Two matchups: Robinson vs Trinidad at 147 Leonard vs Oscar at 147 Who has the better chance of pulling the HIGHLY improbable upset, Felix or Oscar?
Trinidad because Robinson would at least cooperate and fight fire with fire which gives Trinidad a chance to at least get some shots in. Leonard would simply be too smart for anything Oscar would try and I don’t see a scenario where Oscar’s power can threaten Leonard, even if Ray elects to brawl. Neither of them can beat either Sugar, though.
Tito, because of the power, and SRR being a pretty aggressive fighter. His chances are slim since SRR could take a great punch, but I like those chances better than DLH over SRL. DLH did most things at a high level, but SRL did them even better, and one of DLH’s big weakenesses (inconsistent stamina) is one of SRL’s biggest strengths
Robinson vs. Trinidad would likely be considered the more "improbable" upset. Robinson is widely considered the greatest pound-for-pound fighter of all time, and his legacy is built on his ability to dominate opponents across multiple weight classes. He was known for his speed, power, and exceptional footwork, which made him a difficult opponent for anyone. Trinidad, while a great fighter in his own right, did not possess the same level of skill or versatility as Robinson, and would likely have struggled to keep up with him in the ring. In contrast, Leonard vs. Oscar is a matchup between two all-time greats who are considered more evenly matched. Both fighters had exceptional speed and power, and were known for their technical proficiency in the ring.
The difference in class between Robinson and Leonard is smaller than the difference in class between Oscar and Tito IMO. The styles give Trinidad more of a chance, though.
Trinidad has a better chance simply because he has the power to rock and drop SRR. SRR was an offensive and aggressive fighter himself who didn’t mind getting in exchanges but that would present more opportunities for Trinidad’s power. SRL is the kind of fighter to play it safe and not give ODLH any chance to assert himself.
