Leonard (Tommy) is born in Springfield.

Tommy Leonard grows up in Westfield, joins the U.S. Marine Corps in 1952, and runs his first Boston Marathon in 1953. He goes on to run the race more than 20 times, and, after becoming a bartender at the Eliot Lounge in 1972, makes that spot a gathering place for runners and organizes the now annual 7.1 Falmouth Road Race in 1973. After moving to Houston briefly in the late 1980s, he returns to the Boston area and tends bar at the Brothers 4 in Falmouth. He dies in Falmouth on January 16, 2019, and is buried in the Massachusetts National Cemetery in Bourne.