Holmes by UD Bowe had issues vs fighters who fought him at range or fighters with good jabs both things Holmes excels at. Someone in this thread mentioned Witherspoon but Witherspoon had a unique style and was able to parry Holmes's jab with his cross arm like defence. Witherspoon also has a better defence than Bowe who's defence could be very leaky which was a big fault of his. Bowe liked to mix it up on the inside Holmes wouldn't oblige, and would pepper Bowe with the jab and outbox him from range.
Prime for prime I would comfortably pick Larry Holmes to take a decision. Granted he would have some shaky moments but I think he could win a 15 rounder by about 10 rounds to 5 or at worst 9 rounds to 6
I remember when I first saw that fight I heard an announcer talk about how Tim's idol was Ken Norton and I thought "uh-oh".
One of Bowe's biggest strengths was how damn good he was up close. Tying him up doesn't seem like a good plan. Holmes did have a nice uppercut though, and showed in his second career that he was quite good up close actually. No idea how this would turn out. I could see it going either way. I give a lot of credit to Bowe for what Holyfield said about his power -- he said that Bowe's ability to consistently hurt him was better than anyone else he faced, including Foreman. When the durable guys say "yeah, that MF hit hard", I listen.
definitely Larry Holmes. Bowe had problems with outfighters with a good jab and no one had a better jab than Holmes. I know it doesn't work like that, but look at Bowe's fights with Tubbs and Golota. Of course it wasn't prime Riddick but Golota and Tubbs weren't prime Holmes. In my opinion, Holmes UD, much more than Holy in 1993