2020 Offseason

If the Phillies are willing to wait, Theo Epstein could become available

Philadelphia Phillies managing partner John Middleton didn’t set a concrete timetable for the search for the replacement to Matt Klentak, and that could work in the organization’s favor if they choose to set their sights on one of the most accomplished executives in modern baseball history.

Theo Epstein is one of the most accomplished executives in baseball. (Ian Johnson/Icon Sportswire).

One would think that if an exit was imminent for Chicago Cubs president of baseball operations Theo Epstein, he wouldn’t have been allowed to speak to the media, which he did Monday morning. Matt Klentak didn’t get a chance to speak to the media after the conclusion of the 2020 season, because his future was in jeopardy and he was ultimately reassigned within the organization. Epstein did give a year-end address after the Cubs were upset by the Miami Marlins Monday, but his words did make you believe that he is closer to the end of his time with the Cubs than the beginning.

“My expectation is that I’ll be here,” Epstein said to the collective media, including 670 The Score, about this upcoming season. “And my expectation is also that I’m going to do whatever is best for the Cubs every day. That means being thoughtful about a transition, whenever that may come. But I’m focused on the 2021 Cubs and how to position ourselves for long-term success.”

Indeed, chairman Tom Rickets has since said that Epstein will return for the 2021 season, but also seemed to give you the sense it may be his final year in Chicago.

“I don’t think anything has changed from the perspective of what his responsibilities are,” Ricketts said to Bruce Levine of Marquee Sports Network. “He will continue to be the president of baseball operations and do the right things for the best interest of the ballclub through the end of his contract.”

Normally, Epstein would be worth monitoring, but your main takeaway would be that unless he was let go this week, the Phillies would have to move on. However, when discussing whether interim general manager Ned Rice is too similar in approach to Klentak to make key decisions, Middleton did leave the door open to the possibility that the Phillies don’t immediately hire a new front-office lead.

“If you’re talking about a permanent hire, that would be one issue. If you’re talking about something that could be two, three months – or at most, a season – that’s an entirely different kettle of fish,” Middleton said.

If the shortest timeframe for the Phillies hiring a new general manager is in two or three months, they may as well take as long as they need. In three months, J.T. Realmuto and Didi Gregorius will likely have made free-agent decisions. The Phillies will be deep in a plan on how to fix one of the worst bullpens in the history of the sport. If a new general manager (or whatever title they would have) isn’t in place by the start of free agency, which is just days after the conclusion of the World Series, you’ll be relying on Rice to be the No. 1 voice this offseason.

And this wasn’t a throwaway comment by Middleton. He values face-to-face conversations, one of the reasons it took over 10 days to make a decision on Gabe Kapler’s future last offseason. Making such an important hire could require even more time to deliberate in the COVID-19 world.

“We don’t really have a firm timetable,” Middleton admitted Saturday. “I think one of the things that’s really going to potentially play havoc with this offseason is COVID. Right now, our offices aren’t even open. So if you had somebody new today, they can’t go into the office to work…they can’t meet people…they can’t work with people.

“Holding Zoom meetings only goes so far, particularly when you’re talking about establishing relationships. What I’ve discovered over the last six months is Zoom is a pretty good way to have meetings with people that you know and that you have relationships with, but when you start introducing new people to each other via Zoom calls, it’s not nearly the same thing. So I think that’s going to play a factor in terms of our timetable. I think we have to be flexible and we have to be nimble. So we’ll go out and see.

“And who knows how COVID is going to play in potential candidates’ minds… whether they’re going to become conservative and say ‘I wanna stay where I am because I know where I am and I feel safe here,’ or whether they’re gonna say ‘I wanna take a chance and move out into a new job and a new organization.’ I can’t tell you.”

What will the Phillies look for in a successor to Klentak? Middleton cited how outside of the 1970s and mid-2000s, the Phillies have largely struggled with drafting and developing homegrown superstars. He said his ideal candidate will have a track record of success in the “acquisition and development of talent.”

Someone like Damon Oppenheimer, the vice president and director of amateur scouting for the New York Yankees, could be an interesting candidate. Proximity to Brian Cashman’s greatness can’t hurt your resume, and he has experience working with manager Joe Girardi and scouting director Brian Barber, which has to be considered here. What’s more, the Yankees have done a tremendous job, even without bottoming out, of finding elite talents in the draft and supplementing them with key free agent signings and trades.

