Chicago Cubs: Without change, how can this team succeed this season?

This week, Theo Epstein and David Ross insisted they intend to win this season, despite seeing the Cubs roster take steps in the wrong direction this winter.

Change is afoot. A reckoning is coming. This is the sentiment we’ve entered each of the previous two offseasons as Cubs fans. Last winter, an ill-fated signing of Daniel Descalso highlighted months of inactivity by Theo Epstein and the front office. This year, it’s been a hodgepodge of minor league deals with just two big league signings – neither of whom are difference-makers.

Despite all this, Epstein and his first-year skipper David Ross still believe they have a winning ball club. That may very well be true. After all, the team boasts some strong individual talents in Javier Baez, Willson Contreras, Anthony Rizzo and Kris Bryant. But there are more question marks than the front office would like to admit – namely on the pitching staff and the bench.

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The entire seasons seems to be riding on Ross changing a culture that seemingly grew too lax in recent years under former manager Joe Maddon, who took some parting shots at Epstein while speaking with ESPN on Monday.

"“The key is preserve all the things that we’ve done well,” Epstein said. “But, add new elements, new standards and I think this new environment will help our guys get more out of themselves and will help us as a team certainly outperform where we ended up last year.”"

All offseason, Epstein has shopped his two-time All-Star backstop and a former MVP in Bryant. But his unresolved service time grievance that stretched into the offseason’s final weeks lended too much uncertainty and, at least to this point, scrapped any trade.

The team added potential arms en masse, opting to go with quantity over proven quality with the offseason signings. Sure, some of those guys could work out this season – in fact, they have to if Chicago has any plans of contending in an increasingly competitive division. Epstein’s job may be riding on the outcome of this season – but only time will tell.

"“I’ll be honest, it hasn’t been as much turnover as we expected,” Epstein said. “All along, we weren’t going to force change. We were seeking it in certain areas and seeking improvement in certain areas, but I feel like any time you go out there saying, ‘We need to accomplish change just for change’s sake,’ you probably make bad deals and you make a tricky situation worse.”"

Now, Epstein cannot and should not trade guys of the caliber of Bryant or Contreras simply to say they did so. But standing pat in a mess of their own making isn’t exactly a desirable course of action, either. Chicago has a lot of money coming off the books after the 2020 season – which should hopefully allow the front office to make impactful moves moving forward.

But for now, they’re betting on Ross’ ability to command the clubhouse and alter the culture at the Friendly Confines. The front office has put him in between a rock and a hard place – it’s on the former fan favorite catcher to make the best of the situation and try to lead the Cubs to the postseason.