10 Best Fantasy Fights Between Retired Greats and Boxing's Top Current Stars

Kevin McRae@@McRaeWritesFeatured ColumnistAugust 26, 2014

10 Best Fantasy Fights Between Retired Greats and Boxing's Top Current Stars

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    As many Americans gear up for fantasy football season, it seemed that the timing was right to delve into boxing's fantasy realm.

    If you're a hardcore fan, the odds are pretty good that you've engaged in at least one discussion, debate or argument over what would happen if current star "A" faced star of yesteryear "B."

    And if you're like me, these discussions often end with a flipped coffee table and little agreement on the subject matter.

    Here we present 10 hypothetical matches between some of boxing's biggest names in 2014 and their counterparts in eras gone by. 

    For all matches we assume a weight division, generally where each fighter was at their best, analyze strengths and style and make a prediction.

    Each contest assumes that both fighters were in their physical primes, and, as always, you're free to disagree, dissect, yell, complain and tear the analysis apart as you will in the comments section.

    Let the debate begin!

Bernard Hopkins vs. Marvelous Marvin Hagler (160 Pounds)

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    Hopkins' Style and Strengths:

    Bernard Hopkins began his career as a power-puncher and gradually developed into the cagey technician we know and love today. He’s soaked in, literally, every lesson from four decades in the ring, and he knows all the tricks in the book.

    Hopkins knows where he is in the ring at all times, creates angles and sets traps to throw his foe off his game. Even today, at 49 years old, he remains virtually impossible to hit with two clean punches in a row, and few fighters are better at frustrating an opponent.


    Hagler's Style and Strengths:

    Much like Hopkins, Marvelous Marvin Hagler was a no-nonsense dude inside the ring. He was a natural southpaw, but he packed devastating power in both of his fists, and that allowed him to switch between orthodox and southpaw stances.

    He was an intimidating guy to look across the ring and see staring back at you. Cutting off the ring was his speciality, and 52 of his 62 wins came inside the distance, often in vicious fashion. Hagler was also a tremendous counterpuncher and fought with a high level of activity.



    Middleweight is one of boxing’s glamour divisions, and Hopkins and Hagler are two of the very best to ever lace up the gloves. It’s easy to make the case for either man, but the edge here narrowly falls to Hopkins because of his ability to frustrate his opponents.

    B-Hop is a master of setting traps and making his opponent pay, and Hagler, for all his offensive firepower, was the type of fighter who could be frustrated and lose his mental focus. Hopkins would box him, slip punches and take a competitive decision by making use of his superior defense and mental toughness in the ring.

    Hopkins by Decision

Wladimir Klitschko vs. Muhammad Ali

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    Klitschko's Style and Strengths:

    Wladimir Klitschko is a true super-heavyweight fighter who makes good use of his size, range and piston-like jab. His length and size make him a hard nut to crack, and getting on the inside to land shots on his sometimes-suspect chin is no easy task.

    Klitschko uses every bit of his size in the ring. He finds range with his jab—also using it to disrupt a foe’s rhythm—setting up his powerful right hand, and he likes to lean on his opponent to further wear him down. All that combines to create many quick nights of work for the current heavyweight champion.


    Ali's Style and Strengths:

    Muhammad Ali, known as The Greatest, owned the heavyweight crown on three separate occasions and is widely considered not just among the greatest big men in history but the greatest fighters in any weight class.

    He had stupefying speed and reflexes and was highly mobile, often dancing around his opponents and striking them with quick shots from different angles. It was virtually impossible to corner him, and getting him into uncomfortable spots was a rare occurrence.


    Klitschko is a heck of a fighter, but he’s presided over a very weak crop of heavyweights. There are no Joe Frazier’s or George Foreman’s in this bunch, and Ali had to navigate the division at times when every fight was tough.

    Ali has the speed and movement necessary to get inside of Klitschko’s tight defensive guard. His mobility would become a factor for Klitschko, who has had a few conditioning issues during his career, wearing him down. Ali has the power to ding his chin, likely with a counter right hand that would land square on Klitschko’s chin over his jab and end the fight.

