Leonard was known for his speed, excellent boxing technique and ability to think fast on his feet. He also was a hard hitter, who scored 69 KOs out of his 157 wins. Leonard was defeated 11 times and was held to a draw on 5 occasions. As was common in the era in which he fought, Leonard engaged in several no-decision matches and is believed to have fought 213 bouts.
Leonard challenged welterweight champion Jack Britton for his title on June 26, 1922. In a suspicious ending, Leonard appeared to be winning the fight when he knocked Britton down in the 13th round. Then, in a totally uncharacteristic and unexpected move, Leonard proceeded to hit Britton while his opponent was down on one knee. The referee promptly disqualified Leonard.
Leonard is widely acknowledged as one of the greatest lightweights who ever lived. In its September 2001 issue, The Ring magazine ranked Leonard number 2 in its list of the greatest lightweights of all time.
He lost most of his considerable fortune in the stock market crash of 1929, and embarked on an ill-advised comeback in 1931. Although described as pudgy and slow, the balding Leonard won 23 fights, albeit against nondescript opposition, before meeting a championship caliber fighter. On October 7, 1932, his career ended when he was TKOed in 6 rounds by future champion Jimmy McLarnin.
Leonard fought with his head. His most famed rival, Lew Tendler, claimed that Leonard had talked him out of the title by whispering disconcerting things between punches. Leonard's version: "He caught me over the eye with a left and I felt my knees going under me. I said, That was a good punch, Lew.' I said it in a friendly, matter-of-fact tone of voice and it put the fight on a different plane. Lew snarled, 'Never mind that stuff, come on and fight.' But I stuck out a restraining hand and said, 'No, Lew. That was really a good punch. It was all right.' Lew paused again, and by that time I had recovered my senses."
Before Leonard's fight with Richie Mitchell, the referee explained the then-new rule that after scoring a knockdown, a boxer must go to a neutral corner. Leonard suddenly registered perplexity. "Let me get,this straight," he said. "As I understand it, every time I knock him down I'm to go to a neutral corner." Mitchell looked nervous. Leonard knocked him out in the sixth round after Mitchell knocked Leonard down in the first round.
After his boxing career was over, Leonard was a front man for National Hockey League owner Bill Dwyer of the New York Americans, who had secretly purchased the Pittsburgh Pirates of that league. Leonard was supposed to appear as if he owned the team. The team suffered both at the gate and on the ice. The team moved to Philadelphia for 1930-31, and then folded.
Later, Leonard became a popular boxing referee. After refereeing the first six bouts of the April 18, 1947, card at the St. Nicholas Arena in New York, Leonard was stricken with a massive heart attack during the first round of the next bout, toppled to the canvas, and died in the ring.
Leonard was inducted into the International Boxing Hall of Fame.
Leonard was also inducted into the World Boxing Hall of Fame.
Leonard, who was Jewish, was inducted into the National Jewish Sports Hall of Fame in 1996.
Leonard was inducted into the International Jewish Sports Hall of Fame in 1979.
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