DeMola pitched at Commack High School South in Commack, New York. He was drafted out of high school by the New York Yankees in the seventh round of the 1970 Major League Baseball draft. At the time, he told Newsday he was glad to be taken by the Yankees because "Ever since I was a little kid I wanted to be a Yankee." He ultimately chose to sign with the Yankees instead of playing college baseball at Saint Leo University.
DeMola only reached Single-A in two seasons with the Yankees before being released outright at 19 years old. He later said he thought he was cut because of the 1972 Major League Baseball strike, during which time the Yankees made budget cuts. He spent the following season in an auto body shop back in Commack replacing windshields but "couldn't stop thinking about baseball." He reached out to his former high school coach who arranged a tryout with a Montreal Expos scout and gave him a month to prepare. DeMola impressed in that tryout and received a minor league contract with the Expos. Upon signing with the Expos, he told The Palm Beach Post that he resolved to make the big leagues by the time he was 22 years old. He made his Major League debut in April 1974, three months before his twenty-second birthday.
He played through elbow pain during the 1975 season and, by the time he came back for spring training in 1976, he required surgery. He told the Montreal Gazette the surgeons "took enough calcium out of the elbow to lay down the baselines." The following year, he sprained his foot and ankle on the first day of spring training. In May of that year, he broke a knuckle punching teammate Chip Lang in the head during a fight and required another surgery. According to Lang, DeMola took the blame for the altercation but both players were suspended nonetheless.

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