Ever since the World Series Championship in 2016, the Chicago Cubs have pretty much stood pat in the off-season, with a few exceptions here and there. This winter will be no different.
The Chicago Cubs signed Yu Darvish in the 2017 offseason as well as Tyler Chatwood. Darvish was for six years and Chatwood for three years. Chatwood, like a few other Cubs, has his salary come off the books this winter, and the Cubs may finally have some money to spend again.
Jon Lester, who may have very well made his final start at Wrigley Field Wednesday, is a free agent, as is Jose Quintana, which frees up over $30 million at least. Just don’t expect the Cubs to do anything with this money.
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Theo Epstein’s contract is up after 2021. The contracts of Anthony Rizzo, Kyle Schwarber, Kris Bryant, and Javier Baez are also all up after 2021, barring no extensions. With the front office in doubt, as well as this core, it’s not inconceivable to think Epstein lets everything play out next year and then turn the impending rebuild over to whoever the new President/GM may be. He could also trade guys like Bryant, who has one year left on their original rookie deals, and see what the Cubs can get for the future.
The other side of the token for the Cubs where 2021 may be the last run for these guys, and Epstein may put all his chips in one last time and try to go out a winner. There is, of course, no guarantee that Epstein leaves the team, but what else does he need to accomplish in baseball? He may want a new challenge, and who can blame him?
Jed Hoyer’s contract is also up after 2021, so the Cubs could genuinely be looking at the end of an era. It all depends on how they want to approach the reckoning season next year, if they’re going to go for it or if they’re going to concede and just let things play out, or does Epstein extend his contract again and try to build the next contender in Chicago?
Given how the last two offseasons have gone, the best guess is no. They may very well stick with the same team and shed some salary where they feel it is necessary to kick off the rebuild early. Fans should come to terms with a rebuild sooner rather than later. When that many players leave in one year, there will be a transition period, regardless of the team.
The foundation for the next team is laid already, at least with Nico Hoerner and Adbert Alzolay getting some chances. Brennen Davis and Brailyn Marquez down at the alternate training site/minor leagues are another impressive duo that Chicago should be excited about. The foundation is there, is Epstein going to build on it one last time or let it lie?