My initial thought would be that Mayweather could surely duplicate the defensive wins that Starling and McGirt were able pull off against Brown. However, unlike Starling and McGirt, I think Floyd's hand speed would allow him to tag Brown more often than even McGirt did. Eventually the frustration at missing and getting countered would force Brown to be recklessly aggressive. At that point, probably late in the fight, Mayweather could catch him with a big shot that ends the fight.
Simon was past it by time he fought McGirt. Floyd aint stopping a prime Brown. No way! Simon was way too tough. Hell Norris was taggin him at wil in thier rematch, and Brown lasted the distance. However, Floyd would outbox him. Mayweather by UD.
So you're saying a 'past it' Brown was able to brutally stop Norris? Brown was an animal in the Blocker fight right before the McGirt bout. There is no way he was suddenly past his prime in the span of 3 months. I would agree that he could no longer comfortably make 147 and that hurt in the McGirt fight. But there's no way in hell Brown was suddenly past his prime just because McGirt absolutely schooled him. I agree that a KO for Mayweather is a stretch. But I can easily see Brown getting recklessly when behind on points and Floyd catching him with a shot he never saw coming. If not, a runaway UD for Floyd without question.
I don't think Simon could have hit him clean many times, so I'd take Floyd on points as he'd steer and turn Brown around and into his punches while blocking and then countering off of Simon's attempts. 10-2 Mayweather.