Blue Jays All-Time Lists

Blue Jays: Worst trades in franchise history

TORONTO, CANADA - APRIL 4: The Toronto Blue Jays logo painted on the field during batting practice before the Toronto Blue Jays home opener prior to the start of their MLB game against the New York Yankees on April 4, 2014 at Rogers Centre in Toronto, Ontario, Canada. (Photo by Tom Szczerbowski/Getty Images)
TORONTO, CANADA - APRIL 4: The Toronto Blue Jays logo painted on the field during batting practice before the Toronto Blue Jays home opener prior to the start of their MLB game against the New York Yankees on April 4, 2014 at Rogers Centre in Toronto, Ontario, Canada. (Photo by Tom Szczerbowski/Getty Images) /
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NEW YORK – JUNE 03: Roy Halladay #32 of the Toronto Blue Jays pitches against the New York Yankees on June 3, 2008 at Yankee Stadium in the Bronx borough of New York City. (Photo by Nick Laham/Getty Images)
NEW YORK – JUNE 03: Roy Halladay #32 of the Toronto Blue Jays pitches against the New York Yankees on June 3, 2008 at Yankee Stadium in the Bronx borough of New York City. (Photo by Nick Laham/Getty Images) /

December 16th, 2009: Blue Jays trade Roy Halladay for Travis d’Arnaud, Kyle Drabek and Michael Taylor

One of the biggest trades in franchise history saw their soon to be Hall of Famer, Roy Halladay, traded to the Philadelphia Phillies.

It was a different situation in that Halladay more or less picked where he would go. The Blue Jays extended him the courtesy of letting them know where he’d like to end up, and it also helped with their trade negotiations when the acquiring team knew he would re-up there after his current deal with the Jays had expired.

At the time it looked like a promising return, but unfortunately, it’s worked out to be anything but. The Blue Jays received Kyle Drabek, Travis d’Arnaud, and Michael Taylor in return, all promising minor leaguers in the Philadelphia system at the time. The Blue Jays more or less immediately flipped Taylor to the A’s for a first baseman named Brett Wallace, who also had decent prospect rankings at the time.

Sticking with the Wallace trade train here, he was eventually swapped in exchange for Anthony Gose, who played a few seasons in Toronto between the big leagues and Triple-A Buffalo. Gose then eventually began the man who was swapped for Devon Travis, who is the only remaining asset from that first major trade that is still in the organization.

Going back to the original haul for Halladay, d’Arnaud was famously used in the trade with the New York Mets that brought back R.A. Dickey. d’Arnaud was one of the most highly rated catching prospects at the time but hasn’t developed into the star that many thought he would be, mostly battling injuries. If the trade had been centred around him then people likely wouldn’t lament the Mets deal so much, but unfortunately, Noah Syndergaard went with him as well, and we all know how that worked out.

Lastly, what looked to be the prize of the return was Kyle Drabek, son of former Pirates’ pitcher Doug Drabek. He had all the tools to be a top of the rotation starter, but unfortunately, a couple of Tommy John surgeries and a hold of other injury problems cut his career short of it’s potential. He did get a few chances in Toronto but ended up finishing with a career as a Blue Jay with an 8-15 record, posting a 5.26 ERA and a 1.698 WHIP in 30 starts and 43 total appearances.

While Dickey’s contribution was underrated while he was in Toronto, and Devon Travis could still salvage his career and return to the .300 hitter potential he flashed a few years ago, you have to consider the return for Roy Halladay to be pretty light. You could consider the trade tree to be a decent one if the Blue Jays had ended up with Travis and Dickey at the end of things, but you have to remember that Syndergaard went too. As bad as the return was for Halladay on its own, that’s what makes it even worse.

Jays Journal Expert: Chris Henderson

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