Roy Halladay’s first big league start went according to script. Although he fell just short of completing a no-hitter, the Blue Jays felt they had a future ace to stick at the top of their rotation for years to come. To an extent, they were right. With that being said, Halladay’s first stint in the big leagues as a whole did not kick off on the right foot.
Halladay, to the surprise of many, struggled on the mound and was optioned all the way back down to Single-A. He was sent there to finetune his mechanics in hopes to reinvent himself. It was a humbling experience for the future Hall of Famer, but one that proved to do him well in the long run. The “Doc”, for the better part of a decade, was a frontline starter in the American League, and one of the best in all of baseball. However, the Blue Jays could never find a way to make the postseason in the tough AL East.

Prior to the 2009 trade deadline, then Phillies General Manager Ruben Amaro Jr. looked to improve his rotation by adding an ace. Despite Halladay being his preference or arm of choice, Amaro settled for Cliff Lee due to a lower asking price from Cleveland. Later that offseason, Amaro got the guy he wanted by acquiring Halladay. He then shipped Lee to Seattle in a trade that has been highly criticized.
Halladay would make his Phillies debut on Opening Day next season in Washington DC. The Phillies would go on to win that game and plenty of others in what proved to be a CY Young Award-winning season. With that, the “Doc” now had a CY Young award in both leagues. To say he was surgical would be an understatement.
His best start of the 2010 campaign may have come on a muggy May night in Miami. Halladay was squaring off against a Florida Marlins team that had failed to make the playoffs in 6 consecutive seasons. He did not disappoint. 27 up – 27 down. Perfection.
His most meaningful start came in Game 1 of the NLDS at home vs Cincinnati. The Reds lineup was loaded, including the likes of Joey Votto, Brandon Phillips, current Phillie’ Jay Bruce, and supervillain Scott Rolen. Halladay, a playoff virgin at the time, did not let the pressure get to him. The result? Just the 2nd no-hitter in postseason history. The first since Don Larson’s Perfecto in the World Series with the Yankees.

Unfortunately, the Phillies were unable to seal the deal and fell short of a world series birth. They were defeated by the eventual world champion Giants in the NLCS. A season later, Cliff Lee rejoined the rotation and paired with Halladay to form a 1-2 punch for the ages. Along with Roy Oswalt and Cole Hamels, the quartet was known as the 4 aces. The hype around the pitching staff was real.
Once again, the men in uniform failed to get the job done when it mattered most, this time falling to the Cardinals in the NLDS. Halladay got the ball in a decisive Game 5, allowing just one run. However, his former teammate north of the border Chris Carpenter held the Phillies scoreless in a complete-game shutout. They have not made the playoffs since.
Despite a drop-off in 2012 and 2013, Doc’s 4 seasons in Philly were extremely impactful, so much so that his wife Brandy decided he entered Cooperstown with no logo on his cap out of respect for both cities Roy played in. Halladay left a lasting impression both on and off the field, and his tenure in the organization will never be forgotten. The only thing that may have made it better would be a world series ring to go along with all the accolades.