We considered making this a 1 and 1A situation with Roy Halladay and Dave Stieb, but that just isn't our style, so Halladay missed out as the greatest Blue Jay, despite the Cooperstown plaque and the Cy Young.
A First Round Pick in 1995, Halladay first made the Blue Jays in 1998, but as hard as he threw, his effectiveness wasn't there, and he was bouncing back and forth between the Majors and Minors until 2002. Once Halladay figured it all out, he became one of the best hurlers in Baseball.
"Doc" led the American League in Innings Pitched in '02, going 19-7 and making his first trip to the All-Star Game. Halladay was even better in 2003, leading the AL in Wins (22) against only 7 Losses while also topping the league in Innings (266), SO/BB (6.38). He won the Cy Young, making him the first Blue Jay to win that award.
Halladay had shoulder issues through much of the next two seasons, reducing his mound time, but he was healthy in 2006, reclaiming his spot as an American League elite. From 2006 to 2009, Halladay went 69-33, went to three All-Star Games, won a WHIP Title (2008), and was in the top five in Cy Young voting in all of those seasons, with one of those years (2008) as the runner-up. Halladay was phenomenal, but the team around him wasn't, and he never tasted the postseason in Toronto. He asked to be traded, and he was, with a post-2009 deal sending Halladay to Philadelphia, where he won his second Cy Young.
Halladay died tragically when the plane he piloted crashed in 2017. The Blue Jays retired his number 34 the year after, and in 2019, he was inducted into the Baseball Hall of Fame on his first ballot. Halladay went 148-76 with 1,495 Strikeouts with Toronto and was also named to the Canadian Baseball Hall of Fame, and is part of the Jays Level of Excellence.
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