Against Julio Cesar Chavez in 1990. So Whitaker fights Chavez three and a half years earlier than he would, going in against a younger, fresher Chavez at a slightly lower weight. Lets say Whitaker is 24 fights into his career, just like Taylor, instead of the 33 fights Whitaker had under his belt against Chavez in real life. Also, to make it even more realistic, lets say Whitaker has a cut in his mouth as Taylor did. What's the end result?
The result would be the same. Of course, Chavez was slightly past his prime at their encounter but so was Pernell. At lightweight, it would be probably the exact same score : Whitaker UD Chavez 9-3 or 8-4 at best. At 140, Chavez was an outstanding fighter but Sweet Pea was a master.
At that time Chavez wanted Whitaker, but even Lou Duva made the comment that Pernell wasn't ready for Chavez yet. So Chavez fought Taylor instead.
I seriously doubt if it would come to that. Whitaker would never stay in front & trade with Chavez, like Taylor did. It's just not his style. But one thing is certian, Chavez would have put alot more pressure on Pernell.
To make it more interesting, let's pretend Whitaker lost the first 11 rounds and is about to be stopped on a cut. The referee stops the fight. Can Whitaker get the Decision turned around and win?
The cut in the mouth shouldn't be a problem. He won't be taking many flush shots on the kisser to aggrevate the pre-existing damage. What could detract from his performance is if he developed a broken orbital bone and had swelling and watering eyes. That said, Whitaker has soldiered on through things like swollen eyes (DLH, Rivera fights) sprained and broken wrists/hands (Williams, Ramirez, Jones fights), and even a broken jaw (Tito fight), so not even that would take him totally out of his game. One thing that should be noted, in the Whitaker-Chavez talks about fighting at lower weight classes is work rates. Chavez it should be noted threw roughly the same amount of punches against Meldrick Taylor as he did against Pernell Whitaker. Whitaker, on the other hand, had a much better workrate at the lower weights than what he showed at welterweight. He still threw about 750 odd punches against Chavez at welterweight, but had the fight occured at 140, around 1990, you can be rest assured that he would have been throwing in the 900-1000 range. I don't see Chavez, even if he is sharper, outboxing Whitaker, and I don't see him stopping him, so i see Pea winning on points, albeit closer than their welterweight fight. Would probably be something in the vicinity of 7-5, and of course, if i think that, you can also rest assured that CHavez will probably get the nod.
To make it even more interesting, let's say when Whitaker was on the ascendancy in the 6th round, a seagull flies into the arena distracting Sweet Pea who looks up, and as he does his leg gets caught and snapped off by a bear-trap that no-one noticed in the corner of the ring- could he still win then?? "Would he win if he had a cut mouth"- what an utterly ridiculous debate to start.
Whitaker's movement in 1990 would be much for Chavez, much the same as it was when they fought a few years later. UD all the way, if the judges didn't screw him over and give him a draw.