James Edward Key
Jimmy Key was drafted by the Blue Jays in the 1982 MLB June Amateur Draft out of Clemson University. He would rocket through the Jays system, and by 1984 at the age of 23 he was in The Show. He makes this list because he never overlapped as teammates with Halladay. But also because he posted a bWAR of 29.7 and 28.0 fWAR over nine seasons with Toronto (third highest all-time), compiling a 116-81 record with a 3.42 ERA and 3.70 FIP over 1,685.2 innings, with 28 complete games and ten shutouts. He was also a two-time All-Star as a Jay and finished second in the 1987 Cy Young voting after leading the AL with a 2.76 ERA over 36 starts and 261 innings.
Most importantly, he also went 2-0 in the 1992 World Series win over the Braves, tossing 9 innings and only allowing a single earned run. He allowed just one run in 7.2 innings to lead the Blue Jays to a 2-1 win over Atlanta in Game 4 of that series, in what turned out to be his final start in Toronto after he left the Skydome mound to a standing ovation. In fact, including his second World Series title with the Yankees in 1996, he went 3-1 with a 2.66 ERA over 20.1 innings in the Fall Classic. He also possessed an outstanding pick-off move to 1B, check it out: