I just watched Bivol jab Canelo silly less than a year ago. I know that was at 175 but Winky truly had one of the greatest pound for pound jabs ever and was defensively as sound as a fighter could get. I could see him beating Canelo and would be comfortable making that bet.
Invalid comparison because OP stated this fight is at 160 lbs. You should be comparing Wright to the Canelo of 160 who did 24 rounds with GGG and beat Jacobs. He was a lot better back then than when he fought Bivol at 175 later on. He was actually moving around the ring, used head movement more, had enough stamina to go all 12 rounds, actually used his jab and wasn't so much about spamming 1-2's. He was also hungry for greatness at this point. IMO this was peak Canelo.
I agree that Canelo was better at 160 than 175 but my point was more about how effective Bivol was with the jab than about the weightclass. Come to think of it, GGG was pretty damn effective with jab against Canelo as well at 160.
I'll go with the house fighter winning a controversial decision. And Winky never had big money behind him or a network pleasing style. So close rounds go to the other guy. Another one of those bouts that create a stench in the sport.
Even if He still had success - Winky was past his prime by the time He moved up to the Middleweight division and his physicality was less of a factor there than at the end of his 154 run. It would be very interesting to watch Winky try to press Canelo behind his high guard with a good jab. Canelo is more of a hooker and relies on power even when He's boxing - so that would be similar to Mosley fights for Winky, just the size of Canelo would make it more difficult. At 160 I'd say Canelo close, at 154 probably Winky.
I’d say Winky comfortably. Canelo really has no jab and isn’t a big volume guy. He tries to do just enough. Winky wouldn’t leave many counter punching opportunities either.