Floyd Mayweather and the Top 20 Historical Fighters We'd Love to See Him Face

The best sports bar arguments are always cross-generational affairs—debates over how athletes from different historical eras match up. Johnny Unitas vs Joe Montana vs Tom Brady. Oscar Robertson vs Magic Johnson vs Kobe Bryant.

Boxing, with its one-on-one competition and weight classes, lends itself to these discussions better than most sports. And trying to rank the greats from different eras against each other is a big part of boxing lore.

Nobody understands this better than Floyd Mayweather Jr., a boxing prodigy who grew up in the sport, with a contender for a father and a world champion for an uncle. As Mayweather enters the last years of his career still undefeated, he is hungrily eyeing his spot on the list, publicly making his case as the greatest of all time.  

That's a tough argument to make for any fighter, undefeated or not. And Mayweather's resume is frankly less than overwhelming.

Of the three best opponents on his record, two of them, Shane Mosley and Oscar De La Hoya, were clearly over the hill when Mayweather beat them. Juan Manuel Marquez, long in the tooth himself at the time of their fight, was a perfect matchup for Mayweather, a fellow counter-puncher, but slower and smaller.

Still, you would have to be deluded by Mayweather hatred to deny that he is one of the best of his generation, just like the rest of the fighters on this list. 

Willie Pep

Willie Pep, 229(65)-11(6)-1, is widely regarded as the greatest defensive fighter who ever lived. The oft-repeated legend about "Will o' the Wisp" is that he once won a round without throwing a single punch.

In 1999 the Associated Press named Pep the greatest featherweight of the 20th century and the number five boxer over all. 

As great as Pep was, he probably would have been too small to execute his game plan effectively against Mayweather. At 5'5", he was a natural featherweight and never fought higher until the very end of his career. 

Sandy Saddler

Sandy Saddler, 144(103)-16(1)-2, was Willie Pep's great rival. Between 1948 and 1951 they met four times, with Saddler winning three by knockout and losing one by unanimous decision. This was perhaps the premier series in the lower weight classes during the sport's golden age. 

Pep had been in a plane crash the year before he faced Saddler for the first time, and boxing experts who followed his career agree he was never quite the same afterwards. Nevertheless, knocking out the great "Will o' the Wisp" three times has to rank among the greatest accomplishments in the history of the featherweight division.

Saddler was a bit more slender then Mayweather, but he would have been a tough matchup for "Money May." He was a tough matchup for everyone. Saddler was regarded as one of the sport's roughest fighters during a brutal, rough and tumble era. 

If Saddler had deliberately headbutted Mayweather, a la Victor Ortiz (and he sounds like the kind of fighter who might have done just that), you can be damned sure he wouldn't have tried to hug and make up afterwards.

My opinion is that Mayweather would ultimately have the defensive skills and counter-punching ability to handle Saddler. Still, Mayweather has never faced a skilled and relentless boxer-brawler of Saddler's ability.   

Flash Elorde

Flash Elorde, 87(33)-27(4)-2, is on the short list with Manny Pacquiao for the greatest Filipino fighter of all time. Like Pacman, Elorde was a southpaw. 

He exploded onto the international boxing scene in 1955 when he won a 10-round unanimous decision over Sandy Saddler in a non-title fight. Elorde was winning the rematch five months later when Saddler stopped him by TKO in the 13th due to a cut over the eye.

You can watch the full fight on Youtube, starting with the link here. It is a thriller, with the somewhat past-his-prime Saddler pulling out every stop to retain his title, at times committing outright fouls. By the late rounds he was using his forehead more like an NCAA wrestler than a boxer.

Mayweather would have about three inches in height on Elorde and four inches in reach—a decisive advantage for a counter-punching wizard. 

Azumah Nelson

"The Professor" Azumah Nelson, 39(28)-6(1)-2, is one of my favorite all-time fighters. He was among the greatest featherweights and jr. lightweights of the 1980s and early 1990s.

Nelson is a national hero in his native Ghana, and has dedicated much of his post-boxing career to improving education in the coastal African country. The sport of boxing has had few ambassadors better than Nelson.

For all the reasons I love Nelson, I find the bling-bling, baby-mamma-beating Mayweather very hard to stomach. Just the same, you can't argue with greatness.

