Floyd Mayweather reflects on his iconic victories over Manny Pacquiao and Canelo Álvarez, sharing who he found tougher and reigniting the debate about boxing’s greatest of all time.

Floyd Mayweather, the boxing legend, retired in 2017 with an impeccable 50-0 record, defeating some of the greatest boxers in history. Among his most notable victories are those over Manny Pacquiao and Canelo Álvarez, both of whom he outclassed on points.

The fight against Pacquiao in May 2015 remains the most successful pay-per-view event in boxing history. Meanwhile, Mayweather handed Canelo his first professional loss in September 2013, showcasing his dominance against the rising star.

During an interview on the “Million Dollaz Worth Of Game” podcast, Mayweather reflected on these victories, stating that Manny Pacquiao was the tougher opponent of the two and the most challenging fighter he has ever faced.

Mayweather on Pacquiao: “A Hell of a Fighter”

“It’s because of his movement. He’s a hell of a fighter, and I can see why he won so many fights, and I can see why he’s going down as a Hall of Famer. It’s just certain moves he makes,” Mayweather commented, praising the Filipino icon’s unique style and accomplishments.

Mayweather’s Brutal Honesty About Canelo

In contrast, Mayweather was more dismissive when discussing his fight with Canelo Álvarez. “You can take a guy like Canelo. I’ll tell the truth about Canelo. The (expletive) was easy. A cakewalk, easy. You’re all praising this dude. He was nothing. I was almost 40, and I cooked this dude, easy.”

Mayweather’s blunt remarks highlight his confidence in his performance against Canelo, whom he defeated with remarkable ease despite being well past his physical prime.

The Eternal Debate: Boxing’s Greatest of All Time

Though Mayweather retired undefeated, his legacy continues to spark debates among fans and experts alike. His recent comments reignite the discussion about who truly deserves the title of the greatest boxer of all time. With victories over two legendary fighters like Pacquiao and Canelo, Mayweather’s career remains a cornerstone of modern boxing history.

Oscar De La Hoya was looking for an alternative to Floyd Mayweather when the idea of him fighting Manny Pacquiao, then a lightweight, was first proposed.

It was none other than the respected HBO analyst Larry Merchant who first detected the ability in them to combine in an occasion capable of transcending boxing, but when he did so Pacquiao, for all of his undoubted ability, had never fought above 135lbs.

HBO Boxing had largely come to define the sport during what represented the glory era of the noughties.

Their 24/7 series had first enhanced De La Hoya’s standing as the world’s highest-profile figure and contributed to Floyd Mayweather succeeding him in that status; when De La Hoya vs Pacquiao was signed for December 6, 2008, it then started the process of transforming the exciting Pacquiao into a crossover star.

If De La Hoya had been frustrated by Mayweather’s refusal to commit to a rematch – in May 2007 Mayweather had earned a split decision over him at super-welterweight – Pacquiao had come to represent the next most lucrative opponent.

Pacquiao had also been viewed as fortunate to earn a decision over Juan Manuel Marquez in March 2008 at super-featherweight – it was widely concluded that even after impressing in victory over David Diaz at lightweight three months later, he would be too small to trouble De La Hoya, who had previously fought at 160lbs.

“The size difference won’t be a big deal to me or Manny,” said the “Golden Boy” when their welterweight contest was agreed to.

“I understand the relentless style Manny has. For me, as a 35-year-old fighter it really is a big challenge to me. I felt challenged, especially from an expert trainer who trained me and trains Manny.

“He knows my style and knows Manny. If he thinks I can’t pull the trigger, we’ll see December 6.”

A building is purchased on Sixth Avenue, on the corner of 47th Street, in Manhattan

Floyd Mayweather, the boxing champion with a 50-0 career record, has once again shown that he has no qualms about splashing the cash. The American boxer, who boasts on his social networks of his acquisitions (he collects high-end cars, watches, poses with wads and wads of bills…), is one of the sportsmen who has earned the most money in the history of sport (more than 1.2 billion).

If in October it was revealed that he had spent more than $402 million to buy 60 New York buildings that will have more than 1,000 affordable homes in Upper Manhattan and that in November he acquired a stake in the Versace Mansion in Miami, now he has spent more than $20 million of his wealth to acquire a building on Sixth Avenue, according to TMZ.

This property is located on a corner at Sixth Avenue and 47th Street in Manhattan. It has offices, a diamond buying and selling store… and even a large billboard, the kind that delights tourists who flock to the Big Apple

“When I was young I used to shop at that Diamond store. I never thought I would end up owning this important property at the entrance to 47th Street. With hard work and dedication anything is possible,” Mayweather said in a statement. The boxer’s wealth is estimated to have reached $1.5 billion in 2024.

