Chicago Cubs: Theo Epstein faces toughest offseason yet

Chicago Cubs personnel had been promised a “reckoning” if the team failed to make the playoffs in 2019. That time has come for Theo Epstein and the team.

After a disappointing end to the 2018 season, Theo Epstein made one thing perfectly clear: 2019 would be a critical season for the Chicago Cubs – and many of the individuals employed by the organization.

Sure enough, after winning just 84 games and missing the postseason, the front office and Joe Maddon went their separate ways and former catcher David Ross is set to take his place.

The past month has also been filled with trade speculation and hypotheticals involving Chicago’s young stars. After all, Cubs president Theo Epstein has repeatedly said that there are no “untouchables” within the organization.

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Having missed the playoffs for the first time since 2014 and handing the reins to a rookie manager, the the Cubs face plenty of uncertainty heading into this winter.

What is clear, however, is that the challenge of building a winner this offseason is greater than ever for Epstein and the rest of the Cubs brass.

Competition for marquee free agents

It is easy to suggest that the Cubs should attempt to free up payroll to sign the likes of Gerrit Cole or Anthony Rendon this offseason.

The team already announced a buyout of Brandon Morrow, and they are likely to take similar steps for relievers such as Derek Holland, David Phelps and Tony Barnette. Chicago could also make room by buying out Jose Quintana, though that appears less likely.

Of course, the Cubs are going to face a ton of competition should they decide to pursue Cole, Rendon or any other big-name player.

The Los Angeles Dodgers and New York Yankees figure to throw caution to the wind. Los Angeles has spent years getting below the luxury tax, and there are reports that they could offer Rendon a lucrative, short-term deal. Meanwhile, the Yankees and Brian Cashman need starting pitching by any means necessary.

The big-market teams are hardly the only ones that will be involved. Other teams looking to make the leap and compete in 2020 – such as the Angels and Padres – are said to be potential favorites to land Cole and Stephen Strasburg (should he opt-out of his deal with the Nationals).

Plenty of teams need starting pitching.

This applies to the relief pitching market as well. The Cubs need to reload given the number of arms that they will lose to free agency or choose to buy out, but are likely to face competition from the likes of the Twins, Dodgers and Braves, amongst others. Not to mention, the median age for the bullpen arms set to hit the market is close to 35 years old.

In terms of positional players, there is a real shortage of impact players, and Epstein will face a tough decision regarding Nicholas Castellanos.

Empty promises

Theo also promised big changes after the Wild Card Game in 2018.

Yet, when the dust settled, the front office insisted on internal improvements. Epstein and his cohorts were unable to work around budget constraints and the second-highest payroll in baseball.

The Cubs may have money coming off the books, but payroll is still an issue. The Ricketts family has increased payroll in nearly every season since the rebuild began, and – despite the obvious infusion of revenue from projects in Wrigleyville – they do not seem keen on pouring too much more money into the payroll.

All of this is to say that Epstein will have to be more creative if he hopes to avoid another disappointing offseason.

The Cubs have clear and obvious needs (impact starter, late-game bullpen arms, more reliable leadoff hitter) heading into the winter. Can Theo work his magic? This will be his toughest test yet.