27. Mike Flanagan

Mike Flanagan was the quintessential left-handed workhorse of the Baltimore rotation, a pitcher defined by his intelligence, durability, and a knack for finding the win column. Debuting in 1975, Flanagan became a staple of the Orioles' staff for over a decade, accumulating 141 wins—a total that ranks him among the most successful pitchers in the history of the franchise.

While his career was built on steady volume, his 1979 campaign was a masterpiece of "Peak Performance." That year, Flanagan anchored a pitching staff that led Baltimore to the American League Pennant, winning a league-leading 23 games and capturing the American League Cy Young Award. It was a season where he dominated the traditional leaderboards, finishing in the top ten for ERA (3.08) and WHIP (1.21). Though advanced metrics like bWAR often favored his peers, Flanagan possessed the "big-game" gene, proving to be a vital component of the 1983 World Series Championship team.

Flanagan’s tenure in Baltimore lasted until a trade to Toronto in 1987, but he remained an Oriole at heart, eventually returning to the club to finish his playing career and later serving in the front office. His 141 victories and 1,297 strikeouts remain a testament to his longevity and competitive fire.

In 1994, the Orioles honored his immense contribution to the "Oriole Way" by making him the sole inductee into that year's Hall of Fame class. A champion, a Cy Young winner, and a tireless innings-eater, Flanagan remains one of the most beloved figures to ever step onto the Memorial Stadium mound.