Floyd Mayweather: Ranking 10 Most Memorable Moments in Money's Career

Pound for pound superstar Floyd “Money” Mayweather has given fight fans a slew of data to interpret over the years. Fans’ interest level in the polarizing welterweight is simply astounding. Love him or hate him, you are interested in Floyd Mayweather.  

While more are sure to follow, here are the 10 most memorable moments of his illustrious boxing career to date. 

10. Mayweather Snags Olympic Bronze

The last time the 36-year-old welterweight officially lost a fight was during the 1996 Summer Olympics in Atlanta. Mayweather, the odds-on favorite to snag gold, had compiled an impressive 84-5 record as an amateur competitor. 

Dominant in the tournament until that point, Mayweather fell by points in a disputed decision loss to Bulgaria's Serafim Todorov. Mayweather's arm was raised momentarily after this featherweight semifinal before the referee corrected himself and awarded the win to Todorov.

The loud chorus of boos reverberating through the arena told Mayweather he deserved the win, but he didn't get a chance to compete for gold in the finals despite an official protest by Team USA. Still, Mayweather's Olympic medal would serve as a springboard to his professional career.

9. Rough Night with Jose Luis Castillo

Mayweather was an accomplished world champion by the time he met Jose Luis Castillo in 2002. A 4-1 favorite, he cruised through the first four rounds by keeping the hard-charging Mexican at arm's length.

But as the bout progressed, Mayweather experienced something he had seldom felt inside the ring: adversity. Castillo was constantly in the defensive-minded Mayweather's face, throwing shots up and down Mayweather's torso. As every round passed, Castillo seemed to grow stronger and stronger, ever successful at making it his kind of fight.

When the scorecards where read, though, Mayweather was awarded the disputed decision. The two fought a rematch months later. This time, Mayweather outboxed the slugger to help remove any lingering doubt about their previous encounter. 

8. Victor Ortiz and the Sucker Punch

September 17, 2011 was the day Floyd Mayweather delivered the sucker punch seen 'round the world. The ever elusive Mayweather was making Ortiz work through the first four rounds. Young lion Ortiz was aggressive but just couldn't seem to land like he wanted. Mayweather was too slick.

In what appeared to be simply an egregious lack of self-control, Ortiz intentionally headbutted Mayweather in the fourth round despite having just landed several punches. Referee Joe Cortez correctly stopped the action and penalized the offending Ortiz one point. 

Ortiz made several showy apologies to Mayweather. Cortez then restarted the action, but Ortiz was seemingly unaware (he was still looking over to the referee for instructions) when Mayweather took advantage of the opportunity and blindsided Ortiz with a vicious one-two combination that put him down and out for good.

7. Mayweather vs. Merchant

Sucker-punching Victor Ortiz wasn't the only controversial thing Floyd Mayweather did that fateful evening. 

After the bout ended, during the customary post-fight interview in the winner's corner, Mayweather got into a war of words with veteran HBO fight analyst Larry Merchant. 

"You never give me a fair shake. You are (expletive) and HBO should fire you. You don't know (expletive) about boxing. You ain't (expletive)..," screamed Mayweather. 

"I wish I was 50 years younger and I would kick your (butt)," Merchant responded.

Eventually, of course, the feud ended. Mayweather apologized to his longtime HBO pal Merchant after his 2012 win over Miguel Cotto. 

6. Mayweather Outclasses Corrales

In probably his most dominant display, Floyd Mayweather outclassed the previously undefeated Diego Corrales in 2001. The ever valiant Corrales was knocked down three times in the seventh and twice more in the 10th. 

Mayweather was blindingly fast in his 25th fight as a professional, and Corrales had no answer for his sharp counterpunches and quick strike offense. Corrales' corner threw in the towel after the fifth knockdown, realizing their guy was too tough for his own good. 

Corrales did not land any more than 10 punches in a round. It was complete and utter destruction of a world class fighter. If the fight world didn't know how special a talent Mayweather was up to this point, they certainly did now. 

