Philadelphia Phillies History on December 16

  • December 16, 1957 – The Phillies sent outfielder Wally Post to the Cincinnati Redlegs in exchange for pitcher Harvey Haddix, a move that shifted a veteran arm into the Phillies’ pitching mix late in the decade. Haddix later became the long-time pitching coach for the Pittsburgh Pirates.
  • December 16, 1970 – Pitcher Grant Jackson, outfielder/infielder Jim Hutto, and outfielder Sam Parrilla were dealt from the Phillies to Baltimore for outfielder Roger Freed.
  • December 16, 1988 – Philadelphia sent outfielder Milt Thompson to the St. Louis Cardinals and received catcher Steve Lake and outfielder Curt Ford in return.
  • December 16, 2009 – In one of the franchise’s most impactful moves, the Phillies acquired ace pitcher Roy Halladay from the Toronto Blue Jays as part of a four-player deal that sent Travis d’Arnaud, Kyle Drabek, and Michael Taylor to Toronto. Simultaneously, Cliff Lee was traded to the Seattle Mariners and the Phillies received pitchers including J.C. Ramirez and Phillippe Aumont, and outfielder Tyson Gillies.

Phillies Personnel Born on December 16

  • Adolfo Phillips (born 1941) – Outfielder who debuted with the Phillies in 1964 after being signed as an amateur free agent; Phillips played with Philadelphia before moving on to the Cubs, Expos, and Indians, bringing speed and power during a solid MLB career.
  • Oscar Mercado (born 1994) – Colombian-American outfielder who played in one game with the Phillies in 2022 after being claimed off waivers from Cleveland. Mercado played in 20 games with St. Louis in 2023 and returned to the organization for the 2025 season on a minor league contract and played at Lehigh Valley.
  • Tom Gorman (born 1957) – Left-handed pitcher who played parts of seven MLB seasons, including some time in the majors with the Phillies in 1986. He also pitched for Montreal and the New York Mets.
  • Tony Kaufmann (born 1900) – Anthony Charles Kaufmann was a pitcher/outfielder who played in five games with the Phillies in 1927. He spent seven seasons with the Chicago Cubs prior to joining the Phillies and five seasons with St. Louis after Philadelphia.

A DEEPER DIVE… What a day! December 16, 2009

By the winter of 2009, the Phillies were very much in a win-now mindset. They had just come off back-to-back National League pennants with a World Series title in 2008, followed by a repeat trip to the Fall Classic in 2009. The roster was still built around a strong core of position players, but the front office knew the rotation was at a crossroads. Cliff Lee was entering the final year of his contract, Cole Hamels was coming off an uneven season, and the club wanted a true, durable ace to anchor the staff for years, not months. That desire led them directly to Roy Halladay, who had quietly let it be known that he wanted out of Toronto and strongly preferred to pitch in Philadelphia.

The Halladay Deal Comes Together

On December 16, 2009, the Phillies acquired Roy Halladay from the Toronto Blue Jays in a blockbuster trade that immediately reshaped the National League. Philadelphia sent Kyle Drabek, Michael Taylor, and Travis d’Arnaud to Toronto, giving the Blue Jays three high-end prospects the Blue Jays hoped would form the backbone of a rebuild. Halladay was not a rental. The Phillies immediately signed him to a three-year contract extension, ensuring that the ace they had coveted would be around well beyond a single season.

For the Phillies, the appeal was obvious. Halladay was one of the most consistent pitchers in baseball, known for his efficiency, durability, and relentless competitiveness. He regularly worked deep into games, saved the bullpen, and set a tone that resonated throughout a clubhouse. In an era when pitch counts were rising and innings were shrinking, Halladay felt like a throwback in the best possible way.

Toronto, meanwhile, was ready to turn the page. The Blue Jays were not contenders at the time and had little incentive to hold onto an expensive veteran nearing his mid-30s. By moving Halladay, they added premium young talent and gained the flexibility to reshape their roster. Drabek was viewed as a future frontline starter, d’Arnaud as a potential long-term catcher, and Taylor as a big, athletic outfielder with upside.

Why Cliff Lee Was Moved

The Halladay trade was only half of the story. The Phillies knew they could not simply add Halladay without addressing the rest of the rotation puzzle. Cliff Lee, despite his outstanding postseason run in 2009, was approaching free agency and expected to command a massive contract. Ownership was not inclined to carry two top-of-the-market aces long term, especially with other financial commitments on the horizon.

Rather than risk losing Lee for a draft pick, the Phillies chose to trade him while his value was sky-high. On the same day they acquired Halladay, they sent Lee to the Seattle Mariners. In return, the Phillies received Phillippe Aumont, Tyson Gillies, and J.C. Ramirez, a package that emphasized upside and organizational depth rather than immediate star power.

How the Two Trades Were Connected

These were not separate decisions. They were parts of a single, carefully constructed plan. The Phillies essentially used Cliff Lee as a bridge to get younger and cheaper in the long term while upgrading at the very top of the rotation. Halladay replaced Lee as the staff ace, but with the added benefit of being under contract beyond one season. The prospects acquired from Seattle helped replenish a farm system that had been thinned by years of contending and previous trades.

There was also a financial logic at play. Moving Lee cleared salary space and reduced future risk, making it easier to justify both the Halladay acquisition and his extension. It was a classic example of a front office balancing the present with the future while keeping the championship window wide open.

How It Worked Out for the Phillies

From a Phillies perspective, the results were overwhelmingly positive. Halladay delivered exactly what the team envisioned. He won the National League Cy Young Award in 2010, threw a perfect game in the regular season, and added a postseason no-hitter for good measure. His influence went beyond statistics. He set a standard for preparation and professionalism that left a lasting imprint on the organization.

The loss of Lee was softened by the fact that the Phillies still had a formidable rotation and, somewhat incredibly, Lee returned as a free agent a year later. That unexpected reunion turned the somewhat controversial trade into a masterstroke. While the prospects acquired from Seattle never became stars in Philadelphia, they served as useful assets and depth during subsequent seasons.

How It Worked Out for the Other Teams

Toronto received mixed results. Drabek showed flashes but struggled with consistency and injuries. d’Arnaud eventually became an everyday major league catcher, though not with the Blue Jays, as he was later moved in another major trade when he and pitcher Noah Syndergaard were sent to the Mets for R.A. Dickey, Mike Nickeas, and Josh Thole. The return of young players for Toronto did not fully replace Halladay’s value, but it did give Toronto a chance to reset.

Seattle’s side of the equation was brief. Cliff Lee was dominant for the Mariners, but he left after one season, leaving the club without a long-term payoff. Still, his presence added credibility and excitement to a franchise searching for direction.

In the end, December 16, 2009 stands as one of the most important days in Phillies history. The trades were bold, interconnected, and rooted in a clear understanding of the team’s competitive cycle. For the Phillies, they delivered an ace, sustained contention, and a legacy moment that still resonates with fans today.