Wright pounds out a wide decision behind his jab. I'd say the first 6 rounds might actually be quite close because Oscar is a lot quicker. But the last 6 rounds will belong to Wright. Oscar is a better fighter but Winky is a natural LMW.
Wlad would do better than all his common opponents with Pacquaio, doesn't mean he's a better fighter.
Winky peaked after Oscar did. If Oscar jumped up around the time of the Trinidad fight or right after, he'd likely beat Winky close (Why not? He lost to Vazquez, Vargas, and Simon back then). If it took place three or four years later, Winky would have a clear edge.