Nelson was a great man in AND out of the ring, but I have to be honest, and I just don't see how he could have handled Mayweather. When he went up to lightweight to challenge Pernell Whitaker he lost a competitive, but decisive, unanimous decision.   

Joe Gans

You've got your Hall of Famers, your all-time greats and your legends. And "The Old Master" Joe Gans was all of these.

But beyond those superlatives, you've got your folk heroes—the mythical figures from the nearly lost early days of the modern sport of boxing. And more than anything else, Joe Gans exists in the sport's memory now as a folk hero. 

The Ring's founding editor Nate Fleisher ranked Gans as the greatest lightweight of all time. Gans' boxrec.com record is 145(100)-10(5)-16, but as impressive as that is, it doesn't tell half the story. At the turn of the last century when Gans fought, boxing was a quasi-legal affair and only a fraction of bouts were even recorded as "Newspaper Decisions." 

Boxing fans frustrated by the Pacquiao-Mayweather impasse should go read up on a guy like Joe Gans. Then you will really be depressed by the sorry state our world has fallen into. In Joe Gans' day, not only did the very best guys in a weight class fight each other, often again and again and again, but they often fought far outside of their weight class. 

I won't even venture a guess about what would have happened if Pretty Boy had ever fought Joe Gans. The little bit of video linked here is about as much film as I've seen of him. 

But I will say this: To be an all-time great in Joe Gans' day, you had to battle through a level of competition and adversity that Floyd Mayweather Jr. can only imagine. 

Gans' contemporaries and near-contemporaries could not rave enough about him. From his boxrec.com biography:

"

 Sam Langford deemed him the greatest boxer of all time^{[citation needed]}; Benny Leonard, who is generally considered the next best lightweight in history, idolized Gans^{[citation needed]}; and Bob Fitzsimmons--the first of only two fighters in history to capture undisputed, lineal world titles in three of boxing's eight traditional weight divisions--called Gans the cleverest fighter he'd ever seen^{[citation needed]}. Abe Attell gave his opinion that "Joe Gans was the greatest lightweight that ever entered a ring. In his prime no fighter of his weight was his equal." Baltimore American, August 15, 1910.

"

If there is some portion of the afterlife dedicated to allowing the greatest fighters of all time to have at it (and I frankly believe that there is), then you can rest assured that The Old Master will be waiting at the front of the line to shake Mayweather's hand and then punch him in his mouth. 

Benny Leonard

Born in 1897 on Manhattan's lower east side, Benny Leonard should be viewed a kind of ultimate New York City icon. He was the first native-born New Yorker to win a world title.

Leonard, 90(70)-17(5)-7, emerged from the brutal New York City club fighter scene as a largely self-taught virtuoso. His nickname was "The Ghetto Wizard."

A Mayweather-Benny Leonard clash would be a matchup of master tacticians. As with many of the men on this list, you need to discount the win-loss record. Almost all of Leonard's losses came early in his career, when he was learning his craft and fighting every week or two for 20 bucks a pop if he was lucky. 

Leonard had a run of dominance in his prime that compares more than favorably to Mayweather's own career. And he never took any two-year breaks to screw around with the clown show of pro wrestling. 

I consider Leonard one of the really interesting figures in the sport's history. Still, I ultimately have to give the nod to Mayweather, the larger, modern athlete.  

Carlos Ortiz

If Benny Leonard was the iconic New York City lightweight of the World War One era, Carlos Ortiz, 60(30)-7(1)-1, held that distinction for the 1950s and 60s. I've seen him in person a few times in recent years; to a boxing fan, that's like seeing Micky Mantle or Willie Mays.

Ortiz was among the first light welterweight champions, but that title meant relatively little in the late 1950's. After dropping that belt to Dulio Loi in 1961 he dropped down in weight and for the better part of the decade he ruled as the lightweight champion of the world. 

Carlos Ortiz was precisely the type of fighter I imagine Mayweather might have trouble with an aggressive, straight-ahead fighter with decent head movement, who can bang the body.

Again, I'm going to have to insist that Mayweather patrons refrain from trying to compare Mayweather's famed "O" to Ortiz's seven career losses. Floyd Mayweather Jr. has the talent and ring intelligence to be a great in any era, but if you think he would have come through Ortiz's run undefeated, fighting that level of competition that often, then you must have drunk some Kool Aid somewhere along the line.