    Ali by Knockout

Floyd Mayweather Jr. vs. Sugar Ray Leonard (147 Pounds)

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    Mayweather's Style and Strengths:

    Floyd Mayweather Jr. is his era’s gold standard for boxing excellence. He’s won all 46 (and counting) of his professional fights, the vast majority of which he won without even being challenged, and has captured 11 world championships in five weight divisions.

    Money is a master-class technician who ranks up there with the best fighters in history at hitting and not getting hit in return. He’s most comfortable with a defensive style which allows him to use his in-ring intelligence, speed and positioning to frustrate his opponent offensively while opening him up for counter shots of his own.


    Leonard's Style and Strengths:

    Sugar Ray Leonard was a blur in the ring. His hands were so fast, and his combinations so crisp and vicious, that you were on the floor before you even knew what was coming your way. His punches came in furious bunches, and if you wanted to land a shot in return you had to walk through fire to get there.

    Leonard was borderline untouchable in his prime—much like Mayweather today, making this a matchup of defensive geniuses—defeating fellow all-time greats Roberto Duran (twice), Tommy Hearns and Marvelous Marvin Hagler during his Hall of Fame career.



    Were this fight contested 100 times, each man would snag his share of victories, but Leonard is the overall better fighter. The two men are extremely well-matched when it comes to pure technical skill, and on that front it’s a very evenly matched fight.

    But Leonard was faster, more aggressive and packed a bigger punch than Floyd. His pressure, stalking and ability to land would be the difference in the fight. Mayweather wouldn’t possess his customary speed edge in the center of the ring, forcing him onto the back foot and into the ropes. That’s where Sugar would take over.

    Leonard by Decision

Sergey Kovalev vs. Roy Jones Jr. (175 Pounds)

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    Kovalev's Style and Strengths:

    Sergey Kovalev is an absolute wrecking ball. He has great footwork, which he uses to put himself in position to attack and places tremendous physical and mental pressure on his opponents. His power, the sheer concussive force of his punches, is enough to intimidate most foes before the bell even rings.

    Kovalev is effective at bringing that power to bear, cutting off the ring and forcing engagements on his own terms.


    Jones Jr.'s Style and Strengths:

    In his prime, Jones Jr. was easily the most agile fighter in the sport, possibly of all time, and he was able to use that skill and his God-given speed to dominate the light heavyweight division. It wasn’t even close.

    Jones was a tremendous counterpuncher, popping shots from out of nowhere, hitting his opponent from angles that seemed impossible and getting away before he could react. He rarely used the jab, but he led with dizzyingly quick straight rights or left hooks, often using a fair bit of theatrics to confuse an opponent before striking.



    During his heydey, Jones could not be hit. He would move around in front of you, using his footwork to control the distance and the pace, and before you even thought of letting your hands go, you’d be popped with shots, and he’d be gone.

    Kovalev has tremendous punching power and underrated boxing skills, but it’s easy to see how Jones would take both of those weapons away from him. That’s because Jones was just that good. He would outbox, outmove and frustrate Kovalev, winning a comfortable decision.

    Jones Jr. by Decision

Andre Ward vs. Joe Calzaghe (168 Pounds)

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    Ward's Style and Strengths:

    Andre Ward is a excellent technical fighter who has seen his career largely derailed by injuries and promotional issues. When he has been in the ring, he’s been dominant, cleaning out the super middleweight division and staking a claim for pound-for-pound recognition.

    Ward is a chess player in the ring, and he has the ability to think several moves ahead of his opponent. He uses his legs to stay out of range and likes to smother his foe's attack. Versatility is the name of his offensive game, and he does everything with a high level of proficiency but doesn’t stand out in any one category.


    Calzaghe's Style and Strengths:

    Joe Calzaghe’s style was oft-criticized during his time in the sport, but it was good enough to secure him 46 wins without a defeat and a spot in the International Boxing Hall of Fame in Canastota, New York.

