Blue Jays History: Toronto trades Hall of Famer, signs team icon on same date

There will never be a bad time for anyone related to the Toronto Blue Jays to talk about the late, great Roy Halladay. Arguably the greatest starting pitcher in the club's franchise history, "Doc" put together an outstanding 12-year run north of the border to start his big league career that ultimately landed him in the Hall of Fame.

Things didn't start smoothly for him, but he made his first All-Star Game in 2002, won the AL Cy Young Award the next year and added five more All-Star selections and four top-five Cy Young finishes to that list before he wound up moving to the Phillies.

Blue Jays History: December 16 is a historic day in franchise history

December 16, 2009: Blue Jays trade Roy Halladay to the Phillies

15 years ago to date, the Blue Jays sent Halladay, already a franchise icon at this point, to the Philadelphia Phillies for a package that could not have made this deal any more lopsided. Coming back from the Phillies was catcher Travis d'Arnaud, starter Kyle Drabek and outfielder Michael Taylor.

Of that trio, only Drabek made it to the big leagues with the Blue Jays and he had a 5.27 ERA across 39 appearances before being cut loose.

Halladay, of course, won the NL Cy Young Award in his first season in Philadelphia before finishing second in the voting the year after. Notably, he threw a complete game against the Reds in the 2010 NLDS, a single-game outing that etched his name even further into baseball's record books.

There's no doubt that Halladay is one of the greatest pitchers of his generation. The right-hander overcame so much early-career adversity and wound up sailing into the Hall of Fame once he wrapped up his playing days. Even to this date, it's shocking how badly the Blue Jays got fleeced by the Phillies.

December 16, 2010: Blue Jays re-sign Edwin Encarnacion

In a move that wound up working out just a little bit better than the Halladay trade, Encarnacion had put up some "just okay" showings in 2009 and 2010 for the Blue Jays before being non-tendered. Ultimately, he made his way back to Toronto on this date 14 years ago. The one-year deal he signed that day eventually led to the contract that kept him on the Blue Jays through the 2016 campaign.

Encarnacion, alongside Jose Bautista, was one of the most fearsome sluggers in all of baseball during this second stint on the Blue Jays. From 2011-2016, he made three All-Star Games while hitting 210 home runs with 605 RBI across 861 games played. He's known as one of the best power hitters the Blue Jays have ever had, and the single-year pact he signed ahead of 2011 paved the way for that excellent run in the heart of their lineup.

Other notable Blue Jays moves on December 16

The Halladay trade and Encarnacion signings are easily the two biggest moves made by the Blue Jays on this date. However, they're not the only ones that are notable.

Other transactions made on this date over the years include the following:

• December 16, 2022: Signing Chris Bassitt to three-year deal
• December 16, 2021: Inked Gosuke Katoh, who recently joined the Blue Jays' front office
• December 16, 2009: Acquired Brett Wallace from OAK, who eventually netted Anthony Gose
• December 16, 2004: Signed Scott Downs, who went on to have a solid six-year stint in Toronto.