Many people here might consider this a no-brainer for both as they probably have Leonard rated higher all-time than I do (I think he's in the top 15, but misses out on the top 10) and don't rate Holy as high as I do (I think he's worthy of the top 20). Still, I'm curious if anyone here thinks there's a debate to be had.
Leonard both better and greater by a substantial margin IMO. The more significant wins, with respect to greatness, and in terms of quality just the far more talented and versatile operator of the two. I don't consider Holy to be on Duran/Leonard/Hagler level at all. And no, I don't see the argument for Holy, but if anyone wants to make one, I'll always listen.
Holyfield's longer longevity has to count for something and makes it closer than it would otherwise be. It's always impressive when a fighter takes on multiple generations of top opponents.
Leonard has some of the biggest individual wins in the history of the sport, but I think his lack of longevity and activity over the second half of his career will always be a sticking point when he's compared to other ATGs. Contrast that with Holy, who consistently competed at a top level across three straight decades and was still challenging for titles into his '40s. In general, I think Holy gets underrated in comparison with other ATGs. He was an absolute MONSTER at cruiser - the division equivalent of a Monzon or Hagler IMO. That may not have seemed like much at one time, but the division has had decades to grow and Holy is still an almost universal pick as TBE at the weight. He outfought an accomplished HoFer in only his 12th pro fight and then handed him his only true KO loss in a rematch a year later. Then he spends the next 2 decades frequently competing against fighters who outweigh him anywhere from 10-40 pounds. In the end, I don't think there's a whole lot of fighters throughout history whose career achievements clearly outclass Holy's.
Holy gets underrated P4P IMO, but he has no for being above Leonard IMO. Holy probably comes in my list around the 40 mark, Leonard cannot be anywhere below 20 IMO. Even 20 would be a low rating for him. Better is even clearer IMO, because Leonard probably underachieved with his early retirement. I don't actually see what Holyfield does in a boxing, or athletic sense better than SRL. Bigger heart, sure. Nothing else really sticks out.
