The Chicago Cubs' announcement on Tuesday that president of baseball operations Theo Epstein would be stepping down from his role on the team with a year left on his contract creates a series of questions. What will the future bring for the ballclub? And for Epstein? We turned to senior baseball columnists Buster Olney, Bradford Doolittle, Jesse Rogers and David Schoenfield for their assessments of the situation now that the architect of the 2016 World Series champs is stepping down.
Now that Theo Epstein has stepped down, what do you expect to see from the Cubs the rest of this offseason?
Buster Olney: Massive turnover. The Cubs have signaled to other teams they are going to alter the core of position players that won the World Series in 2016 and they're open to talk about everyone from Yu Darvish to Javier Baez. The perception of other teams is that the club is dealing with major financial stresses.
Bradford Doolittle: Everything points to the Cubs aggressively pushing to reduce their payroll commitments for 2021, with the most obvious avenue for doing that being a Kris Bryant trade. It's not a great time to be shopping a player expected to get somewhere in the range of $18 million to $20 million through the arbitration process, but Bryant can be a tipping-point player for a team willing to take on the money. The Cubs also could non-tender Bryant, but that decision would fall somewhere between outrageous and obscene. Moving Bryant would create some wiggle room to allow the Cubs to possibly fill in some gaps for their 2021 roster. After that, they need to continue to work toward an extension with Baez.
Jesse Rogers: Nothing has changed for the Cubs with or without Epstein. They still have massive payroll/cash flow problems and a core group of players on offense that has stalled. But it's not like Epstein is turning things over to a new regime. Jed Hoyer will pick up where they both left off: attempting to turn over a roster that might not net the Cubs much on the trade market while also rebuilding the back end of their starting staff in the pitching rotation.
David Schoenfield: How about a "soft" rebuild? Given that many organizations might be dealing with major financial stresses, trading high-salaried players might not be easy. But consider as well that the National League Central is ... well, it's very winnable. The Cubs actually won the division in 2020. The Cincinnati Reds are going to lose Trevor Bauer. The St. Louis Cardinals need to find an offense. The Milwaukee Brewers are unlikely to make any big additions and could trade Josh Hader. If they play a 162-game season in 2021, it might take only 85 victories to win the division. The Cubs could do a partial teardown and still compete.
Which current star are the Cubs most likely to trade this winter?
Olney: One way or another, I expect them to move on from Kris Bryant. He'll be making a lot of money for next year, and given the team's desire to cut payroll, he could move.
Doolittle: Seems pretty clear it's Bryant. He is one year from free agency, he has Scott Boras for an agent and the Cubs have a passable replacement on hand in David Bote.
Rogers: Willson Contreras is the one guy who can bring back a nice return for the Cubs, and they aren't in a position of luxury around the diamond where they can keep two competent catchers. Victor Caratini already catches Yu Darvish and was a DH in 2020; there's no reason Caratini can't have a bigger role while the Cubs get some talent back for the ultra-talented Contreras. While Bryant is a name to watch as well, his price tag -- as compared to Contreras' -- doesn't make him as easy to deal.
Schoenfield: While Bryant appears most likely to leave, he isn't going to extract much trade value given his salary. If the Cubs feel their biggest need is to bring in young talent as opposed to just dumping salary, the most valuable trade asset they have is probably Kyle Hendricks -- a consistent, underrated pitcher making $14 million in each of the next three seasons. And don't rule out the possibility of trading Javier Baez. Next year's free-agent class is loaded with shortstops -- Francisco Lindor, Trevor Story, Corey Seager -- and given Baez's poor 2020 season, the Cubs might feel they'd rather make a push for one of those players in 2022, rather than bank on Baez bouncing back.
How much do you think the way the Cubs' front office operates will change under Jed Hoyer?
Olney: First and foremost, the Cubs will be doing some rebuilding -- and the fact that the organization has signaled this will make it easier for Hoyer to be aggressive.
