Deadline day then went from bad to worse when Cliff Lee (seen as a prime trade candidate) left that night's start with a reinjured elbow, never to return this year.
There are many reasons the Phillies have spiraled from perennial contender to hopeless doormat -- too many to cover in depth here. But I'll zoom in on one particular, seemingly innocuous tenet of the Amaro administration: his penchant for giving long-term contracts to pitchers like Lee.
It's been almost five years since Amaro inked his first pitcher to a long-term deal. We now have enough hindsight to examine the fallout from what we later learned marked a shift in organizational philosophy.
Before becoming GM, Amaro had Hall of Fame predecessor Pat Gillick to show him the ropes. One of Gillick's strategies was simple: Don't give pitchers contracts for longer than three years.
In November 2005, Gillick's first month on the job, he let Billy Wagner leave town. Wagner wanted a four-year deal, which Gillick wouldn't commit to. His reasoning seemed sound:
"Three years we felt very comfortable with," Gillick said. "Going to a fourth year as the Mets went to, we didn't feel that comfortable. ... I just want to have more flexibility, because you've got to be able to change your roster."
Gillick was vindicated when that flexibility helped the Phillies win a World Series three years later, with Brad Lidge (signed to a three-year extension) saving the clinching game. His World Series rotation included inherited homegrown talent (Cole Hamels and Brett Myers) and two Gillick imports who were either playing on a short deal (Jamie Moyer) or arbitration eligible (Joe Blanton).
So in July 2009, at Amaro's first trade deadline running the team, he stuck to Gillick's maxim and refused to trade for Roy Halladay.
Halladay wanted a three-year extension tacked onto the end of his existing deal. Amaro said:
"I think that any time you get past three years, especially with free-agent pitchers, you put yourself in position where the productivity will drastically change the ability for that player to be productive or healthy."
Instead he traded for Cliff Lee, who was a year and a half from free agency.
By December, with the wound from a World Series loss still fresh, Amaro changed his tune. He shipped out Lee and finally acquired Halladay, giving him a three-year, $60 million extension (amounting to four years of total control).
Amaro broke his rule, but rationalized it:
"As I have always said, I get very uncomfortable with length (of contract) on pitchers," Amaro said. "Frankly, I wouldn't want to go any more than four years. Three years has been kind of our standard on pitching, and I'd like to stay with that standard. That said, when you're talking about a guy like Halladay who has the kind of track record that he has, sometimes special circumstances lead themselves to a different way of thinking. And that's why we were comfortable guaranteeing four, including this year."
Fast-forward to the next offseason. By December 2010, the Phillies had taken a step backward, losing in the NLCS. Amaro attempted to reacquire Lee, but initial talks broke down because Amaro didn't want to break his rule a second time.
According to Philadelphia Magazine, Amaro told Lee and his agent, "You guys are the ones who will have to bite the bullet, because we're probably not going to be able to match the money or contract years of the other guys."
The piece goes on: "At one point, he told them he wasn't going to offer more than five years guaranteed. Really, he didn't want to offer more than three years, a longstanding policy of the Phillies with respect to pitching contracts."
But Amaro relented. He was the toast of Philadelphia when the Phillies swooped in to steal Lee away from the Rangers and Yankees. For five years and $120 million, Amaro got his man. Again.
Fast-forward again, to December 2011. The Phillies had won 102 games, but lost this time in the division series. Once again Amaro's primary offseason target was a pitcher seeking a long-term deal. He signed Jonathan Papelbon for four years and $50 million.
Cue Amaro's rationalization:
"Four years is a little uncomfortable, but on a player like this and a person who has had this pedigree and this background and success, sometimes you go the extra mile to do that," Amaro said. "We felt he was the right guy to take a risk on."
Note that Amaro said Papelbon was the guy, instead of calling him the third guy. Amaro thought he was breaking his rule to go all in. In reality, he was operating without rules. It was becoming clear we were all using the wrong words to describe the Phillies' decisions:
Three increasingly ugly seasons later, we know how things have turned out.
Halladay gave the Phillies two spectacular years, with a Cy Young Award and a runner-up finish, a perfect game, a playoff no-hitter and two division crowns. Then he fell completely apart. His final two years look like a sad typo at the bottom of his baseball card.
Lee gave the Phillies three years nearly as good, including All-Star berths, Cy Young votes and historically dominant stretches. But this year has been an injury-wrecked disaster, and next year is a total unknown.
Papelbon gave the Phillies one All-Star season, followed by a season of diminished results accompanied by a drop in velocity. Despite a rebound this year, his down season sapped his trade value and the open market has since stopped paying relievers as handsomely.
But Amaro knew all along that long-term contracts for pitchers came with concerns like the results above. He said so himself, several times.
He also threw in a six-year contract for Cole Hamels for good measure, though it's too early to debate that one.
"(Six years) is unprecedented for the Phillies," Amaro said, "but we did it with the right person."
But as Amaro has seen, these deals can end poorly no matter how right the person is.
I'm not saying you can't win with expensive pitching, or with long-term contracts for pitchers. I'm not writing about the demerits of taking on long-term risk for a short-term payoff, or even what I'd have done if I was Amaro. I'm saying that while Amaro was seduced by a series of quick fixes, he displayed his lack of restraint for all to see. The issue is not that he gave four pitchers long-term deals. It's that he kept doing it, and kept rationalizing to himself that just this time it's ok.
These deals are not the singular reason the Phillies are a wreck, but they are emblematic of Amaro's many failings. One of the common criticisms levied against Amaro is that he doesn't seem to have a plan. I'd argue it might be more hopeless than that. That even if he did have a plan, there's no guarantee he'd have the discipline to stick to it. Even when he knew the right thing to do, he couldn't help himself. Four times.
So now Amaro seems surprised that his team has crumbled around him. But really he should have seen it coming. He'd been warning everyone all along.