I picked two champions per division. That way you have to be a top two guy in your division to be champion. It's also more meaningful to be a four division champion instead of cherry picking for championships. Fighters like Money May can't keep using the argument he is the greatest of all-time because no one else beat 24 former or current world champions.
Holmes, Foreman, Tyson, and Lewis all seem fine. Buster Douglas is fine too, as is Witherspoon. Holyfield seems... mostly fine. Call it mild CTE. Bowe seems the worst off of that crop of HWs by far. The two still in shape are Tyson and Holyfield. edit: Roy Jones is fine too.
GREAT thread--tough to choose but ultimately I went with eliminating the tweener divisions and going back to the traditional weight classes. I ALWAYS go back to Jackie Gleason's immortal closing lines in the 1962 version of "Requiem for a Heavyweight" regarding the traditional weight classes---this scene is forever etched in my mind when discussing any boxing subject: "You wanna fight. You fool. You damn stupid fool. Don't you understand? Can't you get it into your silly head? There are only eight champions in this business. Everybody else is an also-ran. The good's great, but the bad stinks! Don't you understand? The odds are all you'll wind up a mumbling idiot! A STUTTERING JERK! WHY DON'T YOU GO HOME! GO HOME!"