Bildilli grew up in Shepardsville in Vigo County, Indiana, and attended Clinton High School. As a young man, he moved to Terre Haute, where he played semiprofessional baseball. In 1937, Terre Haute's Class B Illinois-Indiana-Iowa League team, the Tots, a St. Louis Browns' farm club, signed Bildilli, then 24, to his first pro contract. He appeared in 15 games and posted a 7–7 won–lost record before the Tots folded on July 3. Bildilli then spent the rest of the 1937 minor-league campaign with the Class C Johnstown Johnnies of the Middle Atlantic League.
In late August, he was recalled all the way to St. Louis, getting into four games for the 1937 Browns (with one start), but he struggled, losing his only decision with a 10.13 earned run average.
Bildilli was back in the minor leagues for the bulk of 1938, but it was a banner year for him. He won 18 of 22 decisions for Springfield of the Illinois-Indiana-Iowa League, and was effective in three appearances in the high-level Texas League with San Antonio. He earned another late-season trial with the 1938 Browns, working in five games and recording his first MLB victory, but he remained ineffective, with 7.06 ERA. St. Louis sent him back to San Antonio in 1939, where he helped pitch the Missions into the playoffs by winning 22 games, tied for tops in the Texas League. Back with the Browns for a third consecutive September stint, he posted two complete games in as many starts and lowered his ERA to 3.32 in 19 innings pitched, setting the stage for his 1940 season, Bildilli's only full year in the major leagues.

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