Should he find somebody to play second base or third base while Chase Utley and Placido Polanco are out? Should he find more pitching instead?
"I'm always more concerned about the pitching," Amaro said before Tuesday's game against the Braves at Citizens Bank Park. "That never ever stops. At the end of the day, our team, offensively, should be able to handle the loss of a couple of these guys. It's difficult, but with the talent that we have, offensively we should be able to absorb that. But you can never have enough pitching, especially when you're trying to contend."
Utley will miss approximately seven more weeks following Thursday's surgery to repair a torn ligament in his right thumb. Polanco will miss approximately two to three more weeks with inflammation in his left elbow.
When Utley broke his right hand on July 26, 2007, the Phillies acquired second baseman Tadahito Iguchi the next day. So far, the Phillies have not found replacements for Utley or Polanco.
"I'm not as good as [former GM] Pat Gillick," Amaro said, poking fun at himself. "I'm just not as good as he is."
There has been speculation that the Phillies could add anyone from Ty Wigginton to Kelly Johnson to Mike Lowell to Miguel Tejada, but one source indicated that the asking prices have been extraordinarily high, as teams believe the Phillies are desperate enough to part with a top prospect for temporary help.
"We've talked to several clubs on many different fronts, not just addressing that particular issue," Amaro said. "We've talked to a lot of clubs about some other possibilities, too. We've been pretty proactive. Trades are not easy, and acquiring players is not easy. We have to assess what our needs are going to be two or three weeks from now, too, because we're going to get Polanco back. The prognosis on him is pretty good. Chase is going to get his stitches out in a couple of weeks, and in five weeks, he'll be doing mobilization stuff.
"While it's going to be a while, and it's going to be a big blow to us, the way the guys have played so far, we may have a totally different need come July 31 than adding a piece in the infield."
Amaro prefers pitching, which makes him no different from former Phillies general managers Ed Wade and Gillick, who always said they could never have too much pitching.
Amaro had the extra arm in December, when he traded Cliff Lee to the Mariners for prospects. Amaro was asked if he is kicking himself now that he is looking for pitching help.
"If we had Cliff Lee, we wouldn't have Roy Halladay," he said. "It's pretty simple. Time and circumstance dictate some of the things you can and cannot do."
In what way?
"We just felt like we were in a position to be able to hold one guy and not hold on to the other guy," he said. "We had to put ourselves in a position not to leave our club and our organization with the cupboard bare. By moving all of this talent from our organization, it just made it very difficult to continue doing business long-term."
Amaro thinks he has enough left in his cupboard to add pitching. Asked if that would empty the cupboard again, thus defeating the purpose of trading Lee in the first place, he said, "It depends on the deal I can make."
He would also consider trading a player from the 25-man roster.
"Obviously, I don't want to weaken my club, but if I have to weaken one area to strengthen another, I might do that," he said.
Amaro declined comment about reports that the Phillies have looked into the market for right fielder Jayson Werth, who will be a free agent after the season.
But if the Phillies do trade somebody from the big league roster, the most likely position would be outfield, because they have depth there and have a player waiting in the wings -- Triple-A Lehigh Valley's Domonic Brown, who is hitting .405 with four home runs and 11 RBIs since his promotion from Double-A Reading.
"Could he help us?" Amaro said of Brown. "Possibly. But again, it's only been 12 games. He's making a good impression. The players dictate their progress. He's dictating it."
Amaro declined to say if he would consider trading Brown to land pitching help, but trading Brown would have to have a big payoff. It is worth noting that the Phillies have been scouting Lee's past few starts, although it would be a hard sell to fans to trade Brown for Lee unless the Phillies could sign Lee to an extension.
Amaro said that at this point, Brown simply needs more experience.
"I don't think he'd be over his head," he said of a possible promotion to the big leagues. "But being over your head and being a productive Major League player are two different things."
The Phillies are looking for two things right now -- pitching and infielders -- and they have less than a month to decide what they need and how to make it happen.
Todd Zolecki is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.