After retiring, he became an actor and had roles in two of America's best-known movies about boxers, Academy Award winner On the Waterfront and Requiem for a Heavyweight.

[2] Simon was born to Jewish parents Max and Rose in the Richmond Hill neighborhood in New York City on May 30, 1913, and attended John Adams High School.

[2] His two most notable early career losses against well known adversaries came against Lou Nova in 1936 in a six-round points decision and the six-foot-six Buddy Baer, brother of Max, who knocked him out in three rounds in 1937.

[8][9][2] In a well-attended match against a known opponent, Simon defeated Eddie Blunt in a ten-round points decision at the Meadowbrook Bowl in Newark, New Jersey on May 20, 1940.

In one of his best known victories against a highly rated adversary, he defeated Roscoe Toles on December 6, 1940, in a ten-round unanimous decision before 5000 at Detroit's Olympia Stadium.

[14] In the most valiant effort of his career against his greatest adversary, many ringside experts gave Simon the second, fourth, sixth, tenth, and eleventh rounds.

[1] Though he was down repeatedly in the thirteenth before the referee called the fight, his ability to withstand the blows of Louis and win four rounds placed him as a serious heavyweight contender in his mid-career.

[1] He lost to Louis again in his second and final attempt at the heavyweight title, at the coveted venue of Madison Square Garden on March 27, 1942, in a sixth-round technical knockout.

The match was a benefit for the Army Relief Fund, which helped both boxer's reputations and garnered a larger audience, including many servicemen.

[5] He died on October 24, 1969, at Meadowbrook Hospital in East Meadow, Long Island, leaving a wife, Rita (Siebel), whom he had married in 1942, and two children, Alfred and Kathleen.