Evander Holyfield and the 10 Saddest Old Fighters in Boxing History

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Evander Holyfield and the 10 Saddest Old Fighters in Boxing History
Al Bello/Getty Images

Ernest Hemingway warned against anyone becoming close to a boxer. 

After spending close to three years tracking legendary Cuban boxer Guillermo Rigondeaux from Havana to Miami, then Los to Angeles and dipping down to Tijuana when I joined his entourage, a title shot in Dallas then to Dublin, Ireland for his last fight, let me assure you—Hemingway knew what he was talking about.

Inside a boxing ring is where most boxers feel the safest in the world. When they lose the ability to defend themselves inside that squared circle, very often they go on to lose everything outside it. 

Few stories end well in boxing. If you follow a career long enough and your heart stays with the horse you rode in on, the cheque for that meal is on the way, and it's guaranteed to be more than you ever thought. 

It's rare that anything this brutal sport adds to your life it doesn't also take away from it. All the same ingredients that make you fall in love with a boxer and his story threaten to punish you in the end.

But there it is. What's the alternative? 

It's part of the journey we sign on for. We're at risk in boxing in a way we aren't in other sports.

You don't play boxing. And when you find a real connection with a fighter, whatever it is we're all struggling for somehow gets reflected in what our heroes in the ring struggle for.

Their fight becomes yours too. 

For a fight fan, nothing is more gratifying than following a boxer on his rise; all that potential leading him into the imagination like a trail of gasoline responding to a match.

Where was Tyson headed after Spinks? What was Bowe capable of after Holyfield?

Could anyone hope to compete with Roy Jones Jr. from any era when he was in his prime?

Our grandparents might've had Joe Louis or Marciano, our dad had Ali—suddenly we might have someone of our own to brag about.

Then, somewhere along the line, it all changes.

In the Cinderella story that boxing can often be, it's always one punch to midnight for a life that might never be the same... 

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