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Writer's pictureMatt Goddard

Floyd Mayweather Jr: from Pretty Boy, to Money May, to TBE

Floyd Mayweather Jr. is, rightly, one of the most celebrated, controversial, and successful boxers in the history of the sport. Widely regarded as one of the greatest defensive fighters of all time, Mayweather's undefeated 50-0 professional record (49-0 a more accurate record in my opinion), unparalleled boxing IQ, and astounding business acumen (with the help of very well selected advisors) have cemented his place as a boxing legend. His career can be divided into two clear and distinct phases: "Pretty Boy Floyd" and "Money Mayweather," each marked by different strategies, personas, and achievements. In addition to his career accomplishments inside the ring, Mayweather has also made headlines for his business ventures, including his highly successful TMT Promotions, and his post-retirement exhibitions, all contributing to his status as one of the richest and most successful athletes in history.


Early Life and Boxing Origins


Floyd Mayweather Jr. was born on February 24, 1977, in Grand Rapids, Michigan, into a family steeped in boxing. His father, Floyd Mayweather Sr., was a former welterweight contender who once fought the legendary Sugar Ray Leonard, while his uncles, Roger 'Black Mamba' Mayweather and Jeff Mayweather, were professional fighters as well. Roger Mayweather, who won world titles in two weight divisions, played an especially significant role in Floyd Jr.'s training and development.


Growing up, the young Floyd Mayweather's life was difficult and constantly challenging. His mother, Deborah Sinclair, struggled with drug addiction, and his father was often absent due to his own issues with the law. However, despite the challenges, Floyd Mayweather Sr. and Roger instilled in the young Mayweather the discipline and fundamental skillset that would shape him into one of the most technically proficient boxers in history.


Mayweather began boxing at the age of seven, and by his teenage years, he was already showing promise as a future star in the sport. His talent was undeniable, and he excelled as an amateur, earning the nickname “Pretty Boy” due to his elusive defence and his ability to avoid taking much punishment in the ring.



Floyd Mayweather Jr Amateur Boxing

Amateur Career


Floyd Mayweather Jr.'s amateur career was illustrious and set the stage for his professional success. He compiled an outstanding amateur record of 84 wins and only 8 losses, becoming one of the United States' most decorated amateur fighters. His achievements include:

  • National Golden Gloves Titles (1993, 1994, 1996): Mayweather won three U.S. national Golden Gloves championships at light flyweight, flyweight, and featherweight, showcasing his skill at various weight divisions.

  • 1996 Summer Olympics: Perhaps the most notable moment of his amateur career came at the 1996 Atlanta Olympics, where he represented the United States in the featherweight division. Mayweather won the bronze medal after an incredibly controversial semi-final loss to Bulgaria's Serafim Todorov. Many observers and boxing pundits felt that Mayweather had comfortably won the fight, and the outcome remains one of the most debated decisions in Olympic boxing history. Mayweather's emotional interview post-decision is worth a watch here.

Despite not winning the gold, Mayweather’s skill and potential were undeniable, and his Olympic performance, followed by the disappointing result acted to spur him on to the ultimate heights in his professional career which began later that year.



Pretty Boy Floyd Mayweather

Professional Career: "Pretty Boy Floyd" (1996–2007)


Floyd Mayweather Jr. turned professional in October 1996, immediately making an impact with his slick defence, speed, and offensive sharpness. He quickly built a reputation as a fighter to watch, earning the nickname “Pretty Boy” for his ability to avoid damage while delivering precise, clean punches with sharp combinations and spite. His early career was marked by a focus on his pure boxing abilities, content to work at mid-range, blending defence and offense masterfully.


Key Achievements as Pretty Boy Floyd:


  • First World Title: In October 1998, Mayweather won his first world title, the WBC Super Featherweight (130 lbs) Championship, by defeating Genaro Hernández. This victory marked the beginning of his dominance across multiple weight classes.

  • Lineal Championships: Mayweather won multiple lineal championships across different divisions, solidifying his place as one of the best pound-for-pound fighters of his era.

  • Five Division Champion: Mayweather won world titles in five different weight classes during this period—super featherweight, lightweight, light welterweight, welterweight, and light middleweight.


Top 5 Fights as Pretty Boy Floyd:


  1. Floyd Mayweather vs. Genaro Hernández (October 3, 1998)

    • Title at Stake: WBC Super Featherweight Championship

    • Significance: This was Mayweather’s first world title fight. He dominated the experienced Hernández, stopping him in the 8th round. It was the first step in Mayweather’s journey to boxing greatness.

