Floyd Mayweather Jr. and the 20 Biggest Bad Guys in Boxing History

By now most boxing fans will have heard that Floyd Mayweather Jr. will be spending the first three months of 2012 locked up on domestic battery and harassment charges. With good behavior, he should get out in 60 days. 

This was a very ugly incident, a drawn-out episode in which Mayweather reportedly beat his then-girlfriend and threatened their two children, ages nine and 10. Mayweather's 10-year-old son reportedly fled to get help. The judge who sentenced Mayweather stated that it was fortunate the situation did not end up escalating further.

Professional prizefighting is a brutal, unforgiving sport. It has never been any secret that those who are great at it are often driven by the kind of demons that create terrible problems for them in day-to-day life. A list of pro boxers who have gotten into some sort of trouble for being violent outside of the ring would be very long.

Even without beating women in front of their children, Mayweather Jr. has been boxing's premier "heel" for close to a decade. While it is true that he has a strong base of loyal fans, an even bigger group of fans pay their money in the hopes of seeing Mayweather get his ass kicked. This most recent domestic violence rap will make the second group even bigger.

For the list that follows I have two or three different categories of "bad guys."

I have included some cases of boxers who have had legal problems which effectively destroyed their careers, or else their lives post-career.

I have also included fighters, or former fighters, who the public just generally seem to regard as jerks. Some of these, like Mayweather, have been very successful at selling tickets and PPVs to people who want to see them get knocked out.

Finally, I have included a few examples of fighters who were (unfairly) portrayed as villains by the media of their day.

Floyd Mayweather Sr.

Floyd Mayweather Sr.'s long history of feuding and bickering with his son is well known and was vividly documented on HBO's 24/7 series during the buildup to the Mayweather-Ortiz fight. Floyd Sr. is probably the one adversary against whom the majority of the public sides with Floyd Jr.

But truly this is a case where the apple has not fallen far from the tree, as father and son have the same brash and flashy personality.

In his day Mayweather Sr. was a skilled defensive boxer and welterweight contender. His fight on Wide World of Sports against a pre-champion Ray Leonard was a textbook example of a tough, crafty fighter skirting the rulebook to rough up a more talented and explosive fighter, though ultimately the young Sugar Ray did knock him out.   

Matt Remillard

At the start of 2011, Matt Remillard was a talented featherweight prospect. He was the undefeated NABF featherweight champion, prior to dropping the belt to Mikey Garcia last March.

Currently he is serving a five-year sentence for assaulting another man with a baseball bat and fracturing his skull. It was reportedly a fight over a woman. Considering the weapon he chose to use in this altercation, he is lucky to not be serving a much longer sentence for homicide.

At only 25 years of age, there is a chance Remillard can still turn his life, and possibly even his career, around.   

Ike Ibeabuchi

There was a time in the 1990s when many boxing fans felt that Ike Ibeabuchi was destined to be the next big thing at heavyweight. The Nigerian native still has a perfect 20(15)-0 record. He recorded a brutal knockout of former champion Christ Byrd. His unanimous-decision victory over David Tua is one of the legendary heavyweight slugfests of all time, with the two men setting the record for punches thrown in a heavyweight fight. 

Unfortunaty Ibeabuchi has spent this entire century in prison, for charges stemming from a sexual assault. 

Ibeabuchi, according to numerous reports, clearly had very serious mental health issues. His first brush with the law came when he kidnapped his former girlfriend's teenage son and crashed his car, severely injuring the boy. Ibeabuchi, who was reported to be preoccupied with "demons, was given only two month probation and an undisclosed cash payment to the mother.  

Eventually things came to a crisis point when Ibeabuchi was arrested for attempted rape at the Mirage Casino in Las Vegas. He was sentenced in 1999 on multiple counts of assault and attempted sexual assault. He may be paroled in 2012, but will certainly face deportment if he is. 

Kid McCoy

At the turn of the 20th century, Kid McCoy was one of the most talented and colorful fighters on the planet. Tall and slender, McCoy was a master of scientific boxing and also, apparently, of dirty tricks. 

The stories about McCoy's guile have  a folklore quality. The old "your shoelaces are untied" trick is credited to McCoy. During his barnstorming, exhibition fighting career, he reportedly had his corner throw tacks into the ring while he was battling a much larger opponent who was fighting barefoot.

McCoy fell into economic dissolution in retirement. He enticed a wealthy woman named Mor to leave her husband. She was later shot dead in McCoy's apartment. McCoy went on a hostage-taking spree before finally being captured.

His trial in 1924 was a media sensation. He was convicted of manslaughter and sent to San Quentin. Paroled in 1932, he took his own life in 1940.   

Jack Johnson

The first black heavyweight champion, Jack Johnson has become a cultural hero in the century since he ruled the boxing world. His swaggering audacity and uncompromising commitment to living how he pleased as a black man at a time of virulent cultural racism is rightfully viewed as nothing short of heroic. 

But during his actual career, the mainstream press treated him as the sporting world's ultimate villain, a threat to the very order of society. Leading lights of American literature such as Jack London loudly called out for a "white hope" to "wipe the golden smile from Johnson's face." 

