"He's done an outstanding job for the organization," Montgomery said. "I remember at the time we hired Ruben, I said I thought he had a situation where he had been excellently prepared for this opportunity, and I think, in my judgment, he's exceeded the expectations we had for him at that time."
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Amaro begins his third season as Phillies general manager. He enters 2011 after assembling what many think could be the greatest pitching rotation in more than a generation.
"I think he's exhibited sound judgment, and when Ruben is building a case for something, believe me, he's well prepared," Montgomery said of notable acquisitions like Roy Halladay, Cliff Lee and Roy Oswalt. "He indicates -- and I'm sure with help from his baseball [operations] people -- the logic behind those moves. We had a tough time explaining one of those a year ago, but the good news is we reacquired Cliff, so we don't have to explain that one anymore. But I think the reality is Ruben has always been a thinker and by nature he's aggressive. I think in this situation it's a good combination."
This is the longest contract Montgomery has extended to a general manager. Former general manager Ed Wade had an "evergreen" deal, which meant it automatically renewed at a certain point every year. Former general manager Pat Gillick signed a three-year deal when he replaced Wade in November 2005.
Amaro had a similar setup as Wade. His contract already had renewed for 2012, but Montgomery tacked on three additional years.
"It made sense, primarily for the continuity," Montgomery said. "I think we just feel right now we're very fortunate to have Ruben, but also the group of people that are surrounding him. It seemed to make sense from the club perspective to demonstrate to the clubhouse, to the staff and to the entire baseball operations group that he's the leader for the foreseeable future."
Amaro worked with Wade as assistant general manager from 1999-2005. He worked in the same capacity for Gillick from 2006-08. Amaro and former assistant general manager Mike Arbuckle had been the top two candidates for the job when Gillick announced he would not return.
"As Pat became firm in his resolve to step down after 2008, we engaged in numerous discussions, and I asked if he was still consistent in his thinking that he thought his replacement could come from within and he was," Montgomery said. "He left the choice up to me, which I understand. He did have some input on that, but I would say we felt that having been our assistant GM at that point for 10 years ... we really thought that Ruben had the characteristics to provide us with the best opportunity going forward. We think we made the right choice."
Amaro has acquired four 20-game winners since he replaced Gillick in November 2008: Halladay, Lee, Oswalt and Pedro Martinez. He has acquired players like Raul Ibanez, Placido Polanco, Jose Contreras and Chan Ho Park. Of course, not all of Amaro's moves have worked. No general manager is perfect. Despite the fact Lee is back, fans always will criticize trading him to the Seattle Mariners in the first place in December 2009.
Amaro has been asked if some of those moves, which have cost the Phillies young talent like Kyle Drabek, have been geared to maximizing a shrinking opportunity to win another World Series.
"That's part of it, but it's also about extending that window of opportunity," Amaro said. "We have talked about that a lot, and one of the reasons why we made that move regarding Cliff before is trying to make sure we extend that window. With all the moves that we have made as far as bringing in all these talented pitchers -- we didn't do it for just one year. We tried to extend it so we have success over a longer period of time, and that's the trick. I can't sit here and say we can't be a contender every year, but we're going to work to do that."