Blue Jays: 3 trades the franchise wishes they could have back

Detroit Tigers v Toronto Blue Jays
Detroit Tigers v Toronto Blue Jays / Dave Sandford/GettyImages
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No. 2 Saying goodbye to a franchise icon

For 12 years, Roy Halladay gave the Blue Jays everything they could’ve asked for.

He won 20 games twice. He won the Cy Young Award in 2003 and finished in the top-five four other times. By the end of 2009, he trailed only Dave Stieb in a number of franchise records: wins, ERA, strikeouts, shutouts, and WAR. He was the consummate workhorse, leading the league in complete games five times in a span of seven seasons.

But he had yet to accomplish one thing: pitch in the postseason. The Blue Jays constantly played in the shadow of the Yankees and Red Sox in the AL East. They won between 80 and 87 games seven times during the decade but never seriously contended for a playoff spot.

Halladay, with a year left on his contract, saw his time running out. After the 2009 season, when he won 17 games and finished third in the AL with a 2.79 ERA, he requested a meeting with new General Manager Alex Anthopoulos (who had only been on the job for a few months) and team president Paul Beeston.

“Look, if you guys are rebuilding, my clock is getting short. I don’t know how long I have and I don’t want to go through another rebuilding process. I would love nothing more than to win a World Series championship in Toronto, but I don’t know that I have that time,” Halladay said, as recounted by’s Todd Zolecki in Doc, his 2020 biography of Halladay.

Halladay requested a trade. Anthopoulos connected with Phillies General Manager Ruben Amaro Jr. and, after much back-and-forth bargaining, the two sides agreed on a package: Halladay was sent to Philadelphia in exchange for Kyle Drabek, Travis d’Arnaud, and Michael Taylor.

Halladay further cemented his Hall of Fame status with the Phillies, winning yet another Cy Young Award, pitching a perfect game, and throwing only the second postseason no-hitter in history. The Blue Jays hoped Drabek, the son of 1990 Cy Young winner Doug Drabek, would step out of Halladay’s loft shadow. He never did.

Drabek was the 25th-ranked prospect in the league by Baseball America. He was the top pitcher in the Phillies system and was described as having the best curveball in the organization to go along with a low-90s fastball. He had a 3.19 ERA in 23 starts in the minors in 2009, striking out 8.5 batters per nine innings.

Drabek made his MLB debut in September 2010 and made 14 starts for the Blue Jays in 2011. His ERA ballooned to 6.06 and he was demoted to the minors in June before earning another September callup. In June 2012, while pitching against the Washington Nationals, Drabek felt a pop in his elbow and required Tommy John surgery. He appeared in just five more games with the Blue Jays, finishing his career in Toronto with an 8-15 record and a 5.27 ERA.

The other pieces in the trade never played for the Blue Jays. d’Arnaud was part of the 2013 deal with the Mets for R.A. Dickey and has gone on to have a 10-year career in the Majors, including winning a World Series with the Braves—where he was reunited with Anthopoulos—in 2021. Taylor was traded to the Athletics for Brett Wallace the same day as the Halladay trade; Wallace, in turn, was traded to the Astros for Anthony Gose.

Halladay is forever memorialized with his No. 32 banner hanging from the rafters at the Rogers Centre. He’s the only player to have his number retired by the Blue Jays and was the first player elected to the Hall of Fame who began his career in Toronto (Fred McGriff became the second this year). He gave the Blue Jays everything he had, even if he had to go elsewhere to fulfill his postseason dreams.