This year, Amaro arrives at the winter trade show as the GM of the .500 Phillies, a team in need of repair. He has already watched the two division rivals that finished ahead of the Phillies last season fill the same center-field need that they have.
They were outspent by the Atlanta Braves for free agent B.J. Upton and outmaneuvered by the NL East champion Washington Nationals, who acquired the talented and relatively inexpensive Denard Span in a trade with the Minnesota Twins.
There's plenty of time for Amaro to recover. It's early in the second quarter of this offseason, and the Phillies are down by only two. But with the emergence of the Nationals and resurrection of the Braves, Amaro's job has never been more difficult. Add in that the Los Angeles Dodgers are about to get $6 billion to $7 billion in local TV money, and it's conceivable that the Phillies will not even be the National League spending champions by the time this offseason is over.
"Even before last season, I was well aware of how good the Nationals and the Braves and the Marlins were going to be," Amaro said. "This division is not going to get any easier. It's going to continue to be tougher and tougher to keep up with the Joneses. That's the beauty and the challenge of the job."
Phillies president David Montgomery has said many times in the past that professional sports are cyclical. He believes that the gravitational pull of age and drafting lower will eventually take down whatever teams are on top.
That doesn't mean anything less than a National League East title is expected from Amaro in 2013. The general manager still believes a few good offseason moves mixed with some good fortune on the health front can lead to a sixth division title in seven years and possibly something more.
Amaro also believes that Philadelphia remains one of baseball's most attractive destinations.
"Clearly, I view our club and team as a great destination for any player," Amaro said. "We have the best fan base in baseball. I believe we have the best ballpark in baseball. I think we have one of the best atmospheres in the game. I think we have as good a clubhouse as there is in baseball. If I was a free agent, I'd be very happy to play for the Phillies."
That's a great sales pitch. Add $100 million to it, and the Phillies could end up with the centerfielder, third baseman, and eighth-inning reliever they need. Amaro, like any general manager, would love to fill those needs at a much lower cost to maintain some payroll flexibility for the future. In order to do that, he will have to pull off a trade like Washington general manager Mike Rizzo did for Span.
Regardless of what Amaro does or does not do to fill the Phillies' needs this offseason, the team's success or failure will ride just as much, if not even more, on how Chase Utley, Roy Halladay, and Ryan Howard rebound from the injuries that stripped them of playing time and success last season. If they're not right, the Phillies will not be either.
"I think what they do will be more significant than anything I do during the offseason," Amaro said.
Too old is how some see the Phillies, especially when they look at the Nationals and Braves. That's not how Amaro sees his team.
"[Yankees general manager] Brian Cashman made a comment about players who are older," Amaro said. "He said, 'I don't care about old, I care about good.' I agree with that. It is my hope that both Doc and Utley have great years this year and we extend them. Same with [Carlos Ruiz]. How long we extend them depends on what we have coming behind them. I think these guys can continue to be productive players."
As a Philadelphian, Amaro knows what will happen if he is not successful in his quest to keep the Phillies among the teams at the top.
"We have been extraordinarily fortunate to have players here who grew up in our system and players we have added to our team that the fans identify with in a positive way," he said. "But the reality, which I understand because I am a Philadelphian, is that the fans will get unruly if things start to go the other way. That's how it works here."
Contact Bob Brookover at email@example.com, and follow on Twitter @brookob.