For 17 years, it would have been Montgomery in the spotlight. In his role as team president, he was ultimately responsible for every significant move the organization made. That was before he was diagnosed with jaw cancer last year.
Montgomery underwent successful surgery last year, and he eventually became chairman of the team. Then, Pat Gillick filled in, and, at midseason this year, MacPhail was hired to replace Gillick at the end of the season.
Montgomery, who received The Jamie Moyer Legends Award, as well as the Moyer Foundation's Community All-Star Award on Tuesday at the Crystal Tea Room, said the transition has gone smoothly.
"A year ago, I would have said very difficult. But the reality is I feel very, very good about Andy MacPhail," Montgomery said. "I think he's the ideal person. He clearly has the confidence of our ownership group. He has more left in his tank than I would at this stage. I turn 70 [next year]. I can't ignore that. I'm a healthy guy, but I have a different physique. I can't... be out on what I call the circuit as much.
"What I'm pleased about is [that MacPhail] feels very refreshed. He's had the three years off. Now he feels, 'Hey, time to get going.' He sees this as a challenge he's very capable of doing, because a) he's done it before, and b) it's easier to do in Philadelphia than it is other places because we have some resources that aren't available in every market. He's a planner. He's very thoughtful and I think he'll do an excellent job for us."
The decision to replace Amaro was especially difficult because Montgomery selected him to replace the retiring Gillick as general manager after the Phillies won the 2008 World Series. But it also underscored the point that his position has changed.
"All the emotions you can imagine," Montgomery said. "[But] it ran its course. And in order to give Andy the opportunity that we're talking about, we knew he needed a fresh canvas to work with. Sadly, that included Ruben. But it doesn't mean we shouldn't be respectful and appreciative of the work Ruben did because it was what we were trying to do."
Montgomery was instrumental in the decision to bring Ryne Sandberg back to the organization that originally signed him, which eventually led to Sandberg replacing Charlie Manuel as the Phillies manager in 2013. Sandberg stepped down earlier this season.
"That one surprised me," Montgomery said. "We went out to dinner afterwards and had a nice conversation. I couldn't believe some of the weight that he felt going into this year. I think, in a way, his opportunity [managing Triple-A Lehigh Valley], which made him attractive to us, and the way he handled people there and his clubhouse, I think he thought he could more easily transfer to a big league clubhouse.
"And he came at a very awkward time, if you think about it. We had this aging core of veterans who were anxious to continue to play. On the other hand, we had young people who wanted to play. And that doesn't always make for the easiest situation."
With Montgomery as president, the Phillies enjoyed the greatest run of sustained excellence in franchise history: five straight divisional titles, two pennants and a World Series championship. Now, others will supervise the current rebuilding process. But he has no regrets.
"We pushed it hard. We were all involved in trying to get one more after we got '08. We were all in. We knew the risk," Montgomery said. "When you trade your near-ready Minor Leaguers, there's going to be a dip. Now, to be honest with you, did we expect it to hit us quite as hard? No.
"But nobody could have expected at 2012 Spring Training that [Ryan] Howard, who was supposed to be ready by May 1, came back when [July 6]? That [Chase] Utley, all of a sudden, his knees wouldn't let him play. Roy Halladay went from being superhuman to be human, just like that. And we went from 102 wins to 81 wins," Montgomery continued.
"With the benefit of a rearview mirror, 'What were you thinking? You should have figured it out sooner.' We knew what we were doing. It was a conscious decision. It didn't work."
Montgomery remains deeply committed to seeing the Phillies succeed. The only thing that has changed is his role in the process. And he's comfortable with that.