Johnson seems to have reveled in the white anxiety he provoked and eventually the authorities used spurious legal means to persecute Johnson and drive him from the country. After Johnson dropped the title to Jess Willard in 1915, promoters did not let another black man fight for the title until Joe Louis emerged decades later. 

Muhammad Ali

Muhammad Ali is kind of like the modern Jack Johnson. Today he is regarded as one of the most beloved athletes of the past half-century: Olympic gold medalist, world champion, cultural icon. In his own words, "the greatest."

But it was not always so. During the turbulent 1960s he was stripped of his title and nearly sent to prison for protesting the Vietnam War by refusing to allow himself to be inducted into the Army as a draftee. For the American power establishment, the Black Muslim Ali was cultural enemy No. 1. 

But even before Ali took his big political stand, he had already earned the nickname "The Louisville Lip" for his brash, outspoken persona. In his autobiography he admitted to having deliberately modeled his promotional style after professional wrestler Gorgeous George. From the earliest days of his professional career, a high percentage of fans just wanted to see him get punched in his big mouth. 

Ali, of course, was emblematic of the changing times. Even when he was at the height of his "outlaw" status, he was attracting an ever-expanding pool of fans worldwide who appreciated his willingness to risk everything for what he believed in.

Max Schmeling

In 1938, with World War Two approaching like a freight train, Joe Louis defended his world title against German Max Schmeling. Schmeling was a former world champion, the only man to have beaten the young phenom Louis and a personal favorite of Adolf Hitler.

In the press coverage for the fight, Joe Louis became not just a boxing champion, but a champion for American democracy and the melting pot. Schmeling was the flag carrier for the German attitudes of racial superiority.

Louis' ensuing one-round destruction of Schmeling was so culturally momentous that it was still profiled in my junior high school U.S. history book over 40 years later.

In truth, Schmelling was never a member of the Nazi party. At worst he can be accused of hobnobbing with Hitler and other Nazi bigwigs in a situation where he probably had no alternatives short of fleeing Germany outright. After he lost to Louis, the Nazis dropped him and he served during the war as a common soldier. 

In retrospect, he appears to have been a decent man. In 1938 Schmeling personally hid two Jewish children and aided their escape during the purge of Berlin, an incident he kept private for years out of a sense of modesty in face of the much greater tragedy that still occurred.

When the IRS viciously hounded Joe Louis in retirement, former opponent Schmeling was a far more generous friend to the great American champion and army veteran than his own government proved to be.

Andrew Golota

Heavyweight contender Andrew Golota, Warsaw, Poland native and former Olympic bronze medalist was so notorious for illegal tactics that he was eventually nicknamed "The Foul Pole" by sportswriter Michael Katz. 

While working his way up though the ranks he bit Samson Po'hua on the shoulder. But his greatest moment as a dirty fighter came when he fought Riddick Bowe for the title, in what The Ring dubbed "The Riot in the Garden."

Well ahead of the champion on the scorecards, Golota appeared more worried about destroying Bowe's capacity to reproduce than about winning the actual fight. Even as he appeared to have Bowe on the ropes in the seventh, he continued to foul, forcing the referee to disqualify him. Pandemonium proceeded to break out as the ring was swarmed by partisans from both sides and overwhelmed security. 

The rematch was highly anticipated and once again, Golota managed to lose a fight he was winning due to disqualification. 

Riddick Bowe

Riddick Bowe actually had a pretty positive image during his career. My own opinion is that a lot of the credit for this probably should go to Bowe's manager Rock Newman, along with Bowe's own Olympic pedigree, at a time when Olympic medals in boxing still had important cache among sports fans.

Even during his career Bowe sometimes drew criticism for being less than disciplined in his training. When he threw away the WBC strap rather than defend it against Lennox Lewis, it was a major disappointment for fans.

Bowe's life has been a disastrous in retirement, with bizarre and violent legal problems such as assaulting his sister and later assaulting his former wife. He was also convicted of kidnapping his wife and children.

He was given leniency in his sentencing due to his claims of having brain damage. However, brain damage or not, he later returned to the ring in 2005 and 2008. 

Mike Tyson

These days, Mike Tyson seems to be culturally redeemed—cracking people up on celebrity roasts and in movie cameos. But during his career, Mike Tyson was probably the scariest bad guy of all time. 

There was the rape conviction, the ear-biting, the threats of cannibalism against Lennox Lewis' children, the extracurricular street fighting, the charges of spousal abuse and the routine menacing of reporters. The guy who had looked like he had the potential to go down as the greatest heavyweight of all time instead developed into the sport's greatest freak show. 

Like I said, Tyson seems to have found some measure of peace in recent years. As a boxing fan who grew up in the '80s, it was nice to watch him get inducted into the Hall of Fame last year. But there has to be a place for Iron Mike on any list like this. 

