Ruben Amaro’s five worst moves as Phillies GM

The Philadelphia Phillies announced on Thursday that the contract of Ruben Amaro Jr. would not be renewed in a move long awaited by frustrated fans.

Amaro oversaw the team’s successful run from 2009-2011, but he also made several moves that contributed to the team’s nosedive to the bottom of the standings. Viewed as a GM who held on too tightly to the past, Amaro gave out multiple ill-advised big-money contracts and extensions that hurt the ballclub because he desperately believed the team was one of the best in the NL long after their peak had ended. It wasn’t until this season — after consecutive 73-89 seasons — that Amaro saw fit to endure a rebuild. So poorly regarded as a baseball executive, Amaro became a running joke among baseball fans, and it didn’t help when he showed a lack of understanding of statistics with comments like this.

In light of the Phillies finally parting ways with Amaro, we will revisit the GM’s five worst moves.

5. Jonathan Papelbon signing – Papelbon actually pitched well for the Phillies and more or less earned his money with the team, but few moves delineate Amaro’s blindness when it came to the state of his franchise more than this one.

There are few things more useless in baseball than a good closer on a bad team. What’s the point of having a great lock-down guy if you’re not going to be winning very much? Good closers are luxuries, but Amaro failed to realize this when he signed Papelbon to a four-year, $50 million deal prior to the 2012 season (not including his 2016 vesting option). The Phillies were a .500 team in Papelbon’s first year with the team, and then they plunged into fourth place followed by consecutive last-place finishes. Papelbon recognized how poor of a state the Phillies were in when he said at the deadline in 2013 that they should blow up the team and start fresh. It took Amaro two more years to finally realize that.

4. Ryan Howard extension – Many across baseball cringed when Amaro handed out a five-year, $125 million contract extension to Howard in April of 2010 when the first baseman still had two years left on his deal. Howard was 30 years old at that point, and rather than keeping him for the remainder of his deal and letting him go when he and the team would be hitting the decline — and at a point when Howard would be best suited for a DH role — Amaro locked him up. Though most could see that paying an overweight first baseman was a bad idea, Amaro didn’t. Howard’s production swiftly fell off, and he was derailed by injuries in 2012 and 2013.

Now the Phillies are so desperate to get rid of an aging hitter with declining power and no defensive value that they’re willing to pay millions for someone to take on his contract. It got so bad that Amaro even said the team would be better off without Howard. While Amaro is trashing his own deal, fans and critics are repeating the same line they said in 2010 when the deal was consummated: “told ya so.”

3. Waiting too long to acquire Roy Halladay in a trade – One of the hallmarks of Amaro’s tenure as GM was his poor timing, which frequently consisted of him making moves when it was too late. Prying Halladay away from the Blue Jays when he was the best pitcher in baseball was a good thing, but it could have been much better.

As outlined in this article I wrote in 2009, Amaro failed to seize a great opportunity to win a World Series in 2009 — the year he got Cliff Lee — because he refused to part with Kyle Drabek. Halladay finished out the season with the 4th-place Jays, while the Phillies came up short in the World Series. Having Halladay plus Lee pitching against the Yankees might have been enough to turn the tables, but Amaro wouldn’t pull the trigger for the Cy Younger during the season. Making matters even sillier was that Amaro decided to go for it AFTER the season and parted ways with Kyle Drabek, Michael Taylor and Travis d’Arnaud to get Doc. Though d’Arnaud is now looking good for the Mets, you have to laugh at the notion that Drabek — who has done nothing — is what kept Amaro from making this move initially. Halladay, meanwhile, won a Cy Young for the Phillies in 2010 (and pitched a no-hitter in the playoffs) and was an All-Star in 2011. Would have been nice to also have him in 2009, ay Rube?

2. Hunter Pence trade – Before becoming a cult hero in San Francisco, Pence was briefly a Phillie. The Phillies acquired Pence from the Astros prior to the 2011 trade deadline for Jarred Cosart, Jon Singleton and Josh Zeid — a significant haul. The move paid off as Pence was an All-Star that season and hit .324/.394/.560 with 11 home runs and 12 doubles in just 54 games for the Phillies, who lost in the NLDS to the eventual World Series champion Cardinals. But after dealing three prospects for Pence, Amaro turned around and traded the outfielder to another NL contender, the Giants, at the next trade deadline. He got back three players who didn’t do jack for the team: Seth Rosin, Nate Schierholtz, and Tommy Joseph. Meanwhile, Pence played up to his usual standards and helped the Giants win two World Series, including in 2014 where he hit .444 over the seven-game series.

1. Cliff Lee trade – Amaro traded Cliff Lee in the 2009 offseason, months after acquiring him at the trade deadline, only to sign him to a huge free agent contract prior to the 2011 season. Lee pitched well for the Phillies, going 7-4 with a 3.39 ERA after being acquired in 2009. He turned it up in the playoffs, going 4-0 with a 1.56 ERA in the postseason. He was the winning pitcher in their only two wins against the Yankees in the World Series, yet Amaro traded him after that. Instead of having Lee, Roy Halladay and Cole Hamels in the rotation for 2010 when the team’s offense was a force, they were one ace short and lost in the NLCS to the Giants. Showing just how incompetent Amaro was, he then went and signed Lee to a five-year, $120 million contract after the 2010 season. If you were just going to sign him back, why trade him and cost your team a good shot at another World Series? Classic bumbling Amaro.