The best and worst of Ruben Amaro, Jr.‘s Phillies career

Ruben Amaro, Jr. was handed the keys to a very expensive car. He is going to return an ashtray, two wheels, and whatever antifreeze the cat didn’t drink. It was an impressive head start, taking the keys the day of a World Series parade, with a roster that was expected to contend immediately and indefinitely. The results were unfortunate.

First, let’s note that Amaro is still employed. Nothing has officially changed, at least when it comes to roles and job descriptions. Andy MacPhail is taking over for Pat Gillick as team president, not for Amaro as GM. This is also a good time to note that Gillick is one of only four “team architects” in the Hall of Fame. Gillick is smart, respected, and renowned. He couldn’t fix the Phillies. And the Orioles lost 90 games in every season MacPhail was President of Baseball Operations. If you’re thinking this change is singlehandedly going to fix the Phillies, you’re giving MacPhail too much credit and Gillick not enough.

Still, a change is coming, quite clearly, and the relative excitement for MacPhail is that he isn’t Amaro, hasn’t worked with Amaro, has no ties with Amaro. It would be more surprising for the Phillies to trade Ryan Howard and not include any cash than it would for Amaro to be the Phillies’ GM next year. That’s exciting for Phillies fans, if the Internet is any indication. The anticipation of a new regime is so great, everyone is willing to overlook that the new guy has the word “fail” built into his name with the Phillies’ classic “PH” construction. And they should be. That little tidbit is amusing, nothing more, ha ha, and did you year that Amaro is probably on his way out?

As such, it’s not too early for a postmortem type of look at Amaro’s tenure, and to be fair, we’ll compare and contrast his most inspired move with his least inspired move. This is the good and bad of Ruben Amaro, Jr.

The 2009 Phillies were a fantastic, nearly complete team. Ryan Howard was still hitting dingers. Chase Utley was a perennial MVP candidate, and Jayson Werth helped make the middle of the order one of the best in baseball, if not one of the best in baseball for the entire 2000s. Cole Hamels had hit a rough patch that season, but he was still just 25, the stuff was still there, and his second half was a huge improvement on the disastrous first half. Cliff Lee came over at the deadline and helped the Phillies win their second consecutive pennant. It would have been easy to make a few minor tweaks heading into 2010, nothing more.

Instead, Amaro tore off his shirt and screamed at the heavens, with lightning bolts shooting from his transaction hole. Metaphorically speaking. He didn’t just make a move, he made the biggest move, trading for Roy Halladay, one of the very best pitchers in baseball. There’s a tipping point with a win-now team where it gets a little too easy to pretend that everything is in hand, and this delusion makes GMs hug their prospects even tighter, as if teams are simple farming operations with an easy, predictably cyclical path to sustainability. Amaro said poppycock to that, outbidding the rest of baseball for one of the very best pitchers to ever live.

The three prospects he gave up at the time had incredible value, with all three of them making Baseball America’s top-100 list before the next season, and two of them in the top 30. Five years later, their combined career value is exactly -0.5 WAR. Only Travis d’Arnaud is still a big part of his team’s future, but he didn’t provide a ton of on-field value for his big league teams over the last five seasons. Halladay did, defining the second wave of Phillies dominance. He immediately won the Cy Young and threw one of the most memorable games in franchise history.

Making a move that bold, with prospects that well regarded, to improve a team that was already a pennant-winning machine, is something to celebrate. The dreams of what prospects become -- six years of a below-market ace in Kyle Drabek, six years of a franchise catcher in d’Arnaud, six years of a sure-thing outfielder like Michael Taylor -- are powerful, manipulative things. On the other side of the ledger is just one guy, and he’ll be expensive to keep around.

Amaro did the right thing and realized that the one guy was Roy Freaking Halladay, master of the cutter and slayer of orcs. He emptied the farm for him and didn’t look back. It didn’t result in another pennant, but it probably should have, considering how inspired the move was.

Celebrate that trade. Don’t just make jokes about where the Phillies are now. On December 16, 2009, Ruben Amaro, Jr. made his very best move, an earthquake of a move for a team that needed a nudge. What a brilliant deal.

Later that day, on December 16, 2009, Amaro couldn’t stop screwing around with his phone and everything was ruined.

Clearly, it was the plan to trade Cliff Lee for prospects to replace the ones dealt for Halladay. The thinking, I’ll assume, was something like this:

There might have been considerable ownership pressure to keep just one expensive ace, which shifts the blame from Amaro, slightly. But the Phillies had a chance to have both Roy Halladay and Cliff Lee, two of the preeminent pitchers of their generation, at the same time, with Cole Hamels lurking in the background as one of the best third starters the game had seen since the days of Maddux/Glavine/Smoltz. It was there, right there, a chance that a team like the Phillies absolutely had to take. No one gets to grab all the aces and run like that. Can you even imagine what the Phillies could have been with Lee and Halladay on the same team?

Yes, actually. Because it happened after the 2010 season. The fact that the Phillies spent scores of millions to reacquire Lee makes it seem a little less likely that the initial swap was driven entirely by ownership. There had to be a smidgen of “That makes perfect sense” coming from Amaro, when there should have been a PowerPoint presentation that ended with Amaro banging his shoe on the table to convince the owners that the team needed to have Halladay, Lee, and Hamels at the same time. To not waste the amazing, not-so-young lineup core that had already won them a championship.

The Phillies didn’t win the 2011 World Series with both pitchers, so you might be thinking it isn’t a big deal. They could have lost in 2010, too. But it’s the lack of vision, the lack of urgency with the Lee trade that defines Amaro’s legacy. That was his chance to escape the gravity of the already impressive team he was left with, to build something even brighter, and he got so close with the Halladay deal. So very close.

You might have expected the Ryan Howard contract extension in this spot, an obvious clunker that officially began two years later, with Howard writhing on the ground with a torn Achilles. That extension was ... not good. But what did it cost the Phillies? Money. The money wouldn’t have been delivered to players who would have made a first-place team out of the 2013, 2014, or 2015 Phillies. It was probably going to be frittered away, if not blown completely and utterly. Assume the Phillies did the very best possible moves with all of that Howard money, allocating it exactly where it needed to go. Would that have changed the franchise and prevented the rebuilding years?

Now do a similar hypothetical for the 2010 Phillies with Lee. There’s a lot more confetti involved. There’s an all-time great team, the historic accumulation of talent that people talk about for decades, a 100-win marvel mentioned in the same breath as the ‘98 Yankees or Big Red Machine.

Hyperbole? Perhaps. But the Phillies had a chance to have three of the best pitchers in baseball at the same time, and they screwed it up. By the time they realized it, they had lost a season. They overestimated their own window. They underestimated just how short and fleeting the success cycle can be. The best and worst of Ruben Amaro, Jr. came on one day. Just put down the phone, Ruben. Put down the phone and walk away, and let’s just see what happens.