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The Grueling Truth - Where Legends Speak / Latest Boxing News & Rumors Today / Boxing History / The Phenom meets his Idol – Sugar Ray Robinson fights Henry Armstrong

The Phenom meets his Idol – Sugar Ray Robinson fights Henry Armstrong

Publish Date: 08/07/2026
Fact checked by: Mike Goodpaster
Only six years before, Armstrong, born Henry Melody Jackson, was conceivably the greatest fighter on the planet, including Joe Louis.

Walker Smith AKA Sugar Ray Robinson turned professional in 1940.

In those three years, he fought forty times, losing once. He scored 32 knockouts. His foot and hand speed were blistering, plus he packed power. Nobody had ever seen anything like him. He beat former lightweight champion Sammy Angot and former welterweight titleholders Marty Servo and Fritzie Zivic.

His lone loss was to future middleweight champion Jake LaMotta in 1943. Robinson had defeated LaMotta at Madison Square Garden four months before, but LaMotta was primed for some revenge. A LaMotta right to the midsection and left to the chin knocked Robinson out of the ring. Somehow, he beat the count, but LaMotta won the fight.

Instead of taking a year off like some of today’s boxers, Robinson fought LaMotta again 21 days later.

Yes, 21.

Robinson found himself on the canvas in the eighth round but survived and won a decision. The two would fight three more times. All were tough, taxing fights. The last one was in Chicago on Valentine’s Day in 1951.

A clever journalist noted the Chicago connection and called the fight, “The St. Valentine’s Day Massacre” 

Six months after his loss to LaMotta, Robinson was pushed to fight his idol, Henry Armstrong.

Only six years before, Armstrong, born Henry Melody Jackson, was conceivably the greatest fighter on the planet, including Joe Louis.

His record at the time was 59-1-1, with 51 knockouts.

His achievements were spectacular.

Armstrong fought 27 times in 1937, scoring 26 knockouts. He cultivated a style of calculated chaos. A

Attack, attack, attack.

Armstrong won his first title by knocking out featherweight champion Petey Sarron in six rounds. Over the next nine months, Armstrong captured the welterweight and lightweight titles.

He’s the only boxer in history to hold three world championships simultaneously.

But by 1943, the now-former champion, with 157 fights under his belt, was fading. He still had enough left to beat most fighters, but not the top guys. Robinson wrote in his book, Sugar Ray, Armstrong came to him and said he needed money. Robinson reluctantly agreed to fight Armstrong.

The fight went down at the hallowed Madison Square Garden in New York City. Robinson was five and a half inches taller and much fresher.

Robinson said, “That night Henry had nothing in the ring with him except me.”

The Associated Press scored all ten rounds for Robinson. Some at ringside said Robinson carried Armstrong and could have knocked him out. Debatable for sure. Armstrong was stopped on his feet twice in his 14-year career. No matter, Robinson was easily.

Reportedly asked after the fight by a reporter if he could have beaten Robinson when he was prime, Armstrong replied, “Mister, I couldn’t have licked this kid the best day I ever saw.”

Armstrong had a different memory of the bout 27 years later.

“Sugar Ray Robinson was clever. It was a disgusting fight. Ray just wouldn’t fight. He told me he was going to run. I almost knocked him out in the third round. I said, why don’t you come on in and fight?. He said, the hell with you, Hank. I ain’t going to get hit like that no more. He won the fight on points,” added the proud former champion.

The truth? It doesn’t matter. Armstrong retired shortly after the fight but came back five months later.

Robinson fought another twenty-two years later. Today, many acknowledge him as the greatest pound-for-pound fighter in history.

Hammerin Henry Armstrong isn’t far behind.

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