Could go either way of course. Trinidad was an overall better fighter but that Jackson power....DAMN! When I play it over in my mind I see Trinidad dropped first, recover to hurt Jackson badly and just as Jackson is about to be finished off, BANG....lights out. Jackson KO 5
Trinidad is the better fighter of the two and I think he manages to get the job done against Jackson. I wouldn't put money on it though.
Even though Trinidad is better, I've always felt Jackson just might get there first... And he wouldn't let him off the hook if he did.
Although Tito was overall the better/greater fighter, I have always imagined in this one that Jackson would land a huge bomb in round 2, Tito would get up but his legs would be too wobbly and they would stop it.
I think Trinidad stops Jackson ... Jackson is a dangerous underdog obviously but Trinidad is the better fighter