Jame Toney

James Toney is one of the most talented professional boxers of the past 20 years. As a trash talker he is nearly without peer, a combination of Ali's creativity with Tyson's brutal aggression. He doesn't mind offending people, because, after all, fighting is what he is all about. 

When big-money fights stopped being available for Toney he was able to more or less thug in his way on camera into a $500,000 payday against Randy Couture in the UFC. The link above shows him drumming up promotional excitement for his special-rules fight with Ken Shamrock, which is supposed to take place some time in 2012. 

Calling Toney a "Bad Guy" is subjective. He's brash, aggressive and not afraid of confrontation. But if he is a bad guy, he has managed to make it work for him and used it to keep working well beyond most of his peers. 

Ricardo Mayorga

It anybody trumps James Toney as a trash talker, it's Ricardo Mayorga, the man The Ring once referred to as the "craziest man in boxing."

Some of his most obnoxious moments have come against Oscar De La Hoya and Miguel Cotto, two of the sport's most popular stars. In true storybook-villain form, he went down to inglorious defeat both times.  

Nasseem Hamed

I always found Nasseem Hamed's over-the-top entrances and cocky antics annoying, but I'll give him credit for being able to mostly backing all up all that strut. He had tremendous hand and foot speed, to go with catlike balance and reflexes.  

There is no denying he had a big fanbase and was a fighter who people wanted to see fight. But I take satisfaction that when he stepped up to face an old-school great like Marcos Antonio Barrera, he ultimately had less substance than the Mexican champ. 

Fernando Vargas

When Oscar De La Hoya was at the height of his career as the "Golden Boy" Fernando Vargas launched a campaign of publicly insulting the Olympic gold medalist, positing himself as the "bad guy" in order to talk himself into a lucrative payday. I can still remember him referring to De La Hoya as "my son" on the Jim Rome Show. 

When they ultimately met in the ring, Vargas followed the bad-guy script, going down to the hero in 11. After the fight he tested positive for banned PEDs.  

Vargas' last fight in 2007 was an exciting majority-decision loss to fellow bad guy Ricardo Mayorga. To nobody's surprise, the buildup to the fight was hostile and the action was hotly contested. 

Though Vargas embraced the brash, trash-talking role, he always did retain a certain down-to-earth quality that ultimately made him a pretty popular boxing figure. Like James Toney, he's a guy that made playing the bad guy pay off.  

Zab Judah

If Zab Judah isn't disliked by more sports fans than Floyd Mayweather Jr. then it is only because he is less well-known. He has all of Mayweather's cocky swagger, just quite a bit less talent.  

Judah's meltdown after getting KO'd by Kostya Tszyu is probably the most embarrassing thing I've ever seen occur in a boxing ring. 

William "Caveman" Lee

My only memory of William "Caveman" Lee's career is of watching the 1983 fight linked here against Marvin Hagler, in which he got smashed inside the first round. But Al Berstein ranked the fifth round of his fight with John LoCicero, in which Lee ultimately knocked his opponent out, as the best round he'd ever seen, ahead even of Hagler/Hearns.

Lee hit trouble in his post-career years, serving three stints for armed robbery.  

Antonio Margarito

By getting caught trying to fight with plaster-loaded hand wraps against Shane Mosley, Antonio Margarito ensured that he would forever be viewed as a bad guy by most boxing fans, especially since his last fight before Mosley had been a TKO victory over the very popular and undefeated Miguel Cotto. 

As with other members of this list, wearing the black hat has had certain career benefits for Margarito. Over the past two years he has made a lot of money getting his eye punched shut by two of the sport's most popular fighters, first Manny Pacquiao and then in a long-awaited rematch with Cotto. 

Luis Resto

Before Antonio Margarito there as Luis Resto. In 1983 he upset undefeated prospect Billy Collins, pulverizing his face in the process. Immediately after the bout, Collins' father discovered that Resto had removed the padding from his gloves, as can be seen in the linked video. 

Resto and his trainer Panama Lewis both served two-and-a-half years for the incident. It was famously profiled in the HBO documentary Assault in the Ring. 

Tony Ayala

On January 1, 1983, at the height of his career, Tony Ayala Jr. burglarized the home of his schoolteacher neighbor and sexually assaulted her. Although he was only 19 years old, it as his third assault against a woman and he was sentenced to 35 years.

At the time, Ayala was scheduled to meet Davey Moore for the title. He had already been on the cover of Sports Illustrated. Angelo Dundee has said he thought Ayala could have been one of boxing's greatest fighters.

After serving 16 years in prison, Ayala got out of jail and resumed his career. In 2004 he was shot by a woman after breaking into her house. Later in 2004 he was pulled over for speeding, caught with drugs and sentenced to an additional ten years for violating probation. 

Carlos Monzon

Carlos Monzon of Argentina was, in my estimation, the greatest middleweight champion of all time. During the 1970s he ruled the 160-pound division. In South America he as a celebrity, notorious for slapping around starlet girlfriends and noisy reporters. 

In 1988, years after retirement, he was sentenced to 11 years in prison for killing his wife Alicia Munoz. He died in a car crash in 1995 while on a weekend furlough.