Jimmy Key began his career with Toronto in 1984, where he was used as a Relief Pitcher, recording ten Saves, but the Jays management viewed him as a starter, which is the capacity he served for the rest of his 14 Seasons in Baseball.

The Southpaw was an All-Star in his first year as a Starting Pitcher, winning 14 Games against 6 Losses and helping the Blue Jays make their first postseason.  Key would methodically work his way to the top of the Toronto rotation, winning the ERA Title (2.76) and WHIP Title (1.057) in 1987 while finishing second in Cy Young voting and winning The Sporting News Pitcher of the Year.

Toronto continued to improve, adding starters around Key, and building up a true contender.  Key was an All-Star again in 1991, and in 1992, he was part of a rotation that led the Jays to their first World Series Title.  He left Toronto for the Yankees, where he had two more All-Star, and top-five Cy Young finishes.

With the Blue Jays, Key went 116-81 with 944 Strikeouts and an ERA of 3.42.

Jimmy Key played his entire career in the American League East, dividing between three teams, Toronto, New York, and Baltimore, finding success with all three clubs.

Key’s foray into the Majors first came with the Blue Jays, where he was used in late relief as a rookie.  That year ended his bullpen days, as Toronto promoted him to the starting rotation, and he was an All-Star.  Key would remain an essential figure in the Jays’ staff, winning the ERA Title in 1987 when he was the runner-up for the Cy Young.  Key was again an All-Star in 1991, and the following year, he helped take the Jays to their first World Series win.

Key was not in Toronto in 1993 to defend their title as he joined their rival, New York, as a Free Agent.  The Pitcher went to have the best back-to-back years of his career, earning All-Star nods in pinstripes in both '93 and '94, and finishing fourth and second in Cy Young voting, respectively.  In that runner-up year, he led the AL in Wins (17) and was also sixth in MVP voting. 

In his final two years in baseball (1997 & 1998), he was with Baltimore and was an All-Star in what was his penultimate year.  Key left the game with a 186-117 record.