John Middleton is a devoted alumnus of Amherst College. He donates money, chairs a committee, and sits on the board of trustees. He even participated in the search for a president nearly a decade ago.

Now, as Middleton mulls the future of the Phillies' front office, he should consider planning a college reunion.

For a small liberal-arts school in central Massachusetts, Amherst has produced an oddly large cast of baseball executives. There’s Dan Duquette, former general manager of the Montreal Expos, Boston Red Sox and Baltimore Orioles; Neal Huntington, architect of the Pittsburgh Pirates' only three playoff teams in 28 years; Ben Cherington, GM of the World Series-winning Red Sox in 2013; Duncan Webb, Los Angeles Dodgers director of baseball resources; and Jared Banner, who has worked in player development for the Red Sox and New York Mets.

Duquette led the Orioles to four winning seasons and three playoff berths in seven years after replacing Andy MacPhail in 2011. At age 62, after two years out of the game, he’s said to be interested in running another team. With MacPhail set to retire from the Phillies presidency late next year, could Duquette follow him again?

Cherington, 46, heard from Middleton five years ago for the Phillies' last GM vacancy, but having just stepped down in Boston, he wasn’t seeking another front-office job. He got hired last year to rebuild the Pirates, coincidentally succeeding Huntington. If the Phillies offered a title bump from GM to president of baseball ops, might Cherington, highly regarded for his intelligence and integrity, be tempted to traverse Pennsylvania?

Two years after getting fired by the Baltimore Orioles, Dan Duquette (left) is said to be interested in another opportunity to lead a baseball operations department.
Gene J. Puskar / AP
Two years after getting fired by the Baltimore Orioles, Dan Duquette (left) is said to be interested in another opportunity to lead a baseball operations department.

Middleton has sought input from several advisers, including Hall of Fame former general manager Pat Gillick, but MacPhail said he’s urging the managing partner to play a “hands-on role" in selecting his successor. MacPhail also said the Phillies have “gone through the preliminary stages of a search” by compiling a list of candidates, though their timeline for making a hire remains a mystery within baseball.

It remains possible that MacPhail and interim GM Ned Rice will be in charge for the foreseeable future. With demoted Matt Klentak still getting paid and MacPhail under contract through next season – and given the steep revenue losses in 2020 and uncertainty over when a COVID-19 vaccine will enable fans to fill ballparks in 2021 – Middleton may deem this a bad time to add another well-paid executive to the payroll.

But it’s also a terrible time for the Phillies to take a gap year. They haven’t made the playoffs since 2011, and their best players – Bryce Harper, Aaron Nola and Zack Wheeler – are squarely in their prime. The National League East is more competitive, too, now that deep-pocketed Steve Cohen has taken ownership of the Mets.

So, if Middleton won’t pursue Duquette or Cherington, he would be wise to at least study their work, specifically Duquette’s 2011-12 offseason in Baltimore and Cherington’s 2012-13 in Boston.

The Orioles finished last in 2011 but had a core of center fielder Adam Jones, shortstop J.J. Hardy, catcher Matt Wieters, first baseman Chris Davis and right fielder Nick Markakis. Without making a splash in free agency, Duquette improved the rotation by trading for Jason Hammel, signing Wei-Yin Chen from Japan and picking up Red Sox castoff Miguel Gonzalez. He also assembled one of baseball’s best bullpens.

The result: The Orioles went from 93 losses in 2011 to 93 wins and a wild-card berth in 2012.

Pittsburgh Pirates general manager Ben Cherington built a World Series winner with the Boston Red Sox in 2013.
Keith Srakocic / AP
Pittsburgh Pirates general manager Ben Cherington built a World Series winner with the Boston Red Sox in 2013.

A year later, the Red Sox had a long list of needs after a last-place finish. But rather than stalk star players, Cherington signed mid-market free agents at catcher (David Ross), first base (Mike Napoli), shortstop (Stephen Drew), left field (Jonny Gomes) and right field (Shane Victorino), and in the rotation (Ryan Dempster) and bullpen (Koji Uehera).

The result: A worst-to-first turnaround and six-game World Series triumph.

How does that apply to the Phillies? Their myriad needs include remaking a historically bad bullpen and adding another starting pitcher. Unless they commit to Adam Haseley, they must address center field. And if catcher J.T. Realmuto and shortstop Didi Gregorius leave as free agents, they’ll need to be replaced.

It seems doubtful that Middleton will maintain this year’s franchise-record payroll of nearly $207 million, as calculated for the luxury tax. But how much will it be reduced?

Between Realmuto, Gregorius, Jake Arrieta and David Robertson, the Phillies have $60.5 million coming off the books. If they reinvest 75% of that – and even that may be ambitious – they would have $45 million to spend on 2021 payroll. Re-signing Realmuto could eat up about $25 million. Star reliever Liam Hendriks could cost another $10 million to $15 million.

But what if the Phillies focus on James McCann, the second-best available catcher? Perhaps they could then scoop up at least two veteran relievers (Brad Hand, Alex Colome, Shane Greene, Trevor May and Trevor Rosenthal are available in a flooded free-agent market) and a buy-low starter (Garrett Richards or James Paxton, for instance).

And if middle-class free agents feel the pinch of the pandemic as much as most industry observers expect, there might be money left over to address center field and/or shortstop, too.

Maybe Rice – guided by MacPhail in his swan song – is up to the challenge. If not, Middleton need only look to his beloved alma mater’s alumni directory to find a few people who have done it before.