Victim of his own success?
What works against the case for including Stieb on this ranking is again something completely beyond his control; he pitched on Blue Jays teams that were far more successful as a group, and enjoyed far more regular and postseason success, culminating in a World Series championship in 1992. Which for the purposes of this ranking, makes him a victim of his own success.
The Blue Jays would lose three times in the ALCS from 1985 to 1991, before finally advancing to the 1992 World Series against the Atlanta Braves. That level of success meant Stieb was surrounded by some incredible talent, including some great starting pitchers.
Halladay, by contrast, would pitch on some very average Blue Jays teams in the lean years from 1998 to 2009, which included eight third place finishes, two fourths and a fifth in the AL East. The closest Halladay ever came to the postseason as a Blue Jay was the 2006 team that finished in 2nd place, 10.0 games back of the Yankees. Sadly, his talents were wasted on a team that couldn’t keep up with the top teams in the East.
So for this ranking, Halladay makes the rotation only because Dave Stieb was surrounded by a much better pitching staff.
Before we go on, let me emphasize how important Stieb is to this franchise's colorful history.
What more can we say about Stieb apart from the fact that his continued omission from the Hall of Fame is one of the greatest baseball travesties of our lifetimes? A 5th round draft pick out in the 1978 MLB June amateur draft from Southern Illinois University, Stieb joined the Blue Jays Level of Excellence after a 15 year career with the team.
As a Blue Jay, he went 175-134 with a 3.42 ERA and 3.82 FIP over 2873.0 innings, with a cumulative bWAR of 56.9 and fWAR of 43.6 (fWAR from FanGraphs uses FIP, whereas bWAR from Baseball Reference uses runs allowed per nine innings; MLB averages the two to come up with their WAR number). He led the AL in innings pitched in both 1982 and 1984, and racked up 103 complete games and 30 shutouts for Toronto, including the franchise’s first and only no-hitter on September 2, 1990.
He also earned seven All-Star selections, and led the AL in ERA at 2.48 in 1985, when he helped lead the Blue Jays to 99 wins and AL East pennant with 27 quality starts (six innings pitched with three earned runs or less allowed) and 6.8 bWAR. That marked the first ever postseason appearance for the then-nine-year-old expansion franchise, where they lost to Kansas City 4-3.
In fact, from 1982 to 1985, Stieb had a cumulative bWAR of 28.3 and fWAR of 20.0, averaged 36 starts and 275 innings per season with a 2.91 ERA, and could have had as many as four AL Cy Young awards if the voters had valued WAR and quality starts like they do in today’s game. The quality start stat was only created in 1985.