The Detroit Tigers selected Pittaro in the sixth round, with the 152nd overall selection, of the 1982 Major League Baseball draft as a shortstop. Pittaro played his first professional season with the Macon Peaches of the Class-A South Atlantic League in 1982. Pittaro moved to second base when he played for the Lakeland Tigers of the Class-A Florida State League in 1983. He was promoted to the Birmingham Barons of the Class-AA Southern League in 1984, where he had a .284 batting average and 11 home runs.

Pittaro was invited to spring training with the Tigers in 1985. Manager Sparky Anderson called Pittaro "the best rookie [he'd] seen in 15 years." Due to a strong performance from Pittaro, Anderson considered moving All-Star second baseman Lou Whitaker to third base so that Pittaro could play second for the Tigers, though the Tigers kept Whitaker at second and moved Pittaro to third when Whitaker said he wanted to remain at second. Though he expected to begin the season with the Nashville Sounds of the Class-AAA American Association, Pittaro made the Tigers out of spring training, serving in a platoon with Tom Brookens. Pittaro debuted in MLB on April 8, 1985, Opening Day and had three hits in four at-bats.

Pittaro began the 1985 season with a batting average over .300 in April. However, he began to slump in May and continued to struggle offensively with the Tigers. He was demoted to Nashville during the season after he batted .242 with a .299 on-base percentage and .323 slugging percentage.

⚾