One of those trades helped the Phillies reach the World Series (Lee), another helped fuel the Houston Astros' rebuilding process (Pence).
With only two teams in baseball with fewer wins than the Phillies, Amaro understands his team is much closer to the latter. The embattled general manager is prepared to make a move (or several) if a team comes calling in the next 6 weeks.
"If we have to go backwards to go forward, then we're prepared to do that," Amaro said before last night's game at Citizens Bank Park. "We have our scouts out . . . seeing as many teams as possible. We're making sure we know which players we like the most in certain organizations and preparing for that. At the same time, we're continuing to assess what our needs are. If we have to go through the transition, we're preparing and evaluating what our needs are."
The Phillies' needs are many. Such is the reality of a last-place team with a glut of 30-somethings in its lineup and rotation, and a dearth of prospects in its minor league system.
Because of that, Amaro acknowledged there are no untouchables. He will listen to offers on anyone and everyone. Jimmy Rollins and Chase Utley, two pillars of the franchise, aren't excluded from that anyone and everyone.
"I mean, it's hard to speculate, because they are 10-and-5 guys," Amaro said referring to each player's 10 years in the big leagues and at least 5 with the same team, which gives them full no-trade clauses. "If someone comes and says we'd like to add Jimmy Rollins or Chase Utley, I have to do my job and listen. Explore. But the reality is it could all be wasted time. They may not want to go anywhere. And at that time, we may not want them to go anywhere either. So a lot of it depends on what we wanted to do, but most of it depends on what they want to do."
Utley just re-signed a multi-year contract extension with the Phillies 10 months ago, forgoing free agency. So it's uncertain whether he would suddenly change his mind and want to leave.
Rollins is deeply rooted in the organization and in Philadelphia at large. He joined the organization 18 years ago this month, his wife is from the area and his family makes an offseason home in suburban South Jersey.
Among other veterans on the Phillies' roster, including closer Jonathan Papelbon, outfielder Marlon Byrd and catcher Carlos Ruiz, salaries could be potential stumbling blocks to making trades happen. The dollars and years left on many of the veteran contracts might not be appealing to contending teams, and if a team does take one of those contracts, it would be less inclined to offer an attractive prospect in exchange.
But Amaro said there was a way around that hurdle, too.
"We've taken money back on deals before," Amaro said, "so we'll do it again if we have to."
Health is another issue, of course. A month ago, Lee and Mike Adams looked like attractive, trade-market commodities that could fetch prospects. Yesterday, Adams (rotator cuff) had a cortisone shot and won't throw for 10 days, and Lee (elbow) played catch for only the third time in the last 25 days.
A proven performer in the postseason, Lee would arguably be the best player the Phillies could move in an effort to get premium young talent back (which, admittedly, the front office already failed at accomplishing once with Lee). But the idea isn't feasible if Lee isn't healthy.
Could he return within the next month, and change that?
"I think so," Amaro said. "Cliff threw again today and it went well, which is good. Hopefully, he can start going in a straight line."
A lot can happen in the next month, though. Lee could have a setback. The Phillies could go on a win streak.
But, at least yesterday, Amaro was cognizant of the state of his team and was prepared to make changes, too.
"We have to see what happens over the next couple of weeks," Amaro said. "We have [Cody] Asche coming back, we're waiting on Cliff, our bullpen is starting to do something, you're seeing some of that growth finally.
"What's my confidence level? I believe in our players. But if they keep playing at the same rate they were playing, then my confidence would be low. But we'll see. They have ability. It's a matter if the guys put something more significant together."
Since Amaro is responsible for the team that's struggled on the field for the latter part of the last two seasons, it's also worth wondering whether he should be in control if ownership commits to rebuilding. It's a sentiments fans voice and Amaro hears regularly.
"I don't have any issues with my own job status," Amaro said. "I believe in what we do and what I do, and that's not my decision."
Tony Gwynn Jr. started in centerfield in place of Ben Revere, who is nursing a minor right thumb injury. Revere was hurt sliding into second base on Wednesday. Manager Ryne Sandberg said Revere was healthy enough to play, but he wanted to get Gwynn at-bats . . . Cody Asche (left hamstring) was scheduled to begin a minor league rehab assignment at Low A Lakewood yesterday. Sandberg said Asche would continue rehabbing at Triple A Lehigh Valley next week. Asche is not expected to rejoin the Phillies for at least another week . . . Ruben Amaro Jr. said shortstop prospect Roman Quinn might begin playing in centerfield. Quinn, 21, was the team's second-round pick in the 2011 draft. He returned to Class A Clearwater last month after rupturing his right Achilles' in October. Quinn, rated second-best prospect in the Phillies' system by Baseball America before the 2013 season, is hitting .253 with a .317 OBP in 19 games with Clearwater this season. He has 65 stolen bases in 152 minor league games.
On Twitter: @ryanlawrence21