Dream Matchups Between Current Boxing Stars and Past Greats

Debating hypothetical matchups between current stars and all-time greats has always been a staple of conversation for sports fans. It's true in every sport. 

But in boxing, due to the existence of weight classes, the conversations are more nuanced than they are when it comes to sports like basketball or football, where contemporary stars dwarf the athletes from even two or three decades ago. 

Indeed, for a list like this, the all-time greats invariably get the edge. Few top stars at any given moment have managed to establish their claim to permanent greatness. 

Please note that in most cases, the all-time great I've selected is not necessarily the fighter I view as the best ever at that weight. I've chosen from the legends based upon who I think would make for a compelling matchup. 

I've also included Manny Pacquiao and Floyd Mayweather as "current stars." They may both have announced their retirements, but they've also both been active within the past year. And this is a much more interesting read if they are taken into consideration. 

Miguel Cotto vs. Wilfred Benitez

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When Miguel Cotto won the middleweight title from Sergio Martinez in June 2014, it made him the first four-division champion ever from Puerto Rico. Many fans, especially younger ones, no doubt view Cotto as the top boxer ever from the tiny island nation. 

As far as I'm concerned, though, he needs to get in line behind Wilfred Benitez. Benitez's career was somewhat overshadowed by his contemporaries, the "four kings" of Ray Leonard, Marvin Hagler, Tommy Hearns and Roberto Duran. 

But it would be more fair to regard Benitez as the fifth king. At 17, Benitez became the youngest world champion in history, when he defeated the very skilled veteran champion Antonio Cervantes by split decision, to capture the WBA light welterweight belt. 

Benitez added the WBC welterweight title to his resume by age 20. He added the WBC 154-pound title at 21. 

Benitez lost by Round 14 TKO to Leonard in a very competitive fight. He defeated Duran and lost to Hearns by majority decision. 

Cotto is a well-rounded boxer who could really bang at 140 and 147 pounds. Benitez was a brilliant defensive fighter, with tremendous heart and decent power. This would have been a classic fight. 

Guillermo Rigondeaux vs. Wilfredo Gomez

For boxing fans who have grown weary of Guillermo Rigondeaux's fights, which are marked by defensive brilliance but an overall lack of action, Wilfredo "Bazooka" Gomez might very well provide the perfect antidote. 

If Rigo rates as one of the slickest super bantamweights of all time, Gomez is the most destructive. Indeed, Gomez never lost a fight at 122 pounds. After drawing in his first professional fight, he knocked out every man he ever faced in the super bantamweight division.

Rigondeaux has demonstrated an uncanny ability to remove the fangs from very dangerous offensive fighters. But he hasn't faced anyone like Gomez.

The Puerto Rican legend could cut off the ring and turn it into a phone booth. He threw smothering flurries to the body and head and could end a fight with a single punch from either hand. 

Roman Gonzalez vs. Pascual Perez

Roman Gonzalez is one of the few active stars on this list who is at least approaching the status of an all-time great. He is a three-division world champion and has knocked out 38 of 45 opponents as a professional. 

Of all the great flyweights from history, Pascual Perez would have been the most exciting matchup for Gonzalez. The Argentine sensation was an Olympic gold medalist in 1948 and ruled the 112-pound class for nearly six years, from 1954 until 1960. 

Even for a flyweight, Perez was small, standing just 4'11". Like Gonzalez, he was a relentless pressure fighter who left his opponents very little space to counter or gather their own bearings.

Perez also shared Gonzalez's ability to end a fight inside the distance. The tiny slugger is a member of the select group of professionals with more than 50 career knockouts.

Terence Crawford vs. Julio Cesar Chavez

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Julio Cesar Chavez was among the biggest boxing stars of the 1980s and 1990s. He's arguably the greatest Mexican fighter of all time. 

He also has a great case for being the best light welterweight who ever lived. 

Terence Crawford is the top-rated 140-pound fighter in the world right now. He very much looks like an emerging superstar. 

He hasn't defeated a single Hall of Famer, yet. But stylistically, he's an interesting potential matchup with Chavez.

There are some basic similarities between Crawford and Meldrick Taylor, a fighter who was beating Chavez when the legend caught up to him and knocked him out with just a single second remaining in the fight. 

Andre Ward vs. James Toney

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James Toney fought as recently as last August, losing a 10-round decision to 9-3-1 heavyweight Charles Ellis. But that 47-year-old Toney is not the fighter I am talking about here. 

For this list, I'm talking about James Toney as he was a generation ago, when he fought at 168 pounds. At that weight, Toney was an all-time great. 

Toney has still never been knocked out and has had the punching power to trade shots with much bigger men, as a very overweight, over-the-hill heavyweight. 

