Benn, who held gold at middleweight and super-middleweight, shared his thoughts with The Sun. He's got a lot of praise for Calzaghe's career and skills.
"Old timers will tell you [Calzaghe] would never have lived with Roberto Duran, Sugar Ray Leonard, Marvin Hagler or Tommy 'Hitman' Hearns. I disagree — Joe would have beaten them all. How many fighters would love to finish with a record like Joe's? Outside of Wales, I don't think he got the recognition he deserved. Forty-six fights unbeaten is a heck of an achievement. I don't think we will ever see his like again."
Calzaghe's career was truly remarkable. He held world honours at 168lbs for over a decade. The Welshman scored big wins over Mikkel Kessler and Chris Eubank Sr at super-middleweight. He then moved up to light heavyweight and defeated Bernard Hopkins and Roy Jones Jr.
Duran, on the other hand, was a four-division world champion. He won titles at lightweight, welterweight, light middleweight and middleweight. He even competed as high as 175lbs. Duran was part of the 'Four Kings' along with Sugar Ray Leonard, Marvin Hagler, and Thomas Hearns. These four had epic battles with one another throughout the 1980s.
Benn thinks Calzaghe didn't get the recognition he deserved outside of Wales. He points to Calzaghe's perfect 46-0 record as a "heck of an achievement" that might never be matched.
This fantasy matchup between Calzaghe and Duran has been a hot topic among boxing fans for years. Other big names in boxing have also weighed in on how this fight might go. Carl Froch is another fighter who's often mentioned in these hypothetical matchups with Calzaghe.
These kinds of predictions and debates keep boxing fans talking and show how much respect there is for fighters across different eras.