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Mike Tyson, Donald Trump, and “Blood” — Revisiting the Most Epic Street Fight in U.S. History

Mitch Green had a bone to pick with Tyson, but it was Iron Mike who broke a hand during their Harlem brawl.

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Most Americans probably think the most historic street fight to ever take place on U.S. soil occurred when Rocky Balboa took on Tommy Gun outside a bar in Philly on November 16, 1990, when Rocky V was released.

They’re wrong.

The craziest street fight in American history did involve an ’80s boxing legend brawling outside of the ring, but his name wasn’t Sylvester Stallone – it was Mike Tyson.

On the morning of August 23, 1988, Tyson was on East 125th Street in Harlem with a pair of pals to pick up a leather jacket at an all-night clothing store called Dapper Dan.

NEW YORK – MAY 20,1986: Mike Tyson talks to the press after winning the fight against Mitch Green at Madison Square Garden in New York, New York.Mike Tyson won by a UD 10. (Photo by: The Ring Magazine/Getty Images)

The jacket – which cost $850 and was embroidered with the words ”Don’t Believe the Hype” on the back – was important enough to Tyson that he was picking it up at 5 a.m.

On his way out of the store with the jacket and his buddies, the heavyweight champion of the world bumped into an old acquaintance – Mitch “Blood” Green.

Green – a heavyweight who ended up with a career record of 18-6 and a mouth that spoke as if that mark was much better – and Tyson had fought two years earlier in May of 1986. The 10-round decision unanimously went in Tyson’s favor, but Green did become only the second opponent to last that long with Tyson up until that point, who rose to 21-0 with the lopsided win.

Still angry over the decision, Green approached Tyson and either demanded a rematch, insisted Tyson’s promoter Don King owed him money, or both.

Boxer Mitch Green. August 30, 1988. (Photo by Neil Schneider/New York Post Archives /(c) NYP Holdings, Inc. via Getty Images)

The money would come later but Green got the rematch immediately as he and Tyson began to brawl outside on the street in front of Dapper Dan.

There’s no way of knowing what exactly happened during the fight or who fired the street-fight punch heard ’round the world, but when the dust settled it was pretty clear Tyson had gotten the better of Green, again.

Following the brawl, Green’s left eye was swollen completely shut and he needed five stitches to sew up his face. Though he was the victor, Tyson didn’t escape unscathed and had a fracture of the third metacarpal in his right hand which put his upcoming title defense against Frank Bruno in jeopardy.

(Original Caption) 8/24/1988-New York, New York- Heavyweight Mitch Green sports a puffed eye and a cut on the bridge of his nose as he tells reporters in NYC about his early morning fight with Mike Tyson, Aug. 23rd..

Enter Donald Trump.

Working as Tyson’s advisor at the time, Trump quickly had to negotiate a deal that would allow Tyson to fight Bruno at a later date once his hand had healed.

And quite a deal it was.

Originally scheduled to be fought in October on Bruno’s home turf at Wembley Stadium in London, the bout was shifted to the United States and eventually took place the following year in February at the Las Vegas Hilton.

He might not have needed the home-ring advantage Trump had negotiated for him, but Tyson took care of business on home soil and won on a technical knockout in the fifth round.

(Original Caption) 5/21/1986- New York, NY- Mitch Green’s hair goes flying as undefeated Mike Tyson rocks him with a fistic barage during their 5/20 bout here. Tyson won the fight by unanimous decision, running his record to 21 wins and no losses. Nineteen of his wins were by KO’s.

As for the man who had gone 10 rounds with Tyson in ’86 and lost, he tried to defeat the champ in the courtroom and hit him with a lawsuit seeking $25 million for injuries sustained in their Harlem brawl.

It took years, but the lawsuit was finally settled in 1997 with Green getting an amount that was a little shy of the $25m he was seeking: $45,000.

If that amount seems low, consider the decision was reached using evidence including a deposition from Tyson in which he said: “Mr. Green is a very large man, and I was afraid of him. I hadn’t been in a fight in a long time.”

Sadly for Green, the $45k wasn’t even enough to cover his legal bills and, flat broke, he continued to pester Tyson for a third fight that never happened.

Mr. Dan, the owner of Dapper Dan’s clothing store, stands near the site of a street brawl between Mike Tyson and Mitch Green. Tyson was in the neighborhood to pick up a custom-made leather jacket at Dapper Dan’s Boutique, a specialty clothing store next door to the club.
(Photo By: Gene Kappock/NY Daily News via Getty Images)

“Tyson’s a punk. That boy is scared to death of me,” Green told ESPN in 2005. “It’s a damn shame Tyson’s scared of me like that. We could make a lot of money. Aw, man. Tyson’s a knucklehead.”

Unfortunately, 1988 being an age before we all had phone-sized camcorders in our pockets, the fight wasn’t captured on video.

Here’s Balboa/Gunn circa 1990 instead.