August 26’s Floyd Mayweather Jr. vs. Conor McGregor bout has captured the world’s attention in a way few fights have, but while it may feel like a once-in-a-lifetime matchup, “what if” questions involving different combat sports disciplines are a 100-year-old tradition.
From spectators clamoring for a match between wrestling legend Ed “Strangler” Lewis and elite pugilist Jack Dempsey in the 1920s, to the mixed rules contests in the 1960s and 1970s that planted the seeds of MMA, fans have always been willing to line up to find out what would happen if a boxer faced off with an opponent from another fighting style.
With The Money Fight quickly approaching, let’s take a look back at the various contests that have pitted boxer against martial artist. Some of these have taken place in 56,000-seat arenas. Some have happened in smoky local theaters. All of them, however, have given an answer to the “what ifs” of the time.