Mayweather's haters like to pretend he's some kind of sissy, but the fact is, he has always reacted to pressure with manly aplomb. An in-his-prime Carlos Ortiz would probably be a tougher challenge than Mayweather has ever faced, but ultimately I feel like he would simply have too much finesse for Ortiz.  

Alexis Arguello

Alexis Arguello, 77(62)-8(4), had one of the greatest nicknames in the sport's history, "El Flaco Explosivo," or The Explosive Thin Man. He was a power puncher who could finish fights quickly. 

Thinking about this fight makes me think about Mayweather's fight with Diego Corrales, another tall, thin fighter with big punching power. A lot of people expected that to be a tough matchup for Mayweather.

It wasn't. 

Well, Corrales was no Alexis Arguello, and Arguello most certainly would be a tough fight for Mayweather. But ultimately I think he would be too quick and slick for the Nicaraguan great. 

Roberto Duran

For my money, Roberto Duran, 103(70)-16(4), vs. Mayweather is one of the tougher fights on this list to pick.

Mayweather's expert counter-punching would create problems for "El Manos de Piedro," but I have doubts about whether or not Mayweather would be able to land enough punches to discourage Duran's relentless forward pressure. 

Under trainer Ray Arcel, Duran developed a pretty tricky defense to complement his overwhelming offense. My own opinion is that he would be able to work his way inside on Mayweather, attack his body, slow him down and beat him late.  

Julio Cesar Chavez

Julio Cesar Chavez, 107(86)-6(4)-2, actually stopped Floyd Mayweather's uncle Roger in 10 in May of 1989. Needless to say, beating the nephew would be a completely different matter.

To me this matchup looks a lot like Duran-Mayweather, except that I don't think Chavez has Duran's defensive abilities.

It also looks a lot to me like Chavez-Pernell Whitaker, a fight that was ruled a draw, but was widely considered a victory for Whitaker (Sports Illustrated put Whitaker on the cover the week after the fight, with the one-word headline "Robbed"). 

But Chavez would take two or three to deliver one, and his one was always vicious when it landed. So there's a good chance this fight ends up like Chavez-Meldrick Taylor.

I think Mayweather would be able to stay away from Chavez and beat him by decision. Still, this is Julio Cesar Chavez, J.C. Superstar. As a fan who grew up in the 1980s, it's tough for me to pick Mayweather over him.  

Salvador Sanchez

Salvador Sanchez is one of boxing's biggest "what ifs." When he died in a car crash at age 23, he had already compiled a professional record of 44(32)-1-1 and has established himself as a dominant featherweight champion. It seems obvious to me that more world titles—at higher weight classes—would have been waiting for him had he not died. 

Sanchez was an explosive two-fisted puncher, a complete fighter who could pressure an opponent and also aggressively counter-punch. 

He had the speed to match Mayweather, and I think his more aggressive style would have won him rounds with the judges.

Based on the film I've seen of Sanchez, I think he is precisely the kind of fighter who would be able to beat Mayweather. 

Dulio Loi

Dulio Loi, 115(26)-3-8, was perhaps the greatest fighter to ever come out of Italy and one of the first junior welterweight champions, a title he took from the great Carlos Ortiz. 

Loi was a short, stocky fighter who attacked the body ferociously. I have seen very little footage of him, but based on what I have seen, I have to believe that Mayweather would have been able to control the distance against him with his jab and footwork, safely sniping from a safe distance.

Pernell Whitaker

If Willie Pep truly was the greatest defensive boxer of all time, then "Sweet Pea" Pernell Whitaker, 40(17)-4(1)-1, has got to rank as a pretty close second place. 

This was one of the first matchups I thought of when I first contemplated this list. What makes it intriguing to me is that I am pretty sure Whitaker could have out out-slicked Mayweather. "Pretty Boy" would have been thrust into the very unfamiliar role of being the one who needs to turn it ugly. 

I believe Whitaker at his best would have beaten Mayweather, but I might have a generational bias. 

Barney Ross

Barney Ross, 72(22)-4-3, was one of the dominant light and welterweight fighters of the 1930s. He retired after dropping his welterweight title to Henry Armstrong in 1938 and later enlisted in the Marine Corps at age 32. He won the Silver Star fighting at Guadalcanal. 

Ross was among the very best during a tough and competitive era. His three-fight series for the welterweight title against the larger Jimmy McLarnin was an all-time classic.

