That is the kind of trade the Phillies could seek this summer, although from the opposite perspective. Montgomery envisions a scenario in which the Phillies maintain competitiveness while replenishing a depleted pool of younger talent.
It is not a straightforward strategy for his general manager, Ruben Amaro Jr.
"There is no question in 2010 and 2011 that we tried hard to win another World Series," Montgomery said. "We went for pieces, and we gave up pieces for pieces. I don't think you'll see us do that right now. We're not that confident that we're that close; that we're missing one piece to do that. It would be silly to do so."
The Phillies, a rival executive said, will target top prospects close to the majors or young, productive major-league players for their crop of veterans. That is problematic, given how much money is owed to the Phillies' trade chips, combined with their ages and injury histories. Montgomery said the Phillies are willing to assume money in a trade. Few teams, though, will agree to that exchange.
"We would much rather take the financial risk than the talent risk," he said. "That's where we find ourselves today. But we're not unique in that, either. Everybody is trying to lock up their young talent and hold on to it."
That, again, circles to the issue of procuring young talent. The Phillies have not drafted well in recent years. Many successes - like the package shipped to Houston - were sacrificed in the name of contention. Montgomery did not endorse the idea of an Astros- or 76ers-like rebuilding process that would require years of a grim product as a means to an end.
Attendance matters to the bottom line. "Does it cause you to say, 'We just don't want to play all young kids and get rid of everybody for fear we win 60 games'?" Montgomery said. "Yeah, that's a factor."
The Phillies, then, are stuck between contention and rebuilding. "We've seen that clubs have been able to do it effectively, quickly," Montgomery said. But, he admitted, teams cannot buy success in baseball like they did a decade ago. The most effective, albeit inefficient, method is through the amateur draft and international signings. That requires time.
"We knew when we had a nucleus of players - as talented as they all were, but sadly all happened to be within 18 months of the same age - that there would come a period of turnover," Montgomery said. "If you have enough talent in the minors to immediately put toward a new nucleus, perhaps you could do that turnover quickly. But we don't have that depth right now.
"We're trying hard to get where we have some nice pieces. We really like [shortstop prospect J.P.] Crawford. But an awful lot can happen. The beauty of having numbers - and this is why we still have hope for our young bullpen arms - the chance of getting two or three to actually succeed up here are a lot better."
Montgomery portrayed a franchise torn between alienating its fans who provided unprecedented support and one that understands it can no longer cling to the past success of its roster. It is an unenviable position, just one reason why Montgomery is often drawn to the Pence trade from three summers ago.
"Ruben alone didn't decide we were going to send four people to Houston for Hunter Pence," Montgomery said. "We all looked at it. We said, 'What do we need? We're short in one area. We're winning the most games we've ever won, but we didn't have comfort in right field or with a righthanded bat.' So we did it.
"Once you've done it, looking back, were we pushing the envelope? Yeah. Did we decide to push the envelope? Yeah. We did. Pat Gillick said, 'How silly was I to trade Gavin Floyd and Gio Gonzalez for Freddy Garcia?' That happens in this game."
The Phillies, however, cannot afford similar mistakes this summer.