There's every chance he'd have been in most top 5's at this point particularly given he probably would have faced him against post jail, like he did, and belted him, like he did. There would have been less acceptance of Tyson's poor condition and preparation as Holyfield would have been wayyyyyyy lower odds than Douglas and it would have been seen more as Holyfield was too good. You'd find Bowe may well have slipped into plenty of top 10 lists as well, to take the puzzle one step further. He defeated Holyfield in a series and the one he lost was somewhat controversial. That would be big currency with Holyfield having defeated Tyson.
I’d still consider him unrankeable & exempt from listing because he is a blatant drug cheat. I’d still have him as the best or at worst number two Cruiser, though.