Regarding the losses bit... He wasn't past prime for all of those fights. He wasn't in this ill defined, ever changing, post prime period in 1992 in his 29th pro fight - not by any sane measure of the term. Even if he was being 'past prime' shouldn't be used as some sort of mitigating circumstance or excuse. It just makes it too easy for fan boys to just ignore any results outside of a narrow window when their favourite is no longer green and not yet past prime. It's also remarkable how often a fighter is deemed 'past prime' in the eyes of their fans at the exact same time they start picking up losses.
He was 32 against Bowe, that's past prime in most people's book, he'd slowed from the pre-title Holyfield. He wasn't completely past it but it's a mitigating issue. When you assess a fighter you consider how good they were at their best, not at their worst.
I also think he was a lot hungrier in the Bowe rematch. He was certainly better in a H2H sense in the second fight for sure and is arguably his best performance in the ring.
Fighters age differently. I wouldn't say most heavyweights are past prime at 32 though. Nah when you assess a fighter you should look at the whole picture - them at their best, at their worst and everything in between IMO. The only time to assess them completely on their best performances is when you're looking at H2H and judge how they would be on their best night.
If you look at Holyfield against Douglas, Thomas and Dokes and compare the speed and workrate you can see they drop off allot. In other ways Holyfield improved, got stronger and smarter post Bowe, but he didn't have the same stamina and speed that's for sure.
I think both Holyfield and Lewis were somewhat overrated immediately following their defeats of Mike Tyson. At this point, their reputations are fairly settled, and I expect that they will be remembered among the greater champions.
Bowe beat a prime holy for me but anything from moorer onwards can't really be held against him. Past prime he twice stopped Tyson, stopped moorer, beat Ruiz beat Rahman and took 5 rounds off a prime Lewis. That alone is enough to call him great. When you combine that with everything he achieved in his prime it's ridiculous leaving him out of a top ten. H2H he's amazing as well. Big enough to bully the classic sized heavyweights and small enough to out maneouver the super heavyweights. Prime for prime I pick him over the vast majority of boxers in filmed history.
Bowe and Moorer beat Holyfield, but they were only in his class for a breif window. In terms of longevity and resume, they are almost pygmies next to him.
I think holy and bowe is always a pick em fight. Holy was clearly a faded force in the moored fight, he was really there for the taking that night, should never have lasted twelve.y