I'd give James Toney a good shot at winning a tight decision against Holyfield. The Toney that fought Jirov had all the tools.
Holyfield at CW was tough but wasn't the hardened experience warrior at HW. At CW Roy Jones would have been too slick and exp and same with Michael Spinks too awkward and exp. Same with Toney. At HW Holyfield beats on three on points.
Toney would knock him out at cruiser as well. Too much a professional when they were both old, way too much a professional for a green Holyfield.
Not exactly Toney was 35, Holy was 6 years older. That's a HUGE difference in boxing At 35 Toney was beating Jirov and Holy. At 39 Toney struggled badly with faded D-level Danny Betchelder. At 40 Toney was dominated by Fres Oquendo but got a gift. At 35 Holy was beating Tyson. At 41-42 he was schooled by Toney and Larry Donald.
Toney might have had all the tools but then Jirov was no Holyfield at Cruiserweight (and neither was Toney). Toney would have been simply outworked.
How many more fights had Toney had? Besides being a short, fat middle fighting at heavy. The Holyfield that fought at cruiser, with limited experience, would not beat the experienced pro cruiser Toney. No way could he box with him. His only option would be volume against a consummate counterpuncher.
If we talk about CW Holy vs CW Toney (say from Jirov fight), Toney would be the toughest opponent for Evander. The only other opponent at CW, who reminded Toney in terms of slickness, skills and counterpunching abilities, was Qawi, but he was even shorter than Toney and already past his prime when he fought Holyfield.
Nelson was a nightmare to fight like plating saw dust fast and very awkward .lost to HWs when massively outweighed and shorter went the distance in the opponents back yard.Holy beats him but wouldn't be pretty.
At cruiserweight hard for me to pick anyone to beat Holyfield he looked incredible at the weight.. I'd have to look to guys like Marciano, Charles, Walcott who we're cruiserweights before the division had been created and still don't know if any beat Holyfield at cruiser. Some of the modern cruiserweight I will say look quite good and I have to watch more of them along with some of the other past cruiserweight champs to pick a guy to beat Holy at the weight.
I wouldn't pick Toney to beat Evander at cruiser, I think Evander would be to busy and give enough angles to off set Toney's counters. Can never count out James Toney though..