The Philadelphia Phillies had just lost the World Series to the New York Yankees six weeks earlier. That six-game defeat came after the club had won the Fall Classic the previous season.
General manager Ruben Amaro Jr. was presented with an interesting and exciting opportunity. Longtime ace pitcher Roy Halladay was being made available in trade by the Toronto Blue Jays.
Adding ‘Doc’ to the two-time NL pennant winners could be just what was needed to keep the championship ball rolling.
Amaro was able to negotiate and finalize the deal: Halladay to the Phillies for a trio of highly regarded prospects in Kyle DrabekTravis d’Arnaud, and Michael Taylor.
Halladay was 32 years old at the time. The winner of the 2003 AL Cy Young Award was a six-time American League all-star. He had finished fifth in AL Cy Young race that fall, the fourth consecutive season in the top five of the voting.
Just a year earlier, following that 2008 World Series victory by the Phillies, Halladay had been the runner-up for that AL Cy Young Award. The winner? Cliff Lee of the Cleveland Indians.
Lee was now Phillies property, having been acquired from the Tribe in a trade deadline deal. The lefty was a key addition in helping the Phils nail down a third straight NL East crown, and second consecutive NL pennant.
As word of the Halladay trade broke, there was a brief moment of almost indescribable joy that swept across Phillies Nation. A pitching rotation fronted by Halladay, Lee, and Cole Hamels?
Added to the still dynamic offense that the Phillies had at the time, that trio would certainly elevate the Phillies back to World Series favorites.
And then the other shoe dropped.


Amaro had not formed a Phillies “super rotation” by adding Halladay to his months-earlier acquisition of Lee. Instead, he dealt Lee away at the same time.
Lee to the Seattle Mariners for another three prospects in outfielder Tyson Gillies and pitchers Phillippe Aumont and J.C. Ramirez.
I clearly remember my own mixed feelings at the time. As happy and excited as I was to add Halladay, I was sad and perplexed at dealing away Lee. I simply couldn’t understand how the Phillies GM could allow such an obvious opportunity to dominate to slip right through his fingers.
Lee couldn’t believe it either.
“At first, I didn’t believe it. I thought we were working out an extension with the Phillies,” Lee said at the time“I thought I’d be spending the rest of my career there.”


The story that leaked out from behind closed doors was that Amaro and the Phillies brain trust didn’t believe that they could come to a long-term agreement with Lee.
Halladay would agree to an extension, and would now simply replace Lee, keeping the Phillies at the top. Amaro could then unload Lee for new prospects who would re-stock the farm system.
While it made some sense in a very narrow way, it failed to take into account the reality of the Phillies situation at the time.
The Phillies were playing as an organization at the very top of the game. Their position players were beginning to age through their primes. Now was the time to maximize every championship opportunity.
So how did everything play out?


First, the prospects. None of them has ever amounted to much of any long-term significance for either the Phillies, Blue Jays, or Mariners.
The most interesting case is probably d’Arnaud, who was spun off by Toronto along with a pitching prospect by the name of Noah Syndergaard to the Jays in exchange for R.A. Dickey. He now enters 2017 as the likely Mets starting catcher.
The Phillies would win a fourth straight NL East crown in 2010. However, a big reason they were able to finally overtake and hold off the Atlanta Braves was yet another trade deadline acquisition, this for another ace pitcher in Roy Oswalt.
The Oswalt trade with Houston cost the Phillies a 27-year old lefty starting pitcher just entering his prime in J.A. Happ as well as prospects Jonathan Villar and Anthony Gose.
Halladay went 21-10, leading all of baseball in Wins and Innings Pitched. For his tremendous season he would earn the NL Cy Young Award.
The Phillies would dispatch the Cincinnati Reds in three straight games in the NLDS. Included in that sweep was a playoff no-hitter by Halladay.
However, the Phillies would lose to the San Francisco Giants in six games in the NLCS that year. The pivotal Game Four of that series was a walkoff 6-5 victory by the Giants in a game started by Joe Blanton, who blew a 4-2 lead.


Meanwhile, Lee would find himself in the World Series – against the Giants, pitching for the Texas Rangers. He had gone 8-3 with a 2.34 ERA over 13 starts with Seattle before being dealt to the Rangers.
Lee was pounded in Game One of the 2010 Fall Classic by San Francisco, allowing six earned runs and eight hits over 4.2 innings. He then lost a tough 3-1 decision to a Tim Lincecum gem in Game Five.
It could be argued that had the Phillies kept and signed Lee to a long-term deal, they would have never dealt for Oswalt.
In such a scenario, would Lee have made much of a difference in that NLDS against the Giants? After all, he ended up not faring very well against them in the World Series with Texas.


The Phillies would shock many in the baseball world by then signing Lee as a free agent in the off-season following that 2010 campaign.
Lee was now teamed with Halladay, Oswalt, and Hamels to form the “Four Aces” rotation. Mostly as a result of having these men constantly taking the mound, the 2011 Phillies would win a franchise record 102 games in the regular season.
That 2011 club was likely kept from a World Series crown only by the dominating short-series pitching of Chris Carpenter of the Saint Louis Cardinals.
Would a rotation of Halladay, Lee, Hamels, and Happ have fared as well, in either the regular season or playoffs? Would the Phillies have transitioned in the long-term any better with Villar ready to step in for Jimmy Rollins?
There are so many “what-if” scenarios that branch off from that December 16, 2009 pair of deals involving Halladay coming and Lee going.
The Phillies would have won the NL East in 2010, which they did any way. They also would have been in a position to make the Oswalt deal anyway, pushing them to that 2011 level of dominance earlier. It could have made a difference in the 2010 postseason, with Blanton removed from the rotation.
The dominoes falling one way because of the decision to deal away Lee on that December day in 2009 could have fallen in an entirely different direction had he been retained. We’ll never know for sure.
For Phillies fans who lived through it, that pair of trades remains one of the most controversial elements which we will always consider and debate when looking back on that glorious era in the team’s history.

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