Standing Count: The Six Biggest Heels In Boxing Today

When Jake “the Snake” Roberts held a cobra to a helplessly ensnared Randy “Macho Man” Savage and the cobra sunk his fangs into the Macho Man’s shoulder, I was enthralled. When the “Million Dollar Man” Ted DiBiase broke out his inimitable cackle or The Undertaker slammed an opponent into a casket or the “Nature Boy” Ric Flair crowed, “To be the man, you gotta beat the man,” I was captivated.

I’ve always been enamored with “heels,” the bad guys, be it in professional wrestling or in boxing. While boxing is a true sport and wrestling is eloquently described nowadays as “sports entertainment,” they share similarities many of us would probably rather ignore. Not me. The following is a carefully considered, objectively reasoned, and utterly biased list of the biggest heels in boxing, the guys we love to hate, pay to see lose, and will ultimately cheer when they are inducted into the International Boxing Hall of Fame (ok, not all of them). My extremely loose criteria include a history of behavior to raise the ire of fans, enough success to justify their continued presence on the boxing landscape despite said behavior, and an oversized or cartoonish persona that entertains even as they irritate.

With all the animosity and unrest among boxing fans, I figured I might as well add fuel to the fire. (Yeah, I’m not too popular.) On to the list, including heel credentials:

1. Floyd “Money” Mayweather – The inspiration for this list, the boxer formerly known as “Pretty Boy” adopted Ted DiBiase’s Million Dollar Man gimmick and added a hip-hop twist. Floyd is the preeminent heel fighting today. His recent demand for Olympic-style blood testing that ultimately derailed his March showdown with Manny Pacquiao only elevated his heeldom to a new level. Heel credentials: Unbridled arrogance about his ability in the ring; extravagant flaunting of his wealth, even when burdened with tax issues; allegations from numerous boxing writers and fans of ducking difficult challengers (including, among others, Shane Mosley, Miguel Cotto, and Kostya Tszyu) to maintain his undefeated record; run-ins with the law including a search of his Rolls Royce following a shooting last year; oft-hilarious run-ins with the media, including Brian Kenny and R.A. the Rugged Man; scuttling the hotly anticipated matchup with Pacquiao with his blood test demands.

2. “The Bobfather” Bob Arum – Notorious for both his impressive intellect and volcanic temper, Arum is somewhat akin to Vince McMahon in that he is something of an evil puppet master. Except while some of Vince’s shtick is “kayfabe” (a wrestling term for “fake” or “part of the story/character”), Arums’ elaborate flaws are all real. Heel credentials: That aforementioned temper and a general tendency to let his emotions, rather than his intelligence, dictate his behavior and decisions; longstanding feuds with Mayweather, Jr. and Oscar de la Hoya that prevented numerous great fights from happening over the years; fined $125,000 in 1995 for bribery; unabashedly supported Antonio Margarito after elements of Plaster of Paris were found in Margarito’s gloves, going so far as to accuse the California State Athletic Commission of racism after the commission suspended Margarito, even though Arum also represents Miguel Cotto, who may have been a victim of Margarito’s cheating in their fight; referred to UFC fans as skinheads and homosexuals; played a key role himself in the failed Pacquiao-Mayweather negotiations.

3. The World Sanctioning Organizations (The wSo) – In the vein of heel factions like the New World Order (nWo) or the Four Horseman, the influence of the sanctioning organizations is only surpassed by their secrecy and destructiveness. Heel credentials: diluting the value and importance of championship belts; stripping titlists and inventing titles out of greed for sanctioning fees; the IBF bribery scandal of the late-1990s, among other charges of corruption against various bodies; confusing and alienating casual boxing fans while simultaneously infuriating hardcore followers; introducing such worthless concepts to the sport as interim champions, super champions, emeritus champions, and diamond belts; constantly putting short-term greed ahead of the best interests of boxing.

4. Antonio “Margacheato” Margarito and Javier “Captain Corrupt” Capetillo, “The Plaster Blasters” – The preeminent heels in the boxing tag-team division (which I just made up), they made an aggressive heel turn when elements of Plaster of Paris were found in Margarito’s gloves prior to a fight with Shane Mosley. Heel credentials: attempting to load Margarito’s gloves with Plaster of Paris for his fight with Mosley; subsequently refusing to accept any culpability for wrongdoing; clouding previous fights with Miguel Cotto, Kermit Cintron, and others with suspicions of similar cheating; inciting particular suspicion over Margarito’s thrilling PPV win over Cotto in which Cotto’s face was a mask of blood by the end; adding ongoing disgrace to the sport with Margarito attempting to get his license back and Capetillo continuing to act as a trainer in Mexico despite his criminal acts.

5. “The Golden Boy” Oscar De La Hoya – Perhaps most comparable to Hulk Hogan’s late-career heel turn in the late 1990s, De La Hoya spent more than a decade as the biggest “face” (good guy) in the sport before his recent turn. Heel credentials: latest in a long line of men who promised to “clean up boxing” and gave us business as usual; promoting his own agenda with suspicious and potentially defamatory blog posts; raising concerns over the credibility of Ring Magazine by purchasing the “Bible of Boxing” while he also runs a promotional company; cultivating a suspicious relationship with HBO, resulting in unrest among other promoters and some observers like Thomas Hauser; generally giving the impression that he is incapable of sincerity; his terrible, terrible, terrible blog deserves another mention.

6. Don “Only in America” King – Not long ago, King would have topped this list, but his influence has waned in recent years. Yet he remains the most iconic villain in the sport, a grinning demon with wild hair waving miniature flags, crowing his trademark catchphrase, “Only in America!” Heel credentials: well, he killed two guys and was convicted for manslaughter in one of those cases, so there’s that; a career-long trail of disgruntled fighters and lawsuits over money and other issues, most recently with Nate Campbell; signing talented young fighters and failing to develop them properly, leaving them on the shelf for extended periods; remember, he killed two guys.

Honorable mentions:

Bernard “The Executioner” Hopkins – He just missed the list and probably deserves a spot but I got lazy. With “I’ll never lose to a white boy,” disrespecting the Puerto Rican flag in Puerto Rico and the executioner mask just in his recent past, his resume is outstanding.

David “The Hayemaker” Haye – The big mouth is entertaining and the Klitschko decapitation t-shirt and subsequent failure to fight either brother was infuriating, but his credentials are a little thin beyond that. He’s on the rise, though.

James “The Austin Outlaw” Kirkland – Another guy who probably should have made the list, Kirkland was the darling of hardcore boxing fans for his relentless pressure style, unusual training methods with trainer Ann Wolfe, and his rise from a difficult background to impending stardom. Then he was arrested on gun charges. Now, fans’ resentment builds as Kirkland rots behind bars. The typical boxing feel-bad story.

Also considered:

Edwin “The Liquidator” Valero, Paulie “The Magic Man” Malignaggi, James “Lights Out” Toney, “Iron” Mike Tyson, Michael “The Donk” Koncz

About Tim Starks

Tim is the founder of The Queensberry Rules and co-founder of The Transnational Boxing Rankings Board ( He lives in Washington, D.C. He has written for the Guardian, Economist, New Republic, Chicago Tribune and more.