Still, Oppenheimer has never been in charge of a front office before. Neither had Klentak when the Phillies hired him in 2015. Usually if a first-time general manager or coach is fired, they’re replaced with a veteran in that field. The Phillies did it last offseason by hiring Girardi after firing Kapler, and they may very well opt to go the proven route with Klentak’s replacement as well.

If so, Dave Dombrowski is available, though he seemingly didn’t leave the Detroit Tigers or Boston Red Sox in a great position for the long run. Epstein has produced World Series Champions in Boston and Chicago, at least in part because of developing internal talents.

The 2004 Red Sox were more of a team built with external additions, but the 2007 Red Sox core included Jon Lester, Dustin Pedroia and Jonathan Papelbon, all home-grown talents.

The 2016 Cubs included Kris Bryant and Javier Báez, two first-round picks, along with Anthony Rizzo, Jake Arrieta and Kyle Hendricks, all talents who didn’t begin to really hit their stride until being acquired by the Cubs organization.

In both places, Epstein made major signings and trades as well, some of which were hits and others that weren’t. His track record is far from perfect, but you’d struggle to find an executive, especially one that could be had, who has a perfect resume. Epstein’s track record features a lot more of a hybrid approach in big markets; sure, you’ll make some high-priced signings, but you’ll do that in addition to your homegrown nucleus, not in place of it.

Outside of Aaron Nola, Alec Bohm and Rhys Hoskins, pretty much every notable player that was on the 2020 Phillies was acquired either through a signing or a trade. That’s not a way to build a sustained contender. Sure, in the back-half of the 2007-2011 run, the Phillies acquired Cliff Lee, Roy Halladay, Roy Oswalt and Hunter Pence, but they already had grown a core that included Chase Utley, Jimmy Rollins, Ryan Howard, Cole Hamels, Carlos Ruiz and Ryan Madson.

If the Phillies were to get aggressive in a pursuit of Epstein, whether it’s this offseason or next, it would likely take installing him as the president, rather than the general manager. Seemingly that wouldn’t be an issue. Andy MacPhail’s contract runs through 2021, and it’s hard to believe the 67-year-old would stand in the way of bringing in Epstein if it meant a change in his role. If you listened to Middleton Saturday, it seems like the Phillies aren’t far from phasing MacPhail into another role anyway.

The bigger challenge may be to entice Epstein to Philadelphia. Other organizations will certainly show interest in his services, and it’s possible that he’ll simply want to take a few years off after extended runs in Boston and Chicago. At 46, Epstein could take four or five years off and still be in position to make another great run with another organization when he decides he’s ready.

Of course, money can change minds. Even as they’ve struggled to develop talents at a pace the pleases Middleton, the Phillies have attempted to level the playing field by flexing their financial muscle.

That muscle may not be as much in play this offseason, after a shortened 2020 season that didn’t include fans being allowed to attend games. Whether that reasoning pleases the fanbase or not, Middleton suggested that it could complicate keeping J.T. Realmuto, arguably the best player on the team.

Whether the deep pockets of the Phillies will be back in play a year from now – and whether they’d want to kick the can a year on hiring a new lead executive, which could mean wasting another year of the respective peaks of Bryce Harper, Aaron Nola and Zack Wheeler – is unclear. But Epstein has built sustained contenders in Boston and Chicago. At the very least, trying to lure him to Philadelphia is an option that the Phillies should consider.


  1. Who Will Be The Next GM Of The Phillies?
  2. Does John Middleton Regret The J.T. Realmuto-Sixto Sánchez Deal?
  3. The Phillies’ 2015 GM Candidates: Where Are They Now?
  4. Phillies Nation Top 20 Phillies Prospects
  5. Bryce Harper: ‘Pitching Wins Championships, Developing Wins Championships’
  6. Will Andrew McCutchen Be Phillies Everyday Left Fielder In 2021?
  7. Joe Girardi Still Views Scott Kingery As Starter, Predicts Bounce-Back Season In 2021
  8. Bryce Harper Sends Clear Message About J.T. Realmuto’s Future
  9. What Position Is Alec Bohm’s Future At?
  10. Phillies’ 2020 Walk-Up Songs

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