With The Going About To Get Tough Again, The Cubs’ Theo Epstein Telegraphs His Exit…Again

Theo Epstein, a two-time drought-buster who is bound for the Hall of Fame the moment he becomes eligible, should be the executive you want running baseball operations for your favorite team.

He also proved yet again Tuesday, when he and the Cubs announced he would exit as the president of baseball operations with a year left on his contract, that he’s the executive you should want sitting across from you at a poker table.

While this got the jolt-you-upright-with-a-breaking news-alert-on-your-cell-phone treatment from the major sports sites, Epstein’s departure marked his third telegraphed major career move and should have come as a surprise only to those who had spent the last two months immersed in election-related doom-scrolling.

Following the Cubs’ sweep at the hands of the Marlins in an NL wild card series, Epstein once again displayed the PR training he otherwise pretends he never received by carefully making it clear he was both fully committed to the Cubs and also not planning to remain in Chicago much longer.

“I woke up this morning thinking about how we can improve for next year and position ourselves for long-term success,” Epstein said Oct. 5. “But given the things I’m on record with about the benefits of change at a certain point, it just means that you have to be smart in discussing the timing and nature of a transition because it’s inevitable at some point.

“My expectation is that I’ll be here. And my expectation also is that I’m going to do whatever is best for the Cubs everyday. 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.”

Those words — as well as Epstein’s latest namedrop of Bill Walsh and the late Hall of Fame football coach’s belief that executives shouldn’t remain in the same place for more than a decade — should have sounded familiar to anyone who remembers how Epstein’s Red Sox tenure began ending in 2011.

Rumors flew throughout the season that new Cubs owner Tom Ricketts would pursue Epstein even though the latter was only in the penultimate year of his deal with the Red Sox. Epstein finally addressed the speculation in…you guessed it, a very careful fashion that made it clear he was both fully committed to the Red Sox and also not planning to remain in Boston much longer.

“I know there are a couple of articles which have appeared, but I’m completely focused on the Red Sox of 2011, first and foremost, and what potentially lies ahead for this club,” Epstein said in comments that appeared in The Boston Globe on Sept. 1, 2011.

Later, Epstein insisted he was “…really happy to be with the Red Sox” and “…really happy to have the ability to come to work to a place like this” while also underlining his complete commitment to the team’s present and future.

“We spend all of our time trying to make this the organization we want it to be, building for the future, maximizing competitiveness for this year,” Epstein said. “Anyone associated with the Red Sox would be happy to work here and I am.”

The late Nick Cafardo, who wrote the article, noted Epstein “…never said he wasn’t interested or that the speculation was nonsense.” And sure enough, two months later, after one of the most stunning collapses in baseball history and the squeezing out of two-time World Series-winning manager Terry Francona, Epstein was working for the Cubs and beginning the rebuild that led to their long-awaited championship in 2016.

Remarkably, it was the second time Epstein telegraphed his intentions with the Red Sox. Epstein’s tenure as the Red Sox’s general manager appeared to end on Halloween night 2005, when he resigned following a power struggle with team CEO Larry Lucchino and bolted Fenway Park in a gorilla costume (you have to admit, as far as surprise career moves go, that’s a tough one to top).

But Epstein — and his high-powered friends in the Boston media — did little over the next few months to discourage the notion that he and the Red Sox were merely on a break. The spate of radio interviews Epstein did on Jan. 6, 2006 were ostensibly to promote his upcoming charity concert, but he spent most of his time talking about what the Red Sox did over the winter. He was back as general manager 18 days later.

As Epstein prepares to leave a second job after nine years at the helm, it’s worth noting that almost a third of his soon-to-be-former peers have served as their organization’s head baseball decision-maker for at least a decade. The likes of Billy Beane, Brian Cashman, Ken Williams, Dayton Moore, Jon Daniels, John Mozeliak and Mike Rizzo have enjoyed some of the highest highs (not quite the highest, in the case of Beane and Daniels) and then stuck around for the challenges that inevitably crop up after a period of success without having to use Walsh’s words to dress up and explain away their restlessness, impatience or tortured artist syndrome.

Nor does another legendary football coach. Upon his return to the Red Sox in 2006, Epstein said he’d like it if the team dispensed information in a manner similar to that of the Bill Belichick-led Patriots, who operate sans leaks and as if every morsel of information is a matter of global security. Except no one knows how long Belichick’s contract is, or if he ever wanted to go back and try to coach the Giants, or if he’s butting heads with Robert Kraft, or anything, really.

What we do know is that Belichick, now in his 21st season as the Patriots’ head coach, decided to oversee something approaching a rebuilding project when the going finally got a little tougher this year for the Tom Brady-less Pats. And while Belichick is a surprisingly prolific letter-writer, we can also be confident that if he ever leaves the Patriots, he won’t write a letter to his “Patriots Friends” that gets magically leaked to the biggest writers in the business.

The news of Epstein’s impending departure serves as a reminder that despite his dismissive comments about the sound and fury of baseball coverage in Boston, Epstein has always been obsessed with and keenly aware of what is said and written about him, as well as fiercely protective of what he views as his legacy.

It’s why he bolted the Red Sox as they were headed towards what appeared to be a rebuilding process, and why, despite working for the Cubs, he suddenly became available for interviews about the World Series-winning Red Sox following the 2013 season (to be fair, the 2013 Red Sox won it all with a core drafted and developed by Epstein).

The Cubs seemed primed to become a dynasty when they ended the 108-year drought by winning it all in 2016 with a homegrown core of position players younger than 30. But they’ve won just one playoff series since and are, at the very least, approaching a crossroads as Ricketts cries poverty and Kris Bryant, Anthony Rizzo and Kyle Schwarber all prepare to hit free agency after next season.

The player development pipeline appears dry for the foreseeable future. There were four Cubs on FanGraphs’ top 120 prospects this year — infielder Nico Hoerner, who used up his rookie eligibility in 2020, and three players who have yet to appear above Single-A. In addition, pitchers drafted and developed by the Cubs have made a grand total of 12 starts for the big league team during the Epstein era.

So it was a good time for Epstein to put to good use his old PR skills and plot his exit, even if there was no obvious new resume-burnishing destination awaiting him. The closest thing to a white whale in baseball today might be running the Angels, where someone gets the task of figuring out a way to build a championship contender before Mike Trout proves mortal. But not only are the Angels managed by Joe Maddon, whom Epstein ran out of Chicago last year, they just hired Perry Minasian as their general manager.

Epstein’s letter to his friends was couched in terms that gave him a familiar amount of wiggle room, but it seems likely he’ll actually sit out next season before figuring out his next destination. Whatever and wherever it is, history suggests he’ll probably make sure we all know it’s coming.