147 - Oscar UD's a drained Winky Wright, maybe even gets a bull**** late stoppage due to star power. 154 - Winky UD's Oscar, he's a H2H Nightmare for any fighter of that generation, the 'big 3' Mosley and Tito were well beaten and Oscar would of been too. Winky is the only name of his era Oscar didn't fight, and with good reason.
Ya, I think 147 Oscar wins but 154 probably winky dink. I just watched him vs. Mosley and watched him toy with him, even giving shane free shots. But I also saw Ferando Vargas beat him and if Vargas can beat him, Oscar sure can at 147. Winky had a great defense but no real power for Oscar to be concerned with. Oscar would pepper him downstairs forcing him to protect his stomach, revealing his ugly mug more.
I have it like this, Oscar on his best day vs Oscar on his worst day. I think at 154 Oscar would be more comfortable than vs Sturm, would be in better shape and would be able to move and throw combos more. Winky would be Winky. It would be the jab jab jab of Winky vs Oscar combos. If this is Vargas era 154 DLH then DLH wins on points.
Oscar is a orthodox leftie with a underdeveloped right hand, which is a problem against southpaws. Similar style would be found in Sturm who won like 8-4 rounds, but at 160. But I also don't think Winky let Oscar pound to the body like Sturm did. Winky 8-4ish at 154 At 147 he would be drained like hell, Oscar goes to the body and gets a star power decision win.
I think Winky would've given Oscar kittens. Winky and Vernon Forrest are two guys Oscar wanted NOTHING to do with and i don't blame him either.
Not two fights I'd really want to see to be honest. I don't think the styles would gel into a fight that was a) exciting and b) one with a very clear winner. I think a lot of the rounds would be hard to split at both weights, that being said I could see myself having a thin Oscar win at 147 where he was much more proven for myself, and Winky with a thin win at 154 where I feel he was more proven. One of those fights where a rematch would probably be in order but not one that people would in anyway want.