Flanagan was currently a TV analyst for the Orioles. During his playing career, which lasted from 1975 to 1992, Flanagan had two stints with the Orioles. He also spent part his career with the Blue Jays. Over his 18 years in the big leagues, Flanagan compiled a 167-143 record with a 3.90 ERA and 1491 strikeouts. He was an All-Star in 1978 and won the AL Cy Young in 1979 with a 23-9 record, 3.08 ERA and a 1.186 WHIP. After retirement, Flanagan was the Orioles pitching coach in 1995 and 1998 and he served as the executive vice president of baseball operations for the team from 2006 through 2008.