Probably the calzaghe fight, as it was his final shot at a work title.
John Ruiz fight where he became the first middleweight to win a share of the heavyweight championship. He knew that the Ruiz fight was the only fight he could win in the heavyweights and that he had no chance against the other heavyweight champions and top contenders if he were to linger in the division and try to defend his newly won title. He also knew that he had tinkered so much with his body and maximized it for that rare chance to win the heavyweight crown and there's no way to get safely and viably back down to the light heavyweights. He even never entertained going down to the cruisers where Vasili Jirov and James Toney and a bevy of powerful fighters resided. he should have retired after the Ruiz fight for he had boxed himself in a dangerous situation where tinkering with his body and body weight will surely doom him sooner than later.
I think it should have been........Jone's last bout.
Fans might not have liked the losses and the beatings, but Jones beat everyone, got all the various weight class belts, and was obviously not afraid to lose. In the end, the losses may have been the one thing he himself wanted to taste. And, if he wanted to find past his peak, well, that was up to him.
It was like Stephano/Callas. Sure, they were washed up at the end, but opera lovers kept buying tickets, and they kept right on singing.
Jones was fighting for his own reasons, and anyone who knows boxing knows sometimes fighters go too long.....(Ali is the poster-boy for that). They put their health at risk, for sure, and that is a reason to stop them. But otherwise, if they want to box....let them.
Not everyone is as crafty as Marciano.
After the John Ruiz bout or the Antnio Tarver bout. One of those.
After the first Tarver fight. Though he won by majority decision, it was obvious that he's diminished. After that fight, the losses started piling up against fighters he'd have whupped in his prime, e.g. Tarver, Johnson, Calzaghe and a host of unknowns.
After his SECOND fight with Antonio Tarver because after Tarver gave it such a good go the first fight ,Tarver deserved a rematch in what was a controversial decision ,therefore the second fight became even more intriging ,therefore generating higher ratings and more revenue.
Bundini nailed this one, I agree, the fist Tarver fight should have been Roy's last fight.
Past prime series...