    The Welsh champion was an awkward southpaw fighter who had good speed and a very high punch output. His stamina and conditioning were tremendous, and most of his opponents simply couldn’t keep up with his high-volume attack. Critics of his power neglect to mention his 32 stoppage victories and the way he rearranged Jeff Lacy's face.


    Calzaghe gets a bad rap in the United States, largely because he only fought in the U.S. twice. Those two performances, however, were impressive and saw the Welsh fighter knock off a still formidable (even now) Hopkins and a past-his-prime Roy Jones Jr.

    But he also took out Mikkel Kessler—a better version than Ward faced—Sakio Bika and Lacy, the latter in ridiculously lopsided fashion. Lacy was never the same after that beating, which for all practical purposes ended his promising career. His volume would give Ward difficulty and lead him to a decision win.

    Calzaghe by Decision

Gennady Golovkin vs. Julian Jackson (160 Pounds)

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    Golovkin's Style and Strengths: 

    Gennady Golovkin has the highest knockout ratio in middleweight history. Allow that to properly sink in for a second. The Kazakh bomber has knocked out exactly 90 percent of the men who have been unfortunate enough to step into the ring and feel his wrath.

    Golovkin is a smooth operator, moving fluidly around the ring, cutting off his opponents and unleashing blistering combinations to the body and head. He mixes his punches well and has devastating power in both hands.


    Jackson's Style and Strengths: 

    Julian Jackson, a former junior middleweight and middleweight world champion, knows a thing or two about being a big puncher. The U.S. Virgin Islands-born slugger was ranked No. 25 by The Ring Magazine in a 2003 listing of the 100 greatest punchers of all time.

    Jackson’s 1990 knockout of Herol Graham to win the vacant WBC Middleweight Championship was sudden, scary and has to be seen to be believed. That type of one-punch stopping power defined his career, and it made him one of the most dangerous punchers in boxing history.



    A matchup of two absolutely devastating middleweight punchers? Why not, right? Golovkin is clearly the more refined of the two; he's stronger technically, but he's never tasted the type of power that Jackson could bring to a fight.

    This one would be fun for as long as it lasted, but that wouldn't be very long at all. Jackson could land a mother of a punch, but he suffered all six of his career defeats inside the distance. GGG, with his ability to cut off the ring and take a punch, would zero in and blast away.

    Golovkin by Knockout

Juan Manuel Marquez vs. Alexis Arguello (135 Pounds)

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    Marquez's Style and Strengths:

    Juan Manuel Marquez is best known as an aggressive and explosive counterpuncher, but he does plenty of other things well too. He has game-changing power, and you’ll find few fighters who are tougher or more resilient.

    Marquez can never be counted out. He was down three times in the opening round of his first fight against Pacquiao, rallying for a draw, and stopped his Filipino rival with a missile right hand with his nose badly broken and gushing blood. He has the will of a fighter, and you can’t teach that.


    Arguello's Style and Strengths:

    The late Alexis Arguello, El Flaco Explosivo, the explosive thin man, was everything the name would seem to indicate. A freakishly tall fighter in the lower weight classes, the Nicaraguan was blessed with tremendous power and in-ring smarts.

    Arguello was a boxer-puncher who moved quickly across the ring behind his left jab, using it to set up his crunching left hook and straight right hand. He was a surgeon, systematically finding weaknesses, breaking down his foe and emphatically going in for the kill.



    This is an extremely tough call, but Arguello would probably have a slight edge over Marquez at 135 pounds. That’s based on pure feel for the fight, and you can just as easily argue the other side.

    Arguello was a bigger puncher, and Marquez has been down before. His resilience saved him against Pacquiao in their first fight, but El Flaco Explosivo is a significantly harder puncher. If he hurt Marquez, he’d likely have been able to close out the show.

    Arguello by Knockout

Brandon Rios vs. Arturo Gatti (140 Pounds)

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    Rios' Style and Strengths: 

    Brandon Rios is one of those guys who just loves to fight. He’s a straight up banger and just as likely to have a big smile on his face after eating a shot as landing one.