However, this might be another case where the modern athlete Mayweather would have too much of a size and speed advantage. Even as the welterweight champ, the 5'7" Ross weighed in the low 140s.

Still, Ross was the embodiment of old-school toughness. 

Wilfred Benitez

Wilfred Benitez, 53(31)-8(4)-1, was a boxing prodigy of the same order as Mayweather—the son of a boxing family who grew up around the sport. He turned professional at age 15. At 17 he became the youngest world champion in history, taking the WBA 140-pound strap from Antonio Cervantes while his high-school classmates cheered him on. 

Benitez's career went down hill fast after the early 1980s. After his brilliant start he was done as an elite fighter at a fairly young age. Looking at his career really has to make you appreciate the way Mayweather has been able to stay focused professionally on such a brutal sport for so long. 

A Mayweather-Benitez fight would excite the boxing purists, but it might not thrill the more casual fans. Benitez was the longer fighter and faced a far superior level of competition.

At his best I believe he beats Mayweather. 

Aaron Pryor

Aaron Pryor, 39(35)-1(1), was named the greatest junior welterweight of the century by the Associated Press in 1999. The single loss in his career came years past his prime, against the obscure Bobby Joe Young, at a time when Pryor was already battling drug addiction. 

At his best, Pryor was one of the most exciting fighters of all time—a ferocious whirlwind who threw punches from every angle and level. Mayweather's style would have made for a difficult fight. I can definitely see Mayweather taking a lead against him early.

But I don't see Mayweather slowing the Hawk down for an entire fight. Pryor would have kept coming and would have eventually slowed Mayweather down. I see Pryor winning this by a late-round stoppage. 

Incidentally, Pryor appears to have very much put his personal problems behind him. One of the highlights of my trip to Canastota last spring was seeing the smiling and healthy-looking Pryor riding in the back of a convertible during the "Parade of Champions."

He stood up to wave his arms to the fans shouting "Hawk Time!" as he drove by. 

Henry Armstrong

When Henry Armstrong, 150(101)-21(2)-10, fought, there were only eight weight classes. Armstrong was the world champion in three of them—featherweight, lightweight and welterweight—at the same time. 

He challenged for the middleweight title against Ceferino Garcia and came up just short, earning only a draw. Depending upon which report you read, he may or may not have been robbed. But Armstrong came that close to being the world champion in half of the sport's weight classes.

Nicknamed "Homicide Hank," Armstrong fought with the same explosive, cyclone style as the previously discussed Aaron Pryor. He was as quick as Mayweather and would have attacked him relentlessly.

I see him winning a bloody unanimous decision or else taking out Mayweather late.  

Thomas Hearns

This might be the worst matchup on the list for Mayweather.

The 6'1" Hearns, 61(48)-5(4)-1, was always Sugar Ray Leonard's toughest matchup. He was too talented of a boxer to finesse, and without Leonard's power, I just don't see how Mayweather could pull out a win against the Hitman.

If anybody on this list would have been able to simply blow Mayweather out, I think it would have been Hearns.   

Sugar Ray Leonard

Sugar Ray Leonard, 36(25)-3(1)-1, actually fought Floyd Mayweather Sr, in 1978, winning by TKO in 10. The elder Mayweather gave Leonard one of his tougher pre-championship fights.

The far more gifted son would have pushed Leonard much more than the old man did. I also think this would be a much closer fight than Mayweather-Hearns would be.

But I don't see any way possible that Mayweather could have beaten Leonard. I would rate them pretty evenly in terms of defensive acumen, but Sugar Ray had far more offensive firepower and fought a much higher quality of competition.  

Sugar Ray Robinson

If you're going to throw yourself into the argument for the greatest boxer of all time, ultimately this is the man you are going to be measured against: Sugar Ray Robinson. 

Robinson, 173(108)-19(1)-6, is the man for whom they invented the "greatest pound-for-pound" label. He had blazing foot and hand speed and explosive punching power in both hands. He fought during perhaps the most competitive era in the sport's history and he dominated. 

Robinson had some of his greatest moments in the middleweight division, so this is probably something of a size mismatch for Mayweather.

But based on the hours of film I have watched of Robinson over the years, it is a skill mismatch, too. Sugar Ray could do everything Mayweather could do and much more.