Decided on his career path after hearing his father Skip's call of a Bob Watson home run off Steve Howe in a 1983 Braves game. Skip had hoped Chip would become a lawyer. Developed his play-by-play experience in stints with the NBA's Orlando Magic and with Sunshine Network's coverage of Florida and Florida State football and basketball. Worked a TBS lead-in to a May 1991 Braves-Cubs game with both his father and his Hall-of-Fame grandfather, Harry. Spent three seasons in the Seattle Mariners' broadcast booth (1993-95) before becoming a part of Fox's first five years of national baseball coverage. Replaced his legendary grandfather in the Chicago Cubs' booth in 1998. Chip had been hired to work alongside Harry, but the elder Caray passed away in February. Left the Cubs after the 2004 season to work with his father, Skip, on Atlanta Braves games.