    There isn’t a whole lot of finesse to Bam Bam’s game. He’s a high-activity brawler with good power—even game-changing power at times, just ask Mike Alvarado—who’s going to stalk, throw a ton of punches, eat a ton of punches and enjoy every second of it.


    Gatti's Style and Strengths: 

    Arturo Gatti was often referred to as a blood-and-guts warrior during his career, and the late Hall of Famer earned every bit of that title. He began his career as a pure brawler, coming forward, swallowing a ton of punches in order to land a few of his own.

    Gatti was extraordinarily tough and resilient—sometimes too much so—and he always seemed to do his best when the odds—grotesque swelling or blood gushing from his always troublesome eyes—were seemingly insurmountable.



    Gatti was best known for his brawling days, but he also had some decent boxing skills. Those manifested themselves mostly after his legendary first fight against Micky Ward, and they would give him an advantage over the largely one-dimensional Rios.

    By being the boxer-puncher, to Rios' puncher skills only, Gatti would be able to hold him off for a decision victory in a fight filled with bursts of high-octane activity.

    Gatti by Decision

Miguel Cotto vs. Julio Cesar Chavez (140 Pounds)

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    Cotto's Style and Strengths: 

    At his best, Miguel Cotto is a pressure fighter who loves to zero in on the body with vicious, thudding hooks before taking his attack upstairs. He stalks his prey, softens it up and then goes in for the kill when he senses blood in the water.

    Cotto is very methodical in the ring, and he doesn’t throw more punches than necessary. But that doesn’t mean he isn’t a fighter. The Puerto Rican legend is a warrior in the truest sense of the word, and he possesses tremendous mental and physical toughness.


    Chavez's Style and Strengths:

    Julio Cesar Chavez is widely considered to be the best Mexican fighter in history, and that puts him atop an extensive list of great warriors and champions. In the ring, he redefined what it meant to be a pressure fighter, using his intelligence and a relentless offensive attack to overwhelm his foes.

    His left hook to the liver was a murderous money shot; often it was enough on its own to finish a fight. If not, Chavez was more than happy to take his attack upstairs and just grind you down.



    Chavez would be too much for Cotto in a brutal war. 

    The pace that the Mexican would set would be all wrong for Cotto, who prefers fighting at a more deliberate tempo, and he would grind him down, mark him up and stop him on an accumulation of punishment in the late rounds of a vicious contest. Think the first Antonio Margarito fight but with everything conclusively on the up and up.

    Chavez by Knockout

Manny Pacquiao vs. Aaron Pryor (140 Pounds)

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    Pacquiao's Style and Strengths:

    Manny Pacquiao was a force of nature in his prime. He would storm across the ring, unleash punches in bunches and absolutely cut through his opponents.

    His speed was his primary asset, backed by a tremendous straight left hand. Pacquiao never really had massive one-punch power—his fight with Ricky Hatton being an obvious exception—but most of the damage came from opponents not seeing the shots coming before it was too late, drastically amplifying their force.


    Pryor's Style and Strengths:

    Aaron Pryor ended his career with a 39-1 record with 35 of those wins coming inside the distance, and personal struggles probably prevented us from seeing how truly great he could’ve been.

    The Hawk was a relentless puncher who seemed to have his hands moving for every single tick of every single round. The guy just never stopped throwing punches, and all of them had mean intentions. His two wins over Arguello—the first was a legend-making bout for both men—are easily the best of his career.



    Pryor sported a perfect 11-0 record in title fights with 10 of them ending via knockout. Those are some very impressive numbers, but short of Arguello—who in fairness was an all-time great—The Hawk didn't face an overall high level of opposition. 

    What we have here is a match of two all-action fighters—the definition of the concept—that would swing on who could overwhelm the other first. It wouldn't be surprising to see both men hit and have to come off the deck in this fight, but Pacquiao has a better chin and, knockout rate be damned, a bigger punch. He takes it narrowly on points.

    Pacquiao by Decision