With Cubs In Question, Epstein Hopes Team Answers

Theo Epstein spent much of Cubs Convention offering hope for this season.

Chris Emma
January 19, 2019 - 3:36 pm

CHICAGO (670 The Score) -- Secluded from sight in a far corner of the Sheraton Grand ballroom, Cubs president of baseball operations Theo Epstein grasped his cell phone tight. He tapped the thumbs, scrolled up and down, glancing up with each name of note read by the venerable voice of Pat Hughes.

Daniel Descalso, the biggest free agent added to date this offseason, was given a lukewarm welcome. Jason Heyward, owed $106 million in base salary over the next five years, received a mix of cheers and jeers. Yu Darvish, who started eight games due to injuries and was absent as the Cubs crumbled down the stretch last season, earned boos drowned out by Soulja Boy's "Crank That" blaring to a high volume.

For all the fanfare that comes to Cubs Convention each January, there was also a palpable feeling of unrest. Why haven't the Cubs opened the checkbook for a star free agent like Bryce Harper? Is this front office really content with a group that deserved to get beat in 2018? Will this championship window only bring one World Series?

So there sat Epstein alongside Cubs general manager Jed Hoyer, phone clutched to his hand, taking it all in the best he could. He understands the relative disappointment. He came ready to answer for it.

"It's a good thing," Epstein said Friday night, anticipating the sentiments of the weekend. "It's passion. It's expectations. It's raised standards. It's wanting to continue to be part of something special. We have fans who waited the better part of a century to be on top and love the way it feels up there and don't want to leave. We have that in common."

Last fall, the Cubs were caught by their upstart rivals from Milwaukee. A young Brewers team led by National League MVP Christian Yelich overcame a five-game deficit in early September to chase down the Cubs, whom they then buried in a Game 163 in Chicago. The Brewers celebrated at Wrigley Field, then the Rockies did the same the next night after ending the Cubs' season in the NL wild-card game.

On the morning of Oct. 3, only hours after it all ended for the Cubs, a sleepless Epstein returned to the team's office building in Wrigleyville and began looking forward. He held exit interviews with the players, gathering their feedback on the sudden and stunning end to their 2018 season and looking to find why it happened. Epstein felt it was the most honest and introspective his players have ever been.

"It's kind of good for us to go through that, get our teeth kicked in a little bit on our field in Game 163 and the wild-card game," third baseman Kris Bryant said to a group of reporters. "I think ultimately we'll all learn from it and come out with a chip on our shoulder."

With the realization that his Cubs wouldn't be much of a player at the free-agent table this offseason, Epstein drew inspiration from his players. He came to accept that the talented individuals he brought into the organization could come closer to their full potential with a sharper edge to each day.

As Epstein said last October, the Cubs didn't lose the NL Central in Game 163. It was lost in poor efforts in matinee games in places like Cincinnati or Miami earlier in the season. In turn, that put a brighter spotlight on manager Joe Maddon and his easygoing personality, which enables his players to accept losses they perhaps shouldn't. 

Maddon often cites the term "Meat Loaf "-- a nod to the artist with a 1977 song titled "Two Out of Three Ain't Bad" -- as validation to the results that didn't bring the Cubs enough. The 64-year-old Maddon is now working a lame-duck season as manager without a contract beyond 2019. It's one of many examples in how Epstein is seeking more urgency out of his Cubs.

As Winter Storm Harper blew snow throughout downtown Chicago on Saturday morning, there was Epstein taking a seat at Cubs Convention alongside team television voice Len Kasper and inviting questions from the fans. Epstein had Hoyer, senior vice president Jason McLeod and the rest of the baseball operations team stay behind so he could face the music on his own.

"We know we fell short, and we let you guys down," Epstein said to the fans. "We let ourselves down."

This winter storm wasn't the Harper that Chicago hoped to be welcoming to town this time of year. There will be no superstar addition this offseason unless Epstein can surprisingly move a major contract like Heyward's off the books. Even the sight of a swingman pitcher like Adam Warren would've been welcomed at Cubs Convention, but the Cubs haven't even addressed their bullpen yet in free agency.

Epstein and the Cubs have doled out major contracts for Heyward, Darvish and Jon Lester in recent offseasons. In early November, they picked up Cole Hamels' $20-million option for 2019. Members of the young core have become more expensive as they've become arbitration-eligible.

The Cubs' financial limitations have become clear during this offseason in which premier talents hit free agency and the team reached a crossroads. For many fans, Harper's looming presence on the open market without interest from the Cubs is a source of frustration. 

Epstein doesn't believe the Cubs are done this offseason, though the level of addition possible remains unclear. As he often reminds, hopes for this 2019 team rest on better from the players who came up short in 2018.

Given the nature of this offseason, with the goal of a greater urgency replacing complacency, Epstein is confident in what's to come.

"We have to be excused for being excited, because we are really optimistic about this season," Epstein said. "But I completely get it from a fan standpoint. I know there are a lot of questions out there. I actually appreciate that, just to have fans who are as passionate about baseball and about winning and about the Cubs as we are. You can't take that for granted.

"It also reflects the fact that standards have been raised around here quite a bit. We're coming off a 95-win season, we've won more games than any other team the last four years and yet there are loud, legitimate questions from our fans. I think that's a good thing. I'm happy to provide answers the best I can."

Chris Emma covers the Bears, Chicago’s sports scene and more for 670TheScore.com. Follow him on Twitter @CEmma670.​​