Amaro finds himself in quite a quandary with the July 31 non-waiver Trade Deadline just 12 days away.
If the Phillies trade talents like Cole Hamels and Shane Victorino they will have a hard time making the playoffs for the sixth consecutive season, especially with eight teams ahead of them in the Wild Card standings. But if they keep them and still fall short and then those players sign elsewhere as free agents following the season, the Phillies will have wasted an excellent opportunity to retool for 2013 and beyond by not trading valuable commodities for young talent.
Make the right call and the Phillies continue their winning ways.
Make the wrong call and the Phillies could be hurt not only this season, but beyond.
It sounds like plenty of sleepless nights for the Phillies GM.
"I mean, it's just different," Amaro said. "This is like one of those fun and stressful times of the year, you know? The offseason, right when free agency opens and the July 31 date are the times when you really like your job. Number one, you get to bring in a lot of people in the process. You're talking about your players. You're talking about other players. You're evaluating short term and long term, and you're bringing all of your people together to discuss the plans for the present and the future. To me it's a fun time."
Fun is relative because there are fun times like Amaro's previous three Trade Deadlines, when he acquired Cliff Lee (2009), Roy Oswalt (2010) and Hunter Pence (2011) with the team on the brink of winning a World Series championship, and then there are times like this, when Amaro has to decide whether or not to trade Hamels, if they cannot sign him to a contract extension.
"You try to make the best decisions you can for the short term and the long term," Amaro said. "The job at hand for us is to try to improve. If we continue to improve, whether it's short term or long term, that's what we're trying to do. Every time we talk to another club or we talk internally, our job is to improve. Improve in one area, improve in another area, if we can do that then that's all we can hope."
The Phillies are trying to sign Hamels to an extension, but if they cannot reach an agreement and the team does not show enough improvement before the deadline the Phillies seem likely to trade him.
What is enough improvement in Amaro's mind? What does he need to see?
"There are going to be some determinants with wins and losses obviously," he said. "That will be part of it. But I think every day you continue to assess what's the best thing for our organization, short term and long term. As I've said before, this isn't a team that gets blown up at any time. If we don't feel like we're going to end up being contenders this year, which I still think we are, then we're going to do what we've got to do to be contenders in 2013 and 2014."
The Phillies started 4-2 after the All-Star break. If they continue that pace they would be 10-5 from the break to the deadline.
"It's improvement," Amaro said.
But it doesn't seem like enough, right? The Phillies would be only 47-55.
"It doesn't mean we can't rattle off more wins," Amaro said. "It all really depends on how I feel the team is playing. We're playing a little better baseball now. If we continue to play better baseball that's a good trend. That's a good sign. Hopefully we continue to do that."
Amaro said he will not come to any major decisions in a vacuum. He will be meeting with his top officials in the coming days, folks like David Montgomery, Pat Gillick, Dallas Green, Scott Proefrock, Benny Looper, Charley Kerfeld, Gordon Lakey, Joe Jordan, Mike Ondo and others.
"We have guys that have a lot of different viewpoints, different thoughts," Amaro said. "They've got a lot of different viewpoints and everybody has their own agenda, but my job is to try to do what's best for the organization. Hopefully we take all this information and make the right decision.
"Sometimes you go with your gut. Usually I'm a consensus kind of a guy, but sometimes we're split 50-50. I guess that's why I wear the hat."
Of course, the biggest decision is Hamels. The Philies have drafted and developed one of the best young pitchers in baseball. They recently signed Cliff Lee to a five-year, $120 million contract, which Hamels plans to exceed.
Amaro is asked if it's as simple as not being able to reach an agreement with Hamels and trading him.
"Again, we think that we're contending," he said. "We're going to contend probably better with Cole than without Cole. Nothing necessarily has to happen before the 31st."
And why does he think the Phillies will contend?
"Because we have talent," he said. "We have ability on the field."
And the fact they are 11 under .500?
"I don't think anybody is running away with any of the Wild Card spots right now," he said. "Right now it would be very difficult to overcome the deficit as far as Washington is concerned [in the National League East], but you never know."
Amaro said he hasn't crunched the numbers to see how the Phillies would need to finish for a good shot at the postseason. But even if the Phillies win two of every three games the rest of the season they would finish 87-75 (.537). The Braves currently hold the second Wild Card spot and are on pace for 88 wins. The Phillies would need to play at a remarkable pace the final two months of the season, hope the Wild Card leaders stumble and none of the other teams ahead of them in the Wild Card standings get hot.
"I stay away from that stuff," Amaro said of those projections.
"One game at a time, babe," he said.
The Phillies have nine games before the Trade Deadline. It should be fun.