He later attended Trinity College in Hartford, where he studied economics. He had an academic scholarship to study at the school until he started partying too much in a fraternity. While at Trinity, he studied economics and played for their varsity baseball team, with whom he also threw a no-hitter. He played summers in Canada, in the Halifax and District League, for the Truro Bearcats. While with Truro, he caught the eye of former Chicago Cubs shortstop Lenny Merullo in 1956, who signed him to play for the Cubs that year. Sources differ on the exact amount of the contract, but Drabowsky himself said it was for $75,000 ($ today). This made Drabowsky a bonus baby, meaning the Cubs would have to keep him in the major leagues for two full seasons or expose him to waivers.