Five fantasy boxing bouts with clear-cut winners

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Danny Howard

September 15th, 2021

Fantasy fight aficionados, this one is for you. We've journeyed deep into the reaches of our imagination and have come up with the five most enticing fantasy fights of all time, including an epic heavyweight clash that boxing fans have been dreaming about for more than 30 years.

5. Manny Pacquiao vs. Julio Cesar Chavez

Manny Pacquiao: 62-8-2 
Julio Cesar Chavez: 107-6-2

One of the most salacious fantasy fights everyone seems to ask about is a war between Pacquiao and Chavez. Both were known for their punching power and history of violence, but had we seen a prime version of either man at 130, 135, or even 140, it would be an easy night for Pacquiao. Chavez was always a gritty battler that could never be counted out, but Pacquiao’s speed as well as his awkward attack would have eaten Chavez alive.

Winner: Manny Pacquiao

4. Andre Ward vs. Joe Calzaghe

Andre Ward: 32-0
Joe Calzaghe: 46-0

Ward came to prominence at 168 after Calzaghe left the division to win a light heavyweight title and retire, so it's only natural that many wondered how a bout between the two would go. Calzaghe’s high volume attack helped him notch 21 defenses of his title, but Calzaghe would have been a nobody against the sharper, rougher Ward. Ward was the master of adjustments and would be a stylistic nightmare for the busy Calzaghe. Though a lot of people don’t seem to like Ward, he’d walk all over Calzaghe in a theoretical bout.

Winner: Andre Ward

3. Gennady Golovkin vs. Marvin Hagler

Gennady Golovkin: 41-1-1
Marvin Hagler: 62-3-2

Golovkin may go down as one of the best middleweights ever and is a beloved favorite, making him a natural fantasy foil for Hagler. As good as Golovkin is, there is nothing the capable Kazakh has in his arsenal to trouble the tricky and durable Hagler. If Hagler could take flush shots from Thomas Hearns and not go down, Golovkin has no chance of hurting him. This would be fun to watch, but Hagler would win every time.

Winner: Marvin Hagler

2. Floyd Mayweather Jr. vs. Sugar Ray Leonard

Floyd Mayweather Jr.: 50-0
Sugar Ray Leonard: 36-3-1

Mayweather’s boasts of being "The Best Ever" has often put him in almost endless debates against other welterweights, namely Leonard. As good as Mayweather was, there is no way he would be able to flummox a stronger, faster, and equally skilled fighter such as Leonard. Whereas Mayweather had the perfect record, Leonard was practically the perfect welterweight and had the boxing IQ to avoid Mayweather’s traps and counters. Giving Mayweather the benefit of the doubt, he would be competitive in a clear losing effort against the great Sugar Ray.

Winner: Sugar Ray Leonard

1. Mike Tyson vs. Muhammad Ali

Mike Tyson: 50-6 (2 no contests)
Muhammad Ali: 56-5

Perhaps the most debated fight of this, or any generation, the Ali/Tyson bout is also the easiest to assess. Simply put, there is no version of Tyson that could ever beat Ali. Ali fought better fighters than Tyson and had an unshakable will to win; the exact thing that compromised Tyson throughout his career. The iconic status of both men ensures that this debate is seemingly endless, but a mythical matchup between the two would be a disappointing affair as Ali would toy with Tyson before stopping him.

Winner: Muhammad Ali