During the De Leon fight, Holyfield's last at Cruiserweight, he was said to be a potentially old 28 who was in reality closer to 40 at the time. Looking at how his career unfolded, I don't doubt that one bit. And I can think of precious few fighters that stayed around so many years past their best than Evander. When should he of quit? Does his legacy suffer as a result of losing to James Toney, John Ruiz, Larry Donald, and looking horrible against the likes of Vaugn Bean? Also, the Odqueno fight was basically a gift, yes?
There are many points I can think of but no later than the Ruiz fights ... he managed to be competitive with Lennox before then but starting with the Ruiz fights he really dropped another notch ...
It would have been best IMO if he stopped after knocking out Moorer to get his revenge. His only losses would have been to Moorer and Bowe, both of whom he had wins over, I don't think he did really anything but tarnish his legacy after this. However, there is no way Holyfield would have stopped after avenging his worst loss in such a fashion, especially coming off the Tyson wins.
He should have retired after the second Lewis fight. Perhaps after taking one last pay day against sombody like Ramhan.
At the absolute latest, the Byrd fight. The Ruiz fights were low quality but did get Holy his fourth belt, plus Ruiz made everyone look terrible in his following 'reign of terror' so that's not so bad. Holy then looked very sharp against Rahman, quick and hard with his punches (and his head, arf). While he got clearly outboxed by Byrd, he still would've gone out fighting for a belt and at that stage of his career and given the opponent, that was no shame to lose either. Getting pummelled and stopped by Toney was an unnecessary embarrassment though, as was the Donald fiasco. The Oquendo win was questionable but more importantly both guys looked bad anyway, and while he did get to challenge for a title belt vs Ibragimov again it was more due to a name value bolt-from-the-blue than really earning it and another clear loss in a lacklustre effort. The fight against Savarese was a good one, arguably (and sadly) one of the best at heavyweight of the year. But I'd be willing to trade that in to remove the losses to Toney, Donald and Ibragimov and the poor Oquendo fight.
I just wrote the exact same thing on the other Holfyfield thread a moment ago. That was the perfect time to gracefully bow out. He had give Lewis two good runs, performing better in the return bout. I actually lost some (not much) respect for Holyfield after the first Lewis fight. Deep down, he must have known he was beaten that night, the looks on the fighters faces when the draw was announced told the entire story. If Holyfield had said, "Ya know, I'm not a judge, but I didn't feel I put my best effort forth tonight. Lewis was the better man tonight, let's do it again!" I would have been much happier. That said, he definitely should have retired before the Ruiz trilogy. That was just AWFUL to watch! AWFUL! Plus, it was total bull**** that Lewis got stripped, and then Holyfield got a shot at a title he had just lost? Everything Holyfield did post Lewis II was forgettable. That was the time.
After the second fight with Lennox Lewis, Evander should have seriously considered retirement. It's too bad that Lennox and Evander didn't have a third and final fight. I still don't think Lewis did enough clearly to win the second fight with Holyfield. There's no denying the fact that he was robbed in the first fight with Holyfield and the justification to give him the decision in the rematch was more than likely based on that fight. I don't think that wrong should have made Lewis' victory the right decision.
What a question! If he (Holyfield) had the brains, in the boxing sense, of Marciano, Tunney, Monzon and most recently, Lewis, then he would have retired while still champion, on top, after making more money than he could possibly ever exhaust. But no, like so many others, he was intoxicated by the glory of it all, and has suffered humiliating beatings over the years from guys who he would have trounced, or at least beaten in his prime. Without a doubt, he should have retired after the tko loss to Toney.
I think after retaining the WBC title in the first John Ruiz fight would have been a good time to call it quits. These two men hardly needed to fight each other three times, and if they had stopped after the first match, it would have done mankind a great service. Upon winning this match, Holyfield became the divisions first 4 time champion. It would have been a good way to go out on a winning note after the Lewis defeat(s).
The Lewis fights would have been the time, I think. Life was giving him a big hint and Evander refused to take it. If he'd wanted to go out on top of the world, then after beating Tyson and Moorer.
I agree on the latter points. He was considered one the best heavies ever after the tyson win the lewis fights tarnished his legacy as the best of his time