Larry Merchant once told me that boxers fighting past their prime is as old as prize fighting itself.  I think it’s fair to say that most fighters stay in the game beyond their best years.  However, there are some who get out while they’re still on top.  Below is a list of 10 fighters who quit while they were ahead, followed by 10 who didn’t.  I rank these boxers from 1-10, with 1 being the most extreme example.  The fighters who quit while they were ahead all had something left to give to the sport, but they chose to hang up the gloves.  They didn’t necessarily finish with a win (though most of them did), but they ended their careers with their physical attributes still intact, and with the potential to make more money.  The fighters who didn’t quit while they were ahead were all once very talented boxers, but they were eventually defeated by opponents who would normally not stand a chance against them.  These lists are not meant to offer praise to those who quit while they were ahead, nor do they offer ridicule to those who didn’t.  This is a respectful look at how differently the careers of prize fighters can end.

10. Juan Manuel Marquez (56-7-1, 40 KOs ) – Although injury prone, Marquez never showed any indication of serious decline in the ring.  Coming off of a decision win over Mike Alvarado, he still had a few options at the time of his retirement.

9. Timothy Bradley (33-2-1, 13 KOs ) – There was no shame in losing a decision to Manny Pacquiao in his final fight.  Bradley had a few fights left, but he realized that he no longer had the hunger to compete.

8. George Foreman (76-5, 68 KOs ) – Even though he lost a majority decision to Shannon Briggs in his final fight, the boxing public felt that “Big” George deserved to win.  Having previously defeated Lou Savarese, Foreman was still capable of competing with the new generation of heavyweights at the time of his retirement.

7. Vitali Klitschko (45-2, 41 KOs ) – Considered the better of the two Klitschko brothers, Vitali was regarded as the best heavyweight in the world at the time of his retirement.  Instead of seeing how far he could take his career inside the ring, he turned his attention to politics.

6. Wladimir Klitschko (64-5, 53 KOs ) – Although he came up short, Klitschko’s loss to Anthony Joshua should be regarded as one of the best fights of his career.  The public was clamoring for a rematch, but Klitschko decided to call it a day despite the big payday that awaited him.

5. Carl Froch (33-2, 24 KOs) – Coming off of two stoppage victories over George Groves, Froch had many options and had plenty left in the tank.  Instead of capitalizing on his position, he elected to retire.

4. Lennox Lewis (41-2-1, 32 KOs ) – Having established himself as the best heavyweight of his time, Lewis could have pursued a lucrative rematch with Vitali Klitschko. But with his finances secure and with nothing left to prove, Lewis chose to call it a day.

3. Joe Calzaghe (46-0, 32 KOs ) – Regarded as one of the best super middleweights who ever lived, Calzaghe was one of the key figures who put European boxers in the American spotlight.  At the time of his retirement, he was coming off of back-to-back wins over living legends Bernard Hopkins and Roy Jones, Jr.

2. Andre Ward (32-0, 16 KOs) – Having defeated Sergey Kovalev via eighth round knockout, Ward was coming off of his career-best victory when he decided to hang up the gloves.  He is a former gold medalist and two-division champion who had not lost a fight since he was twelve years old.

1. Floyd Mayweather (50-0, 27 KOs ) – Having previously announced his retirement on two occasions, Mayweather wasn’t exactly pushing his luck when he came back for a big-money fight against MMA star Conor McGregor.  Mayweather won the fight as expected, bringing to a close what was arguably the most successful boxing career ever.

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10. Ricky Hatton (45-3, 32 KOs ) – Once the best junior welterweight in the world, Hatton’s decline happened rather quickly.  There was no shame in losing inside the distance to Floyd Mayweather, Jr. and Manny Pacquiao, but an ill advised comeback against Vyacheslav Senchenko that resulted in a knockout loss ended his career for good.

9. Jose Luis Castillo (66-13-1, 57 KOs) – In the early 2000s, Castillo was considered one of the best fighters in the world, a fact that was punctuated by his first fight with Floyd Mayweather, Jr., where many observers thought he won.  But Castillo hung around for too long, losing to the likes of Alfonso Gomez, Jorge Paez, Jr., and Antwone Smith, eventually getting TKO’d by Ruslan Provodnikov in his final fight.

8. Joel Casamayor (38-6-1, 22 KOs ) – A former gold medalist, Casmayor was part of a talented group of fighters in the 130-pound weight class, which included Acelino Freitas and Diego Corales.  He looked shaky in losing a decision to Robert Guerrero, but a TKO loss to a modest-punching Timothy Bradley marked the end of the line.

7. Shane Mosley (49-10-1, 41 KOs) – Once looked at as the #1 pound-for-pound boxer in the world, Mosley looked faded at various stages of his career.  He finally ran into a wall with an inside the distance loss to Anthony Mundine, and a decision to loss to David Avensyan in his final fight.

6. Arturo Gatti (40-9, 31 KOs ) – Gatti wasn’t an A-level boxer, but he was an excellent fighter who always gave every ounce of what he had.  In his final two fights, he could give no more, as he lost via TKO to Carlos Baldomir and Alfonso Gomez.

5. Evander Holyfield (44-10-2, 29 KOs ) – Although he finished his career on a winning note, Holyfield was once the poster child for boxers who fought past their prime.  The former cruiserweight and heavyweight champion who shined from the late 80s to mid 90s would never have lost to the likes of John Ruiz, Larry Donald, and Sultan Ibragimov.

4. Mike Tyson (50-6, 44 KOs ) – Once referred to as the “baddest man on the planet”, Tyson always produced devastating results, even when he wasn’t fully committed to his boxing career.  But stoppage losses to Danny Williams and Kevin McBride convinced the boxing public, as well as Tyson himself, that it was the end.

3. James Toney (77-10-3, 47 KOs) – Although a career underachiever, Toney was one of the best technicians of the modern era, and was once considered the #1 pound-for-pound boxer in the world.  He had shown signs of slipping for years, eventually losing decisions to Jason Gavern (24-16-4) and Charles Ellis (9-3-1).

2. Bernard Hopkins (55-8-2, 32 KOs) – As Hopkins ’s former trainer Brother Naazim Richardson once said, “He’s done everything in this sport except lose disastrously.”  Having set records for the most defenses of the middleweight titles, and being the oldest man in history to win a world title, Hopkins came back for one more fight at age 51 and was knocked out of the ring by Joe Smith.

1. Roy Jones, Jr. (66-9, 47 KOs ) – From 1993-2003, Jones looked like the best boxer to ever put on the gloves.  But his prime ended overnight when he was knocked out by Antonio Tarver, which was followed by stoppage losses to Glen Johnson, Danny Green, Denis Lebedev, and Enzo Maccarinelli.

Doveed Linder is the author of RINGSIDE: INTERVIEWS WITH 24 FIGHTERS AND BOXING INSIDERS, a collection of in depth interviews with various fighters, trainers, corner men, promoters, and officials, including “Sugar” Ray Leonard, Roy Jones, Jr., Angelo Dundee, Emanuel Steward, Larry Merchant, Bob Arum, Steve Smoger, and Jackie Kallen.  The foreword was written by Boxingtalk publisher Greg Leon.  This book is now available on Amazon.com: https://www.amazon.com/Ringside-Interviews-Fighters-Boxing-Insiders/dp/1476664412

Ringside: Interviews With 24 Fighters and Boxing Insiders ...Amazon.com: Ringside: Interviews With 24 Fighters and Boxing Insiders (9781476664415): Doveed Linder, Foreword by Greg Leon: Books