When should Evander Holyfield have retired?

I would say a perfect time would have been after the 2nd Lewis fight. If not then at least after James Toney.

Holyfield, Toney is one knock out I wish I could unsee.

 

Probably after the Lewis fights. Ruiz trilogy was awful, no really important wins after that, some embarrassing losses. Yes I think he beat Valuev so if he hadn't been robbed he would have been a 5 time hw champ, but in hindsight it would have been better for him to just pack it in once Lewis had established himself as undisputed.

 

Certainly after the Ruiz fight for the vacant WBA title in 2000.

 

I concur completely, go out as the champ.

As the showman PT Barnum quote goes "Always leave them wanting more"

 

Circa 2002-2004 after losing to Byrd, Toney and Donald.

 

I agree. I think the Lewis fights showed whilst not his best self, he still had something left in the tank.

 

Agreed - but no later.

I could have well done without seeing the trilogy that ensued. One of the worst, if not the worst, heavyweight trilogies ever.

 

I love Toney as well but I struggle watching that fight between them. Ruiz trilogy was unnecessary. His last status as a heavyweight championship level fighter was against Lewis but he just couldn't beat him despite great efforts. Would've been a great way to go out bcuz no shame in leaving the game after losses to the best heavyweight at that time.


I do think he beat Valuev but how many embarrassing fights did it take to get there? I'd gladly want him to retire after Lewis w his health n money in tact.

 

For me a perfect time to go out was after Lewis II.

After the Moorer rematch would have been damn fine as well.

He absolutely had to have those two career defining wins over Tyson.

 

I would love to see him still fighting.

I am glad he is still active in the sport at his age. He can retire whenever he feels like it.

Evander is a top 10 ATG and no one holds his late career losses against him.

 

Retired after beating Moorer the 2nd time would of been perfect, i wasn't born during this era. But another poster told me after Holyfield beat Tyson, he was considered a top 3 Heavyweight of all time ? So it seems logical to me getting revenge on Moorer, and then calling it a day would of been the perfect time to retire. Everything after the Lewis fight was a hot mess regarding wins and losses.

 

He only beat Tyson once, the DQ is not a win for Holyfield.

 

Last I checked if one party is DQ'ed in a boxing match, the victory will be given to the 2nd party.

 

Yes, the win will go to the 2nd party, but that's not an actual/proper win.