Report: Theo Epstein Meeting with Tom Ricketts to Discuss Future, Early Exit Possible

According to David Kaplan of NBC Sports Chicago, Theo Epstein and Tom Ricketts are meeting next week to determine the direction of the Cubs’ baseball operations department and Epstein’s role in it. This isn’t anything new in and of itself because it’s part of the annual end-of-season evaluation, but Kaplan added that it’s “virtually certain that Epstein will not seek to sign another deal.”

Again, not really much of a surprise since 2021 will mark Epstein’s 10th year with the organization, a milestone Epstein himself has said in the past is long enough for an exec to be in the same role. He’s always seemed destined for something bigger, or at least different, and he’s probably not super jazzed about trying to remake the organization for a second time.

I’m not talking about another rebuild, mind you, but there’ll have to be an overhaul following the exodus of some current core players and the advent of a new CBA. As such, Kaplan writes, it’s possible Epstein and ownership could negotiate an early exit.

So either Epstein essentially hands over the reins to Jed Hoyer and slowly backs away over the course of next season or he puts on his gorilla suit after Monday’s postmortem presser and peaces out to let Hoyer run the show. It may just come down to whether or not Epstein still has the patience for it, since it’s not like his right-hand man needs any on-the-job training in order to learn the ropes. Transitioning to Hoyer would likely be just as seamless on Tuesday as it would a year from now.

Most have assumed for quite a while that next year would be Epstein’s last in Chicago and Kaplan has suggested as much in the past. That was one of the topics discussed when he joined Cubs Insider’s The Rant web show back in May. But even if it’s long been fait accompli, having a definitive exit strategy makes things a little more real than they’d previously been.

For what it’s worth, I’d rather the Cubs make the move sooner if it’s going to happen after next season just so Hoyer or whomever they tab to run baseball ops can guide any changes this winter. Whatever ends up happening, Epstein’s legacy as the man who brought a World Series to the North Side of Chicago will endure long after he’s gone.