Chicago Cubs: Theo Epstein seeks change – can he find the right guy?

With the season complete and Joe Maddon’s office at Wrigley Field vacated, the pressure is on Theo Epstein to find the right guy to lead the Chicago Cubs.

After five years, four postseason berths, a pair of division titles and a World Series title, the Joe Maddon era has come to a close. For the first time in years, the Chicago Cubs won’t play baseball in October – and all eyes will be on president of baseball operations Theo Epstein in what might be the most critical offseason of his Cubs tenure.

Alongside Maddon, Epstein spoke to reporters prior to the team’s season-ending loss in St. Louis, offering praise for the 65-year-old three-time Manager of the Year and framing the decision as amicable and mutual.

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"“Sometimes it’s just time,” Epstein told The Athletic (subscription required). “It’s time for change. We’re going to go through some transitions in various levels of the organization. I think change will be good for the group and allow them to keep growing.”"

Since Maddon led the Cubs to the historic World Series title back in 2016, many have claimed the team played without a sense of urgency. In 2017, the blame fell on a ‘World Series hangover’ – which Chicago overcame to advance to a third-consecutive NLCS. Last season, Epstein pointed to a ‘broken offense’ that fell flat – ending the team’s season at home in the National League Wild Card game.

This time around, a historic collapse in the season’s final weeks, where the club dropped nine of 10 closed the book on the team’s postseason hopes – and Maddon’s tenure on the North Side. He’ll look for his next opportunity after winning 471 regular season games – with plenty of clubs entering the offseason with managerial vacancies.

San Diego, San Francisco and Pittsburgh have clear openings – and several other guys, including the Angels’ Brad Ausmus and Mets’ Mickey Callaway, could be on the hot seat, as well. Time will tell how Maddon’s future plays out – but don’t expect him to be a free agent for very long this winter.

After an 84-win 2019 season – one that fell well short of any and all expectations in Wrigleyville – Epstein knows that drastic change is needed. Maddon is just the first of what I expect will be many moves as the Cubs look to retool and get back to October in 2020.

"“It’s just about looking forward to the next five years,” Epstein said. “Like Joe said, sometimes it’s just time. We’re in transition at different levels of the organization. Sometimes you’re left with a choice between status quo or change and you feel like change is necessary. This status quo was a great status quo. It’s status quo with a Hall of Fame manager. Sometimes change can still beckon. And that’s where we are.”"

It’s too soon to tell who will get the call from Epstein. Former Cubs catcher and fan favorite David Ross has expressed his interest in the role. Bench coach Mark Loretta makes a good amount of sense, as well. The list goes on and on from there – but expect a thorough, detailed search this winter. Because the truth is simple: Epstein cannot miss on this move.

Maddon may be on his way out after the team underperformed in 2019. But Epstein is far from blameless in this whole thing after missing on several key free agent signings in recent years. Paired with spending limits from ownership, there’s plenty of blame to go around. In the upcoming managerial search, though, there’s one man to shoulder the responsibility: Theo Epstein.