Dick Tiger would ****ing kill Winky Wright. That's a disastrous fight for Winky. Minding his little mobile bunker will get him badly hurt and he might even get stopped. Awful, awful fight for Winky. Maybe the nearest thing to unwinnable you'll see with two genuinely excellent fighters in the ring, kind of fascinating actually, i've never thought about it before. I'll go for Tiger KO12.
I'm taking Winky. I'm a fan of Dick Tiger for sure but Tiger was at his best with guys that tried to match his aggression and that was not how Winky fought. Trading with Tiger usually ended badly but Winky would use his strong jab to pile up points much like Joey Giardello did before he got old in their 3rd fight. I don't think Tiger is knocking out Winky considering no one ever did and Tiger had a sub 50% ko rate. I also don't see Tiger outpointing Winky.
When you have the Wright Winky, any Dick is a Tiger in the sack. ...I'm not sure if that is something I am allowed to type but...Well, we'll find out.