Name every heavyweight you think would beat a prime Riddick Bowe

The top of the list, strangely enough, is Riddick Bowe.

 

I'd put Dempsey in as a maybe, in a lot of ways Bowe's flaws reflected Dempsey's; they could box beautifully one second, then waltz in and throw haymakers the next. Considering Bowe loved to slug and give up his reach advantage, and how often he got hurt against Hide and Holyfield who weren't much bigger and probably didn't hit harder than Jack. That said, Dempsey's 190 pound frame probably can't take much of what Bowe dishes out.

I would be pretty confident in Vitali beating Bowe, there's a decent gap in durability there and Bowe is there to be hit.