Floyd Mayweather has assured that generational wealth stays in his family for years to come.

‘TBE’ hung up his gloves in 2017 after pocketing a mammoth $1.2billion (£800m) in career earnings, making him the highest-paid boxer of all time.

Over the years, Mayweather has splashed his cash on various lavish items such as a £40,000 diamond-encrusted iPod, a £10,000 one-of-a-kind golf buggy and a fleet of supercars worth over £20m.

But more recently he has focused his outgoings on building up a large property portfolio for long-term investment.

His vast property empire includes a Las Vegas mansion he bought for $10m (£7.6m), a $18m (£13.8m) Miami Beach compound in the Palm Island conclave and a $402m (£309m) block of New York apartments.

However, his most recent $20m (£15.9m) purchase has been gifted to his three-year-old grandson, Kentrall Gaulden Jr.

Mayweather has entered into an agreement to purchase a prominent building in New York City for ten figures.

The property is located on 6th Avenue and 47th Street in Manhattan and comes complete with offices, a diamond exchange, and a large, income-generating billboard.

Mayweather regularly frequented the diamond district, which is now owned by his grandson.

“I never thought I would end up owning this important property at the entrance of 47th street…

“Through hard work and dedication anything is possible.”

Mayweather uploaded a video of him gifting the building to his grandson to his Instagram

“You are the first kid that owns a building in the diamond district in New York City.”

Kentrall smiled and wrapped his arms around his grandad.

‘Money Mayweather’ may be flashing his cash now but it wasn’t always this way.

The five-weight world champion grew up in a one-bedroom apartment with six relatives in New Brunswick, New Jersey.

“When people see what I have now, they have no idea of where I came from and how I didn’t have anything growing up,” he told Mercury News in 2007.

His story now serves as a reminder of how boxing can change lives.

Bob Arum has seen it all in the sport of boxing, including one of its biggest stars in history, Floyd Mayweather.

Though there was no love lost between the promoter and fighter when Mayweather split from Top Rank and went out on his own, Arum saw up close and personal just how skillful the 47-year-old was in his prime.

Famously, no man could beat Floyd in the ring, though some came close. He retired with a perfect 50-0 record with victories over the likes of Oscar De La Hoya, Manny Pacquiao, Miguel Cotto and Shane Mosley.

The latest dominant American in the sport is one Terence Crawford, the switch-hitting four-division world champion whom Arum also promoted before a split.

The 93-year-old promoter was asked about a fantasy match-up between Crawford and Mayweather by ES News and confidently backed the current champion.

Floyd Mayweather is widely regarded as the greatest boxer of the modern era with his perfect 50-0 record – a one-of-a-kind accolade. His technical prowess, world-class defensive skills, and his punching accuracy always saw him get the better of his rivals. However, in one of his toughest outings, the world saw Mayweather getting toyed with by Emanuel Augustus before ‘Money’ Mayweather found the TKO victory in the 9th round, which Joe Rogan recently claimed to have found amusing.

Among the wide array of showboaters in boxing, Emanuel Augustus surely tops the list. The former boxer competed in a mind-boggling 78 professional bouts, racking up a mixed record of 38 wins and 34 losses (and six draws), but that’s not what he was known for. In fact, Augustus showcased one of the most awkward boxing styles, which proved to be a big problem for Floyd Mayweather when they fought in 2000.

Although Floyd Mayweather managed to knock the ‘Drunken Master’ out, which Emanuel Augustus was so often called, ‘Money’ Mayweather would admit later that he had to dig deep when he was in the ring with his former rival, something that Joe Rogan seems to agree with. During episode #2235 of JRE, the host told guest Mike Rowe, “He gave Floyd a hard f***ing time because he’s so difficult to fight… [Reacting to Augustus’s highlights] How do you deal with that?”

While showering praise on how good of a boxer Floyd Mayweather was, Joe Rogan also gave credit to Emanuel Augustus for his awkward, yet effective style. “When you’re a guy like Floyd and you’re getting clowned – the cream of the crop, Olympian, I mean you’re a f**king phenomenal boxer, just a fantastic boxer – and then you’re fighting this guy who’s dancing in front of you, but also really good. It wasn’t just that, like you rarely get a guy who’s clowning like that but also [has] that kind of head movement skill. Phenomenal movement.” Joe Rogan stated.

Meanwhile, his guest, TV personality Mike Rowe, wondered what went into Emanuel Augustus’ training that made his boxing so awkward but effective. Well, Joe Rogan believes that these are those kinds of things that can never be taught.

