Which raises the question again: What's former Cubs president Theo Epstein up to these days?
The question of whether Epstein could be an answer for the Bears front office came up as soon as he resigned from the Cubs in November 2020, with some Bears fans jumping on the idea.
It became such a topic locally that former Cubs manager Joe Maddon was asked about it by Chicago media during the virtual 2020 Winter Meetings access.
"He's won three World Series," Maddon said of Epstein in December 2020. "Yeah, he's ready for a Super Bowl."
Whether Epstein would take the now open Bears job is unlikely at best. But Maddon, who won the historic World Series during a five-year run as Cubs manager under Epstein, was asked over a year ago about what Epstein might do next in his career after resigning from the Cubs.
"Whatever he wants to do, whether it’s something within the baseball industry, whether he wants to be something in politics, if he wants to get into private-sector business wise — there isn’t anything he can’t do," Maddon said. "I believe that."
Wide-ranging media speculation of what could be next for Epstein included at the time the possibility he could fix what's ailed the Bears for over a decade.
Since leaving the Cubs, he's become a consultant in MLB's commissioner's office and an executive in residence for Arctos Sports Partners, which reportedly has its eye on eventual team ownership.
Maddon laughed a little at the Bears question, but seemed serious about his belief that Epstein would succeed in any walk — Bears and NFL included.
"DePodesta's broken the glass ceiling with that, right?" said Maddon, referring to Paul DePodesta, a former MLB executive who later became a Browns executive. "We’ve already had some crossover."
Epstein won two World Series during his nine-year run as Red Sox GM, including breaking the Curse of the Bambino in 2004. He took over as Cubs president in October 2011 and snapped their 108-year title drought in 2016.
"He could pretty much place himself in almost any situation and succeed at it," Maddon said. "His attention to detail, his ability to process and think things all the way through are incredibly different.
"He could literally do anything he wants, as long as the marriage is there, the match is made with whatever the organization may be. If he’s motivated to want to do it, he’ll kill it."