yori Boy] Campas? In his twenties? They ain’t doin’ that today.” He pauses, “Boxing ain’t boxing no mo’, man.”

Unsurprisingly, Bailey doesn’t follow boxing much. He’ll tune in for Canelo Alvarez, tune in for Crawford, but even the Deontay Wilder–Tyson Fury rematch left Bailey cold. He has no interest in returning to boxing in any capacity, not as a trainer, and definitely not as a manager. “I would beat up my fighters. I would beat up my fighters.” Bailey often doubles his responses, perhaps to accommodate for lags in the phone connection, but it feels like this repetition is in the service of clarity, a sort of echo to drive his more emphatic points home. “Because I know what fighters do—I know what fighters do! Fighters are always fuckin’ up!” he laughs. “And I’m puttin’ my money on you? I can see it now: ‘Manager drags fighter out of the club and beats him up. Fighter can’t fight.’”

He isn’t getting back in the ring either. “I posted something on Facebook about me having a farewell fight in Miami. Everybody jumped on it. They wanna see me go out with one last fight.” So what’s stopping him? The same thing that drove him from boxing the first time. “I wanna do it but I would have to deal with certain people and, you know, ehhhh . . .”

Besides, while Bailey was stopped in his last fight by Jeff Horn, he’ll always have his victory over Jones, and no win could ever top that one.


The proliferation of titles is cited as one of boxing’s fundamental flaws; the absence of a single champion in each division seen as proof of a fractured sport, one that broken as it is, is hard for outsiders to grasp. And there’s some truth to that. What’s more, this proliferation promotes what Carlos Acevedo calls “the pursuit of folly,” false promises that encourage fighters to chase dreams they are dangerously incapable of realizing. But what is often overlooked in criticizing boxing’s championship claw crane game is what the titles mean to the fighters. To dismiss as meaningless or trivial something a fighter gives everything for feels wrong. And Bailey’s win over Jones is a case study in why.

“I wanted this so bad—worse than any fight I ever wanted. This was for me. Because, you know, I hadn’t been champion since 2002. And everything that could go wrong went wrong. I had to sit back and like,” Bailey pauses here, not so much to search for the words so much as to confront once again the enormity of the challenge he faced, “just believe in God. I didn’t have nothin’ else.”

Bailey then describes the worst training camp of his career. His trainer, John David Jackson, was invested fully in Sergey Kovalev. “We had all these drills, all these drills I would ask John to do with me, and he’d say, ‘Uh, go hit the bag.’ Like, you’re not even watchin’ me? I could be over here just bullshittin’.”

(Incidentally, it wasn’t the first time Jackson let Bailey down. For both of his fights in Belgium, first against Jackson Bonsu and then against Said Ouali, Bailey ostensibly trained himself. For the Bonsu fight, Jackson left to train Bernard Hopkins, who was preparing for a rematch with Roy Jones Jr., and while Bailey was getting ready for Ouali, Jackson devoted his time to “a slew of Russian fighters.” Bailey recognized he was being used primarily as a sparring partner. Only a few of the fighters he was put in with were his weight and none of them were southpaws like Ouali.)

So, with the help of cutman Chico Rivas, Bailey packed up his gear and brought it home. Rivas would come to his house to help him with strength and conditioning. Bailey tortured himself physically in preparation for Jones but the only time he had any interaction with Jackson was on sparring days. During the fight, Bailey says Rivas can be seen taking control of the corner in the middle rounds.

Still, even without Jackson, Bailey knew he could beat Jones: “I knew when I hit him—I was gonna crush him.” A puncher speaking about power, about its potential for emergency, Bailey’s speech is crisp here, free of much of the syrupy drawl that sweetens his delivery. “I told everybody I was gonna knock him out. And when I saw the odds [Bailey was +400] I told everyone ‘gimme your money, gimme your money.’ My manager went home with almost $50,000 from people that gave him their money to bring to Vegas. Everybody bet on me. I told everyone I was gonna knock him out.”

But these moments of supreme confidence were fragile, under assault. Bailey’s training camp was still “so bad that I would break out cryin’, ‘Why is this happening now? Why can’t I get what I need to be successful in a fight I know I can win?’”

Faith got him through. He prayed, and God told him that so long as Bailey did as he was told God would handle the rest. So what did Bailey have to do? “God takes away the things you feel you can’t live without. My thing was sex—I would not stop. This was my Achilles heel right here. So I stopped having sex, stopped dealing with women in, I wanna say, like February.” Which isn’t to say he stopped hangin’ around women. Quite the contrary. During camp for the Jones fight, Bailey went to the strip club every day. No dances, no sex. Instead, Bailey would bring in his dinner, eat, play the little electronic games, hang out with the girls, then go home when he got tired. He wasn’t lonely, but he’d split from the woman he was seeing and unused to being by himself, he liked to have someone around. It may have been unusual, but Bailey was drawing on his community to get him through a difficult time.

Bailey attributes his triumph over Jones to divine intervention, he can’t explain how it happened, but when Jackson abandoned Bailey, God prevailed. “That was the first uppercut I threw all year,” Bailey says of the eleventh-round bomb that overcame the worst training camp of his life. “Didn’t work on it, didn’t train it, the first uppercut I threw all year . . . God’s plan.”

So what you think about there being a dozen champions in each division, or the WBC’s efforts to exhaust the table of gems in increasing their absurd title catalog, is valid. But not all titles are equal, and their worth is in a significant way determined by the men who deplete themselves to acquire them.


Bailey was once one of those men. He had to get away from it, from the people who would jeopardize the life he has now, the wife, the four kids. “I’m happy, man, I’m good. I love comin’ home to my family, love gettin’ up in the mornin’ and goin’ to work.” You believe him too, because he’s so genuine, because you have a family too, and you understand the satisfaction that comes from doing what you can to provide for them. And so you’re happy for him. Happy endings are a rare thing in our sport, a sport that scavenges its elder statesmen, that turns men out into the wilderness of life beyond the ropes with no concern for where they end up.

But Randall Bailey got out in time.

Say it twice. Like he would. Let the echo drive the point home.


About Jimmy Tobin 107 Articles
Jimmy Tobin is a member of the Boxing Writers Association of America. His work has appeared in The Cruelest Sport, 15 Rounds, Undisputed Champion Network, Esquina Boxeo, El Malpensante, The Queensbury Rules, and The Fight Network. Jimmy is the author of Killed in Brazil? The Mysterious Death of Arturo “Thunder” Gatti, published by Hamilcar Publications. Connect with Jimmy on Twitter.