Andre Ward cleaned out the super middleweight division between 2009 and 2011 while barely losing a round. But he didn't face a fighter anything close to what Toney was in his prime.

Ward has always been great at pressuring opponents and making it rough for them on the inside. But Toney was always extremely comfortable fighting on the inside, bobbing away from punches and then countering with fight-ending shots.

Ward vs. Toney would be a stylistic explosion. 

Saul Alvarez vs. Terry Norris

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Right now, a potential fight between Saul Alvarez and Gennady Golovkin is the sport's current leading soap opera. Alvarez vacated the WBC middleweight title last week. It is unclear whether he will remain at super welterweight, instead of making what would seem like a natural move to middleweight. 

So for a list like this, it seems only natural to speculate on a fight between Canelo and "Terrible" Terry Norris, a three-time champion at 154 pounds during the 1990s. Norris was the first big star trained by Abel Sanchez, who currently trains Golovkin. 

Norris first became a world champion with a stunning knockout of John "The Beast" Mugabi in 1990. He is perhaps best remembered for stopping an aging Ray Leonard in 1991. 

Norris was knocked out in his prime by Julian Jackson and Simon Brown, so he could be vulnerable to big punchers. But he was also a very rough, dangerous fighter, with good technical skill. He was the type of fighter who would make for a very exciting bout with Canelo. 

Gennady Golovkin vs. Marvin Hagler

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Marvin Hagler is arguably the greatest middleweight champion in history. In fact, as a fan who grew up in New England in the 1980s, that's exactly the argument I would make, that Marvelous Marvin is the greatest 160-pounder who ever lived. 

Gennady Golovkin has yet to assemble a resume that puts him anywhere close to that debate. Still, the parallels with Hagler's career are obvious, and so they make for an interesting "what if?"

Like Golovkin, Hagler was a dangerous puncher-boxer and one of the most avoided fighters of his era. Both men had been campaigning for years by the time they finally emerged as top box-office draws. 

Golovkin fought his entire career as a middleweight, never moving up. Like Hagler, GGG seems determined to establish his own era of complete dominance over the division. 

Sergey Kovalev vs. Harry Greb

Harry Greb is most well-known today as a middleweight. He's routinely mentioned in debates over the best 160-pound fighters of all time. 

But Greb was a world champion at light heavyweight as well, and also deserves status as an all-time great at 175 pounds. Fighting in that division, Greb was the only man to ever defeat Gene Tunney.

Known as "The Pittsburgh Windmill," Greb was a relentless, attacking fighter. Toughness is taken for granted in professional prizefighting and the standards for toughness were even higher in Greb's era. 

But even by the measuring stick of his time, Greb's toughness was legendary. His mean streak in the ring was legendary as well. 

That's what makes him such an intriguing hypothetical matchup for Kovalev. Kovalev is quick to smile outside the ring, but absolutely sadistic inside of it.

Greb was famous for enjoying a good time out on the town. But he seemed to enjoy beating up other men more than anything else in life. 

Manny Pacquiao vs. Roberto Duran

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In a sense, Manny Pacquiao has been the Roberto Duran of this generation. Both men were born into grinding poverty in destitute countries, only to one day become wealthy superstars in the United States. Both men electrified crowds with their offensive approach and became transcendent heroes in their home countries. 

While Pacquiao started his professional career at flyweight and Duran won a world title at middleweight, they were both at their best at around the same weight. Pacquiao was an outstanding featherweight and could have been a great lightweight, if he had stayed in the division for any length of time. 

Duran was arguably the greatest lightweight who ever lived. 

Old-school fans who are my age will insist that Duran would have been too technically sound and mentally nasty for Pacquiao. Younger fans might disagree and point to Pacquiao's greater speed. 

But there's no doubt that this would have been a tremendous bout. 

Floyd Mayweather Jr. vs. Henry Armstrong

Of all the potential historical matchups for Floyd Mayweather, Henry Armstrong is always the one that has intrigued me the most. Given his claim to status as the best ever, it's natural to compare him to Sugar Ray Robinson. 

But I don't even view that as a fair comparison. Robinson was a big welterweight and wasn't exactly small when he fought as a middleweight. Mayweather began his career at 130 pounds. He dominated at welterweight and junior middleweight, but he did it while walking around at about 150 pounds. 

Armstrong was much closer in size to Mayweather but also had Mayweather's ability to out-class larger fighters. At one point in the late 1930s, Armstrong held the world title at featherweight, lightweight and welterweight at the same time. 

This was an era with one champion and no half weight classes. So Armstrong was the only champion from 126 pounds to 147. Today, 20 or more "world champions" at any given time might rule over that same stretch. 

For stylistic reasons, this bout is particularly compelling. Hurricane Hank was a whirlwind offensive fighter, attacking in overwhelming flurries. Mayweather is among the best defensive fighters who ever lived.