    • Outcome: Mayweather won by TKO (8th round).

  2. Floyd Mayweather vs. Diego Corrales (January 20, 2001)

    • Title at Stake: WBC Super Featherweight Title

    • Significance: Mayweather faced the undefeated power-puncher Diego Corrales in what was supposed to be his toughest challenge to date. Mayweather put on a clinic, knocking Corrales down five times before Corrales’ corner stopped the fight.

    • Outcome: Mayweather won by TKO (10th round).

  3. Floyd Mayweather vs. José Luis Castillo I (April 20, 2002)

    • Title at Stake: WBC Lightweight Championship

    • Significance: Moving up to lightweight, Mayweather fought José Luis Castillo in a highly controversial bout. Castillo pressured Mayweather throughout, and many felt Castillo deserved the win, but Mayweather eked out a unanimous decision.

    • Outcome: Mayweather won by Unanimous Decision.

  4. Floyd Mayweather vs. José Luis Castillo II (December 7, 2002)

    • Title at Stake: WBC Lightweight Championship

    • Significance: The rematch saw a much sharper Mayweather, who left no doubt about his superiority by outboxing Castillo clearly, cementing his dominance in the lightweight division.

    • Outcome: Mayweather won by Unanimous Decision.

  5. Floyd Mayweather vs. Arturo Gatti (June 25, 2005)

    • Title at Stake: WBC Super Lightweight Championship

    • Significance: Mayweather completely outclassed the popular and tough Arturo Gatti, delivering one of his most one-sided performances. Gatti’s corner stopped the fight after six brutal rounds.

    • Outcome: Mayweather won by TKO (6th round).



Floyd Money Mayweather

Professional Career: "Money Mayweather" (2007–2017)


In 2007, Mayweather began to shift his focus from being just a master boxer to becoming a global brand and a self-promoting businessman. Adopting the moniker “Money Mayweather”, he embraced the flashy, flamboyant persona that became synonymous with his later career. This phase saw him focus on maximizing his earnings, turning every fight into a global blockbuster PPV event, and becoming a total superstar. During this time, Mayweather also refined his defensive style, prioritizing ring intelligence and risk mitigation over sheer aggression - particularly since he suffered with various hand injuries which diminished his power punching abilities.


Key Achievements as Money Mayweather:


  • Undefeated Record: Mayweather retired with a flawless record of 50-0, maintaining his dominance against all challengers.

  • Highest-Paid Athlete: During this period, Mayweather became the highest-paid athlete in the world, earning hundreds of millions of dollars from pay-per-view fights.

  • The Face of Boxing: Mayweather's fights against some of the biggest names in the sport turned him into a household name and elevated boxing to new heights in terms of revenue and popularity.


Top 5 Fights as Money Mayweather:


  1. Floyd Mayweather vs. Oscar De La Hoya (May 5, 2007)

    • Title at Stake: WBC Light Middleweight Championship

    • Significance: This was the fight that truly launched "Money Mayweather" into superstardom. Mayweather moved up in weight to fight the immensely popular Oscar De La Hoya. It was the highest-grossing fight in boxing history at the time, and Mayweather won a split decision in a close contest.

    • Outcome: Mayweather won by Split Decision.

  2. Floyd Mayweather vs. Ricky Hatton (December 8, 2007)

    • Title at Stake: WBC Welterweight Championship

    • Significance: Undefeated British superstar Ricky Hatton posed a serious threat to Mayweather’s perfect record. However, Mayweather outboxed and stopped Hatton in the 10th round, delivering one of his most impressive victories.

    • Outcome: Mayweather won by TKO (10th round).

  3. Floyd Mayweather vs. Shane Mosley (May 1, 2010)

    • Title at Stake: None (non-title fight)

    • Significance: In one of the few moments in Mayweather’s career where he was seriously hurt, 'Sugar' Shane Mosley rocked him with a massive right hand in the second round. However, Mayweather recovered quickly, not enabling Mosley to repeat the success of the overhand and dominated the rest of the fight to win a very clear victory.

    • Outcome: Mayweather won by Unanimous Decision.

