Toronto Blue Jays and the Roy Halladay Trade Tree

DUNEDIN, FL - FEBRUARY 22: Pitcher Roy Halladay
DUNEDIN, FL - FEBRUARY 22: Pitcher Roy Halladay /

On December 16, 2009, new Blue Jays GM Alex Anthopoulos traded away the pride and joy of a generation of Blue Jays fan in Roy Halladay.  Halladay was going into the last year of his contract and as he was turning 33 at the start of his next season, his time in Toronto was coming to a close.

With the Blue Jays coming off a season where they were 13 games under .500 it was clear Toronto was not in a position to push for a post-season berth.  So after 15 seasons in the Blue Jays organization, 148 wins, one AL Cy Young and six All-Star Appearances, Roy Halladay was traded to the Philadelphia Phillies.

While injuries eventually derailed his career in Philadelphia, he was very impressive in his time there.  Halladay would throw a no-hitter in his fourth appearance for the Phillies, make five post season starts over his first two seasons, which included a masterful perfect game in his first ever post season appearance. Halladay would also win the NL Cy Young in his first season and finish runner up in his second season.

Injuries derailed his last two seasons and after starting just 13 games in 2013, he signed a one day contract with the Toronto Blue Jays and retired on December 9, 2013.

In return for Halladay, the Blue Jays essentially made a three team trade which saw them get young pitching prospect Kyle Drabek, a 20-year old catcher Travis d’Arnaud who was touted to have high-end hitting abilities and able to manage a game as good as any catching prospect, and a power hitting 23-year old first basemen in Brett Wallace.

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There was a lot of hype coming with Drabek as he was the son of former Cy Young award winner Doug Drabek, was a former first round pick and was excelling through the minor league system.  After dominating in the minor leagues in 2010 with New Hampshire and being a September call-up he broke camp in 2011 with Toronto.  Drabek struggled in his first long stint in the major leagues and was sent down to AAA by mid-season where he continued to struggle with Las Vegas, but was still able to get a late season call-up.

In 2012, he again started the season with Toronto and began the season very well and through April he was 2-2 with a 2.40 ERA, but things started to go down after that.  In a start on June 13 he tore a ligament in his elbow, missed the remainder of the season and was never able to rebound. After the injury, Drabek was able to get into just five games over the next two years in Toronto, and prior to the 2015 season he was placed on waivers. Drabek had stints with the White Sox and Diamondbacks over the following two seasons but pitched in just four major league games.  Over the next few seasons he played in different minor league and independent leagues and has now been out of any baseball since 2018.

Brett Wallace only played half a season in the minors for the Blue Jays before being traded for Anthony Gose, another prospect, but unlike Wallace was not a power hitter and was more known for his speed.  In his first year in the Jays organization, Gose stole 70 bases for New Hampshire, making fans dream about his speed.

Gose would eventually make his way up to Toronto and played in 202 games over three seasons collecting 34 stolen bases on a .234 average, but the Blue Jays decided to make another move, trading Gose after the 2014 season for Devon Travis. To this day, Toronto still won this trade, but if injuries didn’t derail Travis, this trade would have been completely lopsided.  Travis played parts of five seasons with the Blue Jays, playing in 316 games and batting .274 with 35 home runs and 153 RBI. Travis had a lot of potential and was known as a great teammate, but after missing his entire 2019 season the Blue Jays decided to designate him for assignment, which he refused and made him a free agent.

The final piece of the trade, Travis d’Arnaud makes me cringe a little bit.  The Blue Jays had what I thought a future backstop that would control a game. I started hearing rumours that the team was going to trade him and Noah Syndergaard for a 38-year old knuckleballer with three good seasons in his career.  The Blue Jays ended up doing the deal and shipped Travis d’Arnaud a way in a deal for R.A. Dickey.

You can’t really complain with the numbers that Dickey put up as a Blue Jays, as he was durable and was an innings eater, there was just no confidence when he took the mound.  Dickey finished up his four year career with the Blue Jays with a 49-52 record and 4.05 ERA, however, after pitching moderately well in his first playoff performance in 2015, he was pulled after recording just five outs in his second appearance. In the Blue Jays 2016 playoffs, the team decided not to add him to the roster. Dickey went to free agency that off-season, and played out that final year with Atlanta, then retired.

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In the end looking back, the Blue Jays got Kyle Drabek, parts of Anthony Gose and Devon Travis and used Travis d’Arnaud to acquire R.A. Dickey; while the Phillies got a superstar for two and a half good seasons.  It is often said whoever gets the better player often wins the trade, and this deal showed no different in my opinion. The Drabek and Wallace pieces were lost for nothing before any of those prospects ever amounted to much in the major leagues, while d’Arnaud would be used as part of an over payment for a middle of the rotation starter.

What did you think when the trade happened, and what did you think looking back at it now?