Throwback Thursday: Blue Jays trade Roy Halladay to Phillies

One of the biggest trades in Toronto Blue Jays history involved the Philadelphia Phillies.

On December 19, 2009, the Jays traded Roy Halladay to the Phillies in exchange for Kyle Drabek, Michael Taylor, and Travis d’Arnaud.

In this edition of Throwback Thursday, we’ll look at how that trade panned out for either team, as well as Hallday’s career as a Blue Jay. If you missed last week’s Throwback Thursday, we looked at the two trades with the Athletics that brought Josh Donaldson and Matt Chapman to the Jays.

Roy Halladay’s Blue Jays career

The Blue Jays selected Halladay 17th overall in 1995 out of Arvada West High School, making his big league debut towards the end of the 1998 season. In just his second start, Halladay famously threw a near no-hitter, needing just one more out before Bobby Higginson hit a solo home run. It would’ve been the second Blue Jays’ no-hitter in franchise history, something they’re still chasing.

Halladay had a solid rookie season in 1999, but struggled mightily in 2000 as he posted a 10.64 ERA and 6.47 FIP in 67.2 innings pitched. Halladay spent a portion of that season in Triple-A and had to work his way back up to the big leagues in 2001.

When he did, Halladay posted a 3.16 ERA and a 2.34 FIP in 105.1 innings pitched, making 16 starts in 17 appearances. Thanks to a 2.93 ERA and a 2.97 FIP in 239.1 innings pitched, Halladay earned his first All-Star appearance in 2002. The next season, he finished with a 3.25 ERA and a 3.23 FIP in 266 innings pitched for a 7 fWAR, winning the American League Cy Young award.

Halladay was the undisputed ace for the Blue Jays and one of the best pitchers in the league by the time the 2004 season rolled around. The Colorado-native had a tough season that year (by his standards), finishing with a 4.20 ERA and a 3.79 FIP in 133. But he returned to form in 2005, as Halladay posted a then-career best 2.41 ERA and 3.03 FIP in 141.2 innings pitched for his third All-Star nomination.

In 2006, Halladay finished with a 3.19 ERA and a 3.60 FIP in 220 innings pitched, finishing third in Cy Young voting and heading to his fourth All-Star game. While Halladay didn’t attend the 2007 All-Star game thanks to a 3.71 ERA and 3.55 FIP, he finished fifth in Cy Young voting.

The righty’s penultimate season as a Blue Jay came in 2008, where he had a 2.78 ERA and a 3.03 FIP in 246 innings pitched. He had a similar 2009 season, his last with the Jays, posting a 2.79 ERA and a 3.06 FIP in 239 innings pitched.

How the prospects panned out from the trade

In the 2009-10 off-season, the Blue Jays traded their franchise pitcher to the Phillies in exchange for Travis d’Arnaud, Michael Taylor, and Kyle Drabek. In hindsight, this wasn’t a great trade.

Taylor never played for the Blue Jays, as he was traded to the Houston Astros for Anthony Gose. That trade tree extends a little bit further, as the Jays sent Gose to the Detroit Tigers for Devon Travis before the 2015 season, with Travis playing four seasons with the Jays.

Drabek spent parts of five seasons with the Blue Jays, posting a 5.27 ERA and a 5.41 FIP in 172.1 innings. He was eventually designated for assignment in 2015 and claimed by the Chicago White Sox, finishing his big league career in 2016 and his career in 2018.

As for d’Arnaud, the catcher never played for the Blue Jays as he was included in a package to land reigning National League Cy Young winner R.A. Dickey, alongside Noah Syndergaard, on December 17, 2012.

The rest of Halladay’s career

I’d be remiss not to mention the rest of Halladay’s career with the Phillies.

Halladay’s 2010 season was the best of his career. On May 29, 2010, he threw the 20th perfect game in Major League Baseball history, striking out 11 in the process. Later that year, on October 6, he threw a no-hitter in his first postseason game, only the second no-hitter in postseason history. He finished the 2010 season with a 2.44 ERA and a 3.01 FIP in 250.2 innings, winning the National League Cy Young. In the postseason, Halladay had a 2.45 ERA and a 2.85 FIP, winning the World Series with the Phillies.

His 2011 was excellent as well, finishing the season with a career-best 2.35 ERA and 2.20 FIP in 233.2 innings pitched for an 8.7 fWAR, the best of his career. The Phillies were unable to repeat as they fell in five games to the eventual World Series winners, the St. Louis Cardinals.

Halladay pitched the next two seasons with okay results. Shortly after the season ended, Halladay signed a one-day deal with the Blue Jays to retire with the team that drafted him. Tragically, Halladay passed away on November 7, 2017, in a single-passanger plane accident in the Gulf of Mexico.

On the Opening Day of the 2018 season, the Blue Jays retired his number 32, and the Phillies planned to retire his number 34 on the 10th anniversary of his perfect game. Sadly, the pandemic pushed that back until August 8, 2021. In 2019, he Halladay inducted into the Hall of Fame, and later that year, the Jays drafted his son Braden in the 32nd round of the 2019 draft. A touching tribute to one of the greatest Blue Jays in the franchise’s history.