  4. Floyd Mayweather vs. Canelo Álvarez (September 14, 2013)

    • Title at Stake: WBC and WBA Light Middleweight Titles

    • Significance: Mayweather faced the young and undefeated Mexican star Canelo Álvarez in a highly anticipated bout. Mayweather put on one of boxing's greatest masterclasses, easily outboxing the younger fighter and handing Canelo his only career loss (at the time).

    • Outcome: Mayweather won by Majority Decision.

  5. Floyd Mayweather vs. Manny Pacquiao (May 2, 2015)

    • Title at Stake: WBC, WBA, and WBO Welterweight Titles

    • Significance: Billed as the "Fight of the Century," this long-awaited clash between Mayweather and Filipino icon Manny Pacquiao shattered pay-per-view records. While the fight didn’t even remotely live up to the hype in terms of action, Mayweather’s defensive prowess, punch accuracy, shot selection and ring control earned him a comfortable victor

    • Outcome: Mayweather won by Unanimous Decision.



Floyd Mayweather Jr TBE

Other Notable Opponents


There's a long list of fantastic names on the Floyd Mayweather record (check the whole thing here) including Angel Manfredy, Carlos Hernandez, Phillip Ndou, Demarcus Corley, Sharmba Mitchell, Zab Judah, Carlos Baldomir, Juan Manuel Marquez (in one of the best technical performances I have ever seen), Victor Ortiz, Miguel Cotto, Robert Guerrero, Marcos Maidana (twice) and Andre Berto. All of these fights, in my opinion, were elite opponents on a record that would've been excellent with these names all removed. Mayweather fought 23 former or current world champions during his professional career - a huge number. That for me, no matter your opinions on his persona or character, deserves a great deal of respect and admiration.


Post-Retirement and Exhibition Fights


Mayweather officially retired from professional boxing after his 50th fight—a knockout victory against UFC star Conor McGregor (in McGregor's professional boxing debut) on August 26, 2017. The crossover event between boxing and mixed martial arts drew massive global attention and generated over $600 million in revenue, further solidifying Mayweather’s position as a financial juggernaut and the true cash cow of combat sports.


Since retiring, Mayweather has participated in several exhibition matches, including bouts against elite kickboxer Tenshin Nasukawa and YouTuber Logan Paul, adding millions to his earnings without risking his undefeated record and bringing boxing to a new audience.



Floyd Mayweather Jr, The Businessman

The Money Team (TMT Promotions)


In addition to his in-ring accomplishments, Mayweather has built a business empire through TMT Promotions (The Money Team), a boxing promotional company that manages fighters and organizes events. TMT Promotions has become a key player in the sport, and Mayweather’s business acumen (or that of his employees) has allowed him to retain much of the revenue from his fights, making him one of the highest-earning athletes of all time.


Career Earnings and Financial Accolades


  • Total Career Earnings: Mayweather has reportedly earned over $1.1 billion throughout his career, making him one of only a few athletes to reach the billionaire milestone.

  • Highest-Paid Athlete: Mayweather has topped Forbes’ list of the highest-paid athletes multiple times, largely due to his pay-per-view numbers and lucrative sponsorship deals.

  • Top Grossing Pay-Per-View Fighter: Mayweather holds several of the top spots for the highest-grossing pay-per-view events in boxing history, including his fights against Pacquiao, Canelo, De La Hoya and McGregor.


My Personal Opinion


As a young boxer during the Mayweather era, I was captivated by Floyd's style. His intelligence in the ring, fluid movement, composure, and precise jab showed technical boxing at it's finest. As a boxing purist, I found his performances consistently impressive. Although I admired the great Miguel Cotto more for his demeanour and character outside the ring, there's no denying Mayweather's ability to embrace the role of the "villain" helped him to build his financial empire. He drew fans, most often hoping for his defeat, but his unmatched work ethic, mental toughness, and composure on fight night ensured no one could overcome him in the ring. While a few decisions could be debated, from a boxing perspective, Floyd Mayweather has earned his place among the upper echelons of boxing record books alongside the sport's greatest achievers.


Conclusion


Floyd Mayweather’s career is a blend of unparalleled boxing talent, defensive mastery, and astute business decisions. His legacy extends beyond his undefeated record, as he revolutionized how boxers approach the business side of the sport (particularly with self-promotion and PPV revenue commission). Whether he’s remembered as "Pretty Boy Floyd", "Money Mayweather" or "TBE", there’s no denying that Mayweather is one of the greatest fighters and one of the most financially successful athletes in history. His legacy will continue to influence and impact boxing and sports for generations to come.


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