It's an article of faith: Ruben Amaro's worst move as GM was signing the five year, $125 million deal with Ryan Howard. It was signed at least a year earlier than needed, overpaid by no less than $5 million a year on what he could have hoped for on the open market, and ultimately signed him to a deal that started just after Howard's biggest injury. Not only is all of that true, but Howard's also 33 years old, and started the deal at 32. It will cost the Phillies $10 million to pay Howard to not play for them in 2017 (assuming that's their choice), when Howard will be 37 years old. Yes, Howard has two home run and three RBI titles to go with his MVP, World Series ring, and NLCS MVP, but this was not a very good extension.
I will make some minor defenses of it. Howard hit 14 homers in 292 plate appearances, and had 56 RBI's with just 57 hits in 2012, a year where he put up his worst OPS, so clearly he can still be productive if he doesn't ever reach the heights of his earlier career. If he puts up a couple of 100 RBI/30 homer seasons going forward he can make the contract at least less than a total on-field failure. Also, the Phillies ultimately gave less years and raw dollars than teams did who got first basemen considered by many to be better. Even with that said, there's very little chance that Howard will play up to a level that equates to his contract, so it's not good.
I will argue that it is not the worst move that Ruben Amaro has made though, and no I'm not referring to the Papelbon contract, or even Joe Blanton's absurd post-2009 contract. The truth, on the whole, is that Ruben has not been beaten on many big trades. He did very well in hindsight on the original Cliff Lee trade, got Roy Halladay for a totally reasonable price, essentially stole Roy Oswalt in 2011, and got a solid return on Shane Victorino this past summer before letting him walk (and for that matter by moving the rest of Blanton's contract at all). You can dislike his trade of Cliff Lee to Seattle (I do), but with Lee returning and Aumont's rise to the majors (and the possible rise yet of Gillies), that one's mostly forgiven. Even if you think his trade of Hunter Pence to San Francisco got a light return, Tommy Joseph is one of their top rated position prospects.
The one trade I don't like in hindsight is the original trade to get Pence. It seems that the Phillies bought a version of Pence that didn't quite show up. Yes, he played very well down the stretch in 2011, as a complimentary piece, but with an aging squad beyond that season already on the books, Pence showed in 2012 that he was not the feature piece the Phillies paid for. Pence was a very nice player, but hardly the kind of MVP contender that you build a team's future around. I do understand that he was an All-Star in Houston, but hey, every team has to get one.
Jon Singleton, the "blocked" first baseman we sent to Houston is a top 50 prospect in almost every ranking out there now, and Jarred Cosart is not far behind. Domingo Santana, the "player to be named later" in the trade hit .302 with a .921 OPS in 2012, smashing 23 homers. He is 20 years old.
I know at the time the Pence deal excited people, but the Phillies were cruising to the post-season at the time, and didn't need to replace Dom Brown at that time with Pence. Aside from the damage it did with Brown's confidence, it also did not guarantee anything in the post-season as we saw. If anything, use this as a cautionary trade. There is always going to be a team that makes the big trade in-season, close to the deadline, for a position player who's supposed to deliver the parade that city wanted. You know the trades- Carlos Beltran to San Francisco, Rich Harden to the Cubs, and yes Pence. How many of those trades work out?
Even amongst pitchers the track record isn't good- Schilling to Arizona, Cliff Lee to the Phillies and the Rangers, Harden, Greinke to the Angels, and on and on. Not many of these moves deliver the title. Joe Blanton to the Phillies, Javier Lopez to the Giants, or for that matter Marco Scutaro's trade there- these moves work. Getting the pieces that fit into holes in your team, building deep bullpens and benches, and building depth. A great player can get cold for a week in October anytime, and your season can end if you sell everything to get them. Yes, that can happen to a team too, but it's less likely when you build depth. Bottom line though, I'm hoping the Phillies have learned their lesson from this trade. This off-season's collection of smaller moves suggests that they have.