Doolittle: It's hard to see it changing much, only it will be Hoyer with the final say-so. It will be interesting to see how the various job titles evolve among Jason McLeod, Dan Kantrovitz and the rest. I also will be curious to see if the Cubs bring in a new voice for the front office in some capacity, perhaps someone Hoyer has worked with in another context.
Rogers: Their styles are different, but Epstein and Hoyer have similar baseball ideas. Agents often say Epstein has the shorter fuse but Hoyer is no less effective. It's hard to imagine Hoyer taking a hard turn in a different direction after working so well with Epstein for so long.
Will Epstein work in baseball again? If so, in what role would you expect?
Olney: Yes. As one of his peers said: "Theo might have other interests, but he's a baseball guy."
Doolittle: In the letter he sent to friends and colleagues that was leaked, he said he expects to take on a new challenge with a team at some point, just not this year, and he added that he would like to be part of an ownership group.
I will admit, a scenario immediately leapt to mind. If Epstein plans to stay in Chicago as his primary residence, well, White Sox owner Jerry Reinsdorf is 84 years old and it's not believed that he plans to turn the club over to his children upon his death. Well, the Veecks moved from the north side to the south side, so why not the Epsteins? I've been saying for years that given the development patterns in Chicago, the White Sox are a sleeping giant, and who better to bring that theory into fruition than executive and part owner Theo Epstein?
Rogers: Yes, there's no doubt. He has already stated he wants to run another team. Ownership makes some sense, but as long as he has final say in baseball decisions, it might be all he wants. Taking over a third losing franchise isn't out of the question. Like his first two tries, he'll have only one direction to go: up.
Which drought-busting title was more impressive: 2004 in Boston or 2016 in Chicago?
Olney: The Cubs' win in 2016, because that team was built from the ground up. When Epstein took over the Red Sox, they already had Pedro Martinez and Manny Ramirez, two huge building blocks.
Doolittle: It's Chicago. The team's processes were completely out of step with the times when Epstein took over, the Cubs were old and expensive and there was zippo in the pipeline. He tore the team down to bare bones and built the Cubs up from scratch.
Schoenfield: Yeah, definitely the Cubs. The 2002 Red Sox, the last pre-Epstein team, won 93 games. Give Epstein credit for putting the final touches on the organization -- such as signing David Ortiz and having the guts to trade away franchise icon Nomar Garciaparra in 2004 -- but he took over a winning franchise. The Cubs were a complete mess, having lost 91 games in 2011 with the sixth-highest payroll and a farm system in which four of the top five prospects were Brett Jackson, Matt Szczur, Trey McNutt and Dillon Maples. (Baez was the fifth.)
Rogers: Epstein would even say the Cubs because he built that 2016 team from the ground up. In fact, his 2007 championship in Boston might qualify for the same reason. In 2004, Epstein inherited what was left from the past regime and finished the job. In 2007 and 2016, his fingerprints were all over every aspect of those championship rosters.
What will you remember as the signature Epstein front-office move for the Cubs?
Olney: The signing of Jon Lester -- the addition of the perfect player at the perfect time, as Epstein knew, because he'd had Lester in Boston.
Doolittle: I guess for me it goes back to the beginning, when the Cubs traded Andrew Cashner to the San Diego Padres for Anthony Rizzo. Rizzo was the cornerstone piece, and the team grew up around him. That's where it all started.
Rogers: The signature move was getting Lester to sign with the Cubs before the 2015 season. The two-time world champion at the time left more money on the table to join up with an organization synonymous with losing. Yes, there were more impressive/dramatic moves via trades and other means, but the no-nonsense Lester coming on board was the sign the Cubs were ready to win -- and they did.
Schoenfield: I agree with Buster, Brad and Jesse but will throw out the acquisitions of Jake Arrieta and Kyle Hendricks as two under-the-radar deals that obviously paid huge dividends. The "tanking" that allowed the Cubs to draft Kris Bryant and Kyle Schwarber helped, and Epstein signed the right free agents. But between these two trades and the Rizzo deal, he picked up three star players without giving up anything significant -- the kinds of moves that land somebody in the Hall of Fame.