Born in Chicago, Masi attended Austin High School, then began his professional baseball career when he was contracted in 1936 by the Cleveland Indians at the age of 20. In 1937 he played for the Wausau Timberjacks and demonstrated his versatility by playing as a catcher, outfielder, third baseman and as a first baseman. Masi became known as the Pepper Martin of the Northern League because of his head-first slides and prancing running style, while leading the league with 31 home runs and being named to the league\'s All-Star team.\n', '

Masi was then purchased by the Milwaukee Brewers who assigned him to play for the Springfield Indians of the Middle Atlantic League. Baseball Commissioner Kenesaw Mountain Landis found this move to be in violation of baseball rules and allowed him to sign a non-reserve contract with Springfield, meaning that he would be a free agent at the end of the season. He played mostly as a catcher for Springfield in 1938 where his backup that year was the future All-Star catcher for the Cleveland Indians, seventeen-year-old Jim Hegan. Masi posted a .308 batting average with 16 home runs and 97 runs batted in for Springfield, earning a promotion to the major leagues when he was signed by the Boston Braves, then known as the Bees.\n', '

The Bees already had future Hall of Fame member, Al López, as well as future All-Star, Ray Mueller and veteran Johnny Riddle as catchers going into spring training in 1939 however, Masi impressed Bees\' manager Casey Stengel so much that, Mueller and Riddle would be traded before the start of the season, leaving Masi as Lopez\'s backup. He made his major league debut with the Bees on April 23, 1939 at the age of 23. After his father died in 1942, he was given a 3-A draft classification exempting him from military duty as he was the sole support for his family.\n', '

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