Terry Norris V Winky Wright ?

I appreciate the well thought out and rational rebuttal. However, I think any version of Winky beats any version of Oscar. You mention that he beat Trinidad, Ike, and Mosley past their primes. I could make the same argument that Winky was past his prime by the time they fought. FYI, he turned pro in 1990, the same as Tito and earlier than Mosley.
A few more facts for you to consider:

1. Winky’s older than Tito and Shane.
2. When their paths crossed, he had eight (8) more fights than Tito and Shane.
3. He had 319 rounds to Tito’s 214.
4. He had 295 rounds to Shane’s 241.

In a perfect world, Tito and Shane should’ve been fresher and closer to their primes than Winky. The fact that they weren’t is a testament to Winky’s greatness, durability, longevity as a fighter.

Now about Oscar: he was still fighting big names and big fights after Winky twice beat Shane. He surely could’ve fought Winky instead of Mayorga and Steve Forbes. Oscar didn’t want to test Winky, which is why they never fought.