Pernell Whitaker/Winky Wright

I think Pea did well enough to beat Vasquez largely due to two things:
1. He was strong enough to stand up to Vasquez
2. Vasquez was a fairly limited boxer, which allowed Pernell to avoid a lot of his shots despite being quite slowed himself

The problem with facing Winky won't necessarily be that Winky will be too big for him (though of course this will make it difficult), it will be that Winky will be quick enough to hit Pernell quite a bit, where Vasquez couldn't. With a diminished workrate, I don't see Pea throwing or landing enough to beat Winky. Winky could throw 100 punches per round at 154, Pernell can't. It would be a close fight, but Winky would probably just outwork him and land enough shots to edge it.

 

Wright - he was a big man and fought like it. Pea wasn't legendary at 154 despite getting an impressive win over Vasquez. You can't pot shot or pick Wright apart if you are smaller. You need to be the same size as him i.e. Vargas and Taylor, even then you may still lose.

 

Winky UD

 

And he fought totally different than in his prime. Winky´s size, defence and workrate is just too much.

 

I'd edge to Winky. Pea would give him a real fight, because he was still tough as nails at 154 and still had the handspeed and the skills, but ultimately he would not be able to hurt Winky at all and therefore would not be able to deter him walking forward, applying pressure, and unloading a high volume of punches each round. A competitive, bruising, engaging contest would end 116-112 for Wink.

 

Close, but Winky...

 

Insomnia gets KO'd inside of 3 rounds.

 

I think Whitaker would win this fight by UD. In the ring Whitaker was too quick even for Winky.