He attended Wake Forest University, where he studied psychology. In 1983, he played collegiate summer baseball with the Orleans Cardinals of the Cape Cod Baseball League and was named a league all-star.
He played in the majors from 1987 to 1997 for the Pittsburgh Pirates, Atlanta Braves, Cincinnati Reds, and Florida Marlins. He mostly played as an outfielder.
He formerly served as the hitting coach for the Omaha Storm Chasers. Gregg was named as the hitting coach for the New Orleans Baby Cakes in the Miami Marlins organization for the 2018 and 2019 seasons. He became hitting coach of the Lincoln Saltdogs in January 2021.

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