The Toney who fought Nunn and McCallum against the Wright who outclassed Trinidad. Two fighters known for their great defense. You have the high guard defense and southpaw jab of Wright against the shoulder roll defense and counterpunching skills of Toney. This would have been a highly tactical yet fast paced match up similar to that of Toney vs McCallum / Nunn or Wright vs Vargas / Taylor.
I have to go with JT in this one. Toney excelled against southpaws and with 160 not being Winky's natural weight, I just don't see any advantages for Winky. The Toney that fought McCallum and Nunn does not lose to Winky. With that said, Winky had the talent and skill to win some rounds but I just don't see him getting it done. I don't think Winky's win over Tito was all that impressive compared to his wins over Mosley. Tito had been fairly inactive at that point with a win over natural WW Ricardo Mayorga being his only fight for three years before Winky.
Winky has absolutely NO CHANCE in this matchup. Other than having better discipline to not blow up in between fights, there is literally nothing that Winky does better than James Toney. He also wouldn't have any physical advantages over Toney. Toney could get complacent from time to time, so, Winky probably lasts the distance. But, if Toney came out with a chip on his shoulder (like in the Nunn fight) he likely stops Winky.
Toney is a relatively poor style matchup for Wright, Wright is great against guys who don’t have great upper body movement and lack a variable lead hand, and he’s able to tattoo them with that jab through that poor upper body movement and over their poor lead hand variability (feinting up and down with it, changing the position and speed etc). Toney had great upper body movement and a decently variable lead hand, and since Wright used the earmuff defence, which had its limitation, it would allow Toney to use them great combinations, right the body, uppercuts etc, he had a great punch selection and an earmuff defence is a bad idea against someone with a great punch selection (when they can establish it) Trinidad had a great punch selection, but was limited at range, so that allowed him to be picked off, and he had to get close to do anything, he couldn’t force Wright to shell up from the outside, whereas Toney could, and then light him up at all ranges.
