High guard southpaw jabber against the African beast. Fighters with movement normally gave Tiger issues but Wright wasn't known for movement but still had that impenetrable high hard and piston jab. Does Tiger have the strength and offense to get through Winky's defense and jab to punish him on the inside? Or does Winky have the style to have his way with Tiger to win via lopsided decision?
Looking at each of their best wins: Tiger - Giardello, Fullmer, Torres, Benvenutti Wright - Mosley, Trinidad, McKart, Qaurtey Seems Tiger was beating the naturally larger MW/LHW opponents while Winky's best wins were more blown up welters and Jr. MW. I probably go with Tiger here. Side note--Winky defeated a "Young Dick Tiger" earlier in his career. No relation that I know of.
You are not taking the same day weigh in rules that the 60's guys fought under. Tito Trinidad was a huge welterweight that walked around above lightheavy. I know Winky himself walked around at 190 pounds. Modern 154 pound fighter's would be lucky to make 160 under the same day weigh in rules. Most fight in the upper 160's or 170's on fight night. I lean towards Winky in this one but I wouldn't count out Tiger. He was a great champion in an underrated era.