What If: Sergio Martinez vs Floyd Mayweather

There was a brief window in the second half of 2007 when it would've been a viable fight. Floyd took the big money fight with Hatton and then Williams killed the fight and any serious perception that he'd beat Floyd by losing to Quintana.

Williams went on to become relevant again briefly after the Winky and first Sergio fight. But then he got starched in the rematch and shut that window.

Williams also had the HBO hype machine behind him. The fight could've happened but Williams couldn't keep it together.

 

There was no window in 2007 because Floyd owed Oscar a rematch but was allowed 1 fight prior to it taking place which was Hatton. By the time Floyd unretired Williams was campaigning at Middleweight chasing Pavlik for a fight. I've never heard of serious talks about Floyd and Paul fighting should both win their next fights. Floyd was never interested and it would have been a fairly easy fight to make because both were Haymon advised fighters.