When should Holyfield have retired?

[safc1990]

I personally feel after he got stopped by Toney, if not sooner.

[KOTF]

Ruiz I, Lewis II

[TheGreatA]

When he lost to Lewis and began struggling with the likes of John Ruiz.

[PbP Bacon]

After Ruiz I

Holy was 37-38 by then and showing his age. Time to go home and be a family man

[mr. magoo]

I agree with everyone who says that the first Ruiz fight would have been a good time to retire. He was 37 years of age, and had just sealed the claim to being the division's only 4 or 5 time titlist. His record was also a respectable 36-4-1 or somewhere thereabouts. No way did he need to go through a 3 fight trilogy with Ruiz, which frankly was probably even more painful for the fans than it was for the two of them. And needless to say, there was nothing to gain from him fighting Larry Donald, Chris Byrd, James Toney, etc......

Incidentally, retiring after the Tyson fights wouldn't have been a bad choice either.

[janitor]

The Ramhan win looks prety on boxrec.

[mr. magoo]

The Ramhan win looks prety on boxrec.

Agreed, especially considering that he basically beat the same version of Rahman who defeated both Lennox Lewis and Corrie Sanders not long prior, as well as drew in a controversial match against David Tua imediately following. A decent win for an aging ex-champion.

[Dempsey1238]

Than the robbery vs Vauev, In this era, 50 plus year old Holyfiled has a shot to being a 5 time heavyweight champ.

Hell I pretty sure George Foreman is looking at this and thinking of returning to the fray.

[lefthook31]

After the Lewis fights.

[Xplosive]

After the Lewis rematch.

[Rumsfeld]

Ruiz I, Lewis II

Yep! He should have retired after the Lewis rematch, IMO.

And after his lackluster performance with Ruiz, he definitely should have called it quits.

The fact remains, because of his connections, Holyfield got four undeserved title shots. The first bout with Ruiz should never have been for a title. He also was not really deserving of bouts with Byrd, Ibragimov, or Valuev.

I like Holyfield, and do not believe the post-Lewis portion of his career will damage his legacy, but he is certainly not helping his cause by sticking around this long.

He was once a tremendous fighter, but those days are long gone.

[Rumsfeld]

Incidentally, retiring after the Tyson fights wouldn't have been a bad choice either.

Nah, that would have been too early. I respect the fact that he would eventually get revenge against Moorer and go on to attempt to reunify with Lewis.

The Vaughn Bean fight was the one where he started noticeably slowing down, IMO.

[SteveO]

Some people were saying he should have after Bowe knocked him out.

[Rumsfeld]

Some people were saying he should have after Bowe knocked him out.

Who would have thought that one year after that fight, Bowe would twice get battered by Golota and Holyfield would go on to beat Tyson.

This is what's great about boxing.

[SteveO]

Who would have thought that one year after that fight, Bowe would twice get battered by Golota and Holyfield would go on to beat Tyson.

This is what's great about boxing.

Hell yes it is.

It's a great sport with peaks and valleys and surprises like none other.

[My2Sense]

In reality, he should've retired after the third Bowe fight, but because he didn't he was able to finally settle his long-running rivalries with Tyson and Moorer. Still, he was pretty well shopworn by this time.