1977 Jimmy Young vs 1959 Cleveland Big Cat Williams. Who takes this bout and why? Williams broke the nose of Sonny Liston in 1959, but was knocked out. Jimmy outpointed hard punching George Foreman on March 17 1977, even decking George in round 12.
On first glance, I'd say Young given his results against Lyle but Williams was superior to Lyle in many ways that would benefit him against Young, such as being much faster, being a better boxer, better fundamentals, etc. Keeping in mind how well Williams did against Machen, a fighter somewhat similar to Young and one of the best technicians of his era, this is a 50-50 fight imo. However it goes, I'm certain it will be much closer than Lyle-Young.
I also think it's 50-50. Both winners would triumph in close, grueling fights. Okay, but not classic fights.