5. Delivering on the PPV Stage

Despite being undefeated in 33 fights as well as considered one of the top pound-for-pound superstars in the sport, by 2005 Mayweather had yet to headline a major PPV card until he met fan favorite Arturo Gatti that June.

Fighting in front of his home crowd at the Boardwalk Hall in New Jersey did nothing for Gatti, who was obliterated by Mayweather in just six one-sided rounds. Promising to fight at a controlled distance went out the window for Gatti when Mayweather hit him flush in the temple in the first while Gatti was looking at the referee. 

By the sixth round, Gatti's eyes were almost swollen shut and his corner was forced to stop the fight. Final Compubox punch stats showed Gatti had landed just 17 percent of his punches, compared to 57 for the incomparable Mayweather. 

4. Mayweather Goes to Prison

By 2012, some fans had begun questioning Mayweather's willingness to take risks. The subject of him avoiding his most serious competition (e.g., Manny Pacquiao) had become frequent Twitter and message board banter.

Still, Mayweather couldn't do anything to avoid his problems outside the ring, including having to go to court for an incident involving the hair-pulling, punching and arm-twisting of ex-girlfriend Josie Harris while two of their children watched in September 2010. Mayweather pleaded guilty to a reduced battery domestic violence charge and no contest to two harassment charges to avoid up to 34 years in prison.

He was released for good behavior in February of 2013 after serving two of the three months to which he was sentenced.  

3. Mayweather Eclipses De La Hoya as Boxing's Biggest Star

A 2007 battle with Oscar De La Hoya established Mayweather as the premier fighter in the sport of boxing. The fight generated tremendous interest and served as a passing-of-the-torch moment from one box office star to another.

The fight itself didn't quite live up to the hype, but Mayweather's tremendous skill set was on full display for his largest audience yet. Thanks to numerous subplots (De La Hoya fired Mayweather's father as his trainer before the fight, this was Mayweather's first fight at the contract weight, etc.), the fight smashed numerous PPV records including buys (2.45 million) and domestic revenue ($136,853,700 million). The bout also generated $165 million in total gross revenue, the most for a fight ever.

Mayweather's speed and ring mastery were just too much for De La Hoya. He won the fight by split decision (116-112, 115-113, 113-115) though it probably should have been unanimous. With the win, Mayweather solidified himself as boxing's No. 1 celebrity, Floyd "Money" Mayweather.

2. Mayweather Ditches HBO for Showtime

Last February, Mayweather shocked the boxing community by announcing a six-fight mega deal with Showtime and parent company CBS. The deal allows Mayweather to fight on Showtime up to six times over the next 30 months. The first fight on the contract will be his May 4 clash with Robert Guerrero.

The deal turned out to have far-reaching ramifications. Within a month, HBO announced they would no longer purchase fights from Golden Boy Promotions, the promotional company Mayweather has used since his 2006 split with Top Rank.

HBO and Top Rank followed suite. Speaking to The Sweet Science's Michael Woods a day later, Top Rank's head honcho Bob Arum said as far as he was concerned, Showtime didn't exist.

So it's a new television landscape for fight fans now, thanks largely to the unparalleled bargaining power of Floyd Mayweather. Will fans benefit from the split? Or will too many fights continue to go unmade for boxing to thrive? 

1. The Fight That Never Was

It's perhaps unfair to say a moment that never occurred is the most memorable of a decorated champion's career, but in the case of Floyd Mayweather vs. Manny Pacquiao, it's quite warranted.

When Mayweather claimed retirement in 2008, few believed him. Seemingly at his peak as a fighter and in his physical prime, the 31-year-old had just pulled off stupendously lucrative wins over Oscar De La Hoya and Ricky Hatton. 

We were right to doubt.

Mayweather announced his comeback against Juan Manuel Marquez the very next year. A dominant win over Marquez, coupled with Manny Pacquiao's successive knockouts of Oscar De La Hoya, Ricky Hatton and Miguel Cotto, set the stage for what might have been the biggest fight in the history the sport. 

Except that it wasn't, because the fight never happened. And because of it, the most memorable moment of Floyd Mayweather's career for many is the fight that never was.

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