Joe Rogan believes Floyd Mayweather’s former rival’s awkward style comes to him naturally

In any form of combat sports, coaches always emphasize the importance of technique, and boxers like Floyd Mayweather and Mike Tyson, among many others, have proved how essential techniques really carve a fighter’s path to success. This is a reason why Joe Rogan doesn’t believe that the style Emanuel Augustus had was something that was taught in training.

“I don’t think anybody trains you to do that. [Someone like Cus D’Amato] he would never [allow it],” said Joe Rogan. However, he does seem to believe that if fighters naturally develop their own way of fighting, with a unique flair, there might be certain exceptions where coaches could play to those fighters’ strengths – but only if they find success consistently.

Is it fair to compare the consensus GOATs of two different sports like MMA and boxing? Well, UFC color commentator Jon Anik certainly thinks so. In a recent conversation in MMA Junkie, Anik claimed that Jon Jones has surpassed Floyd Mayweather, not just as a fighter but as an all-time great. Bold words, right? But Anik’s reasoning isn’t without nuance, he highlights Jones’ ability to thrive in the unpredictable realm of mixed martial arts. Yet, it begs the question, are we comparing apples to oranges when debating UFC versus boxing legacies?

“I think, with respect to Joe Calzaghe and Floyd Mayweather, Jon Jones has already pushed himself beyond those guys,” Anik stated. “Even if people want to denigrate the Stipe win because it happened at 42 years of age. I don’t think there really is anything left for Jon Jones to accomplish.” Anik argues that Jones, at 37, is successfully defending titles in a physically brutal sport, while Mayweather wrapped up his peak years by the age of 38.

“What he (Jones) wants like that 30, 40, 50, million dollar payday, which he so deserves,” Anik added. But here’s the kicker, in boxing, Mayweather achieved those financial milestones multiple times, raising a key debate about the differences between the two sports. When Anik says Jones has “pushed himself beyond” Mayweather, how do we measure that?

From one angle, Jones’ accomplishments in MMA, dominating two weight classes and returning after a long layoff to beat a heavyweight legend places him in rarefied air. Unlike Mayweather, who retired at 38 after his 2015 bout with Andre Berto, Jones is still thriving and looking for his next big challenge at the same age. Yes, Mayweather did return in 2012 to fight Conor McGregor at 41, but that bout was more spectacle than a legacy-defining contest.

On the other hand, Mayweather’s career achievements remain unmatched in boxing. With a spotless 50-0 record and some of the highest paydays in sports history, ‘Money’ turned boxing into a billion-dollar enterprise. Jones, despite being arguably the greatest MMA fighter ever, has yet to command the kind of financial success Mayweather routinely enjoyed. Does this disparity reflect the sports themselves rather than the athletes?

Mickey Bey believes Floyd Mayweather Snr is one of the most influential trainers in boxing history. At 41, Bey says Mayweather Snr’s impact is everywhere, though few acknowledge its presence.

While Bey plans to take a few more professional fights, he is now mainly focused on training – passing along the lessons he learned from Mayweather Snr though Bey clarified that he is focused on a small precise group of the fighters since he “really can’t deal with most of these guys and  it has to be the right fit and situation.”

Among his current projects is Devin Haney, the undefeated junior welterweight star who fought just once in 2024 – a no-contest against Ryan Garcia.

Bey ranks Mayweather Snr among the greatest trainers ever.

“I think Floyd is definitely one of the top, best trainers ever. Top, top, top. Definitely in the past 40 or 50 years, I’d put him number one, honestly. That’s my opinion. I respect Emanuel Steward too – I trained under him as a teenager, and he was a genius – but Floyd Snr is something else as a teacher. He’s a true genius.”

Bey detailed the contrasting styles of Steward and Mayweather Snr, emphasizing their unique strengths.

With Emanuel, I learned balance, distance, sitting down on shots – how to hurt and finish a guy,” Bey said. “Emanuel loved knockouts; he wanted the job finished. That’s that Kronk style, aggressive but smart. Floyd Snr was more drill-sergeant strict. He’d make you do everything his way, or he’d let the whole gym know you were slacking. But he taught me things no one else could – different defensive maneuvers, counters, and combinations. To this day, I remember most of them.”

Bey commented on how modern trainers mimic Mayweather Snr’s techniques without truly understanding them.

“You see it everywhere now – people mimicking Senior’s mitt work, even in movies. But they don’t give him or Roger credit. These YouTube trainers? They’re butchering it. It looks good to people who don’t know boxing, but it’s not the same. Senior’s methods were sharp, precise, and he demanded perfection.

“Boxing is life and death. You can’t just copy someone’s style without knowing the real technique. It’s like trying to fly a plane without a license. Senior’s knowledge is the real deal, and I’m just blessed to have learned from him.”

For Bey, Mayweather Snr’s influence transcends technique; it’s about a lasting legacy.