Chicago Cubs: Which first time manager will have the most success?

Chicago Cubs: David Ross

The last time we saw David Ross on a baseball diamond, he was hitting a home run in Game 7 of the 2016 World Series in Cleveland. Just three years later, he now becomes the skipper of the team that he already, in a big way, was a leader for in 2015 and 2016. Ross was primarily being groomed for this job when he served as a backup catcher on those two great Chicago Cubs teams.

Cubbies Crib has, of course, spent a lot of time this offseason analyzing the Cubs’ chances for 2020 and what they need to do to continue to contend. After four straight seasons of at least 92 wins and making the playoffs, the team won just 84 in 2019 and missed the postseason tournament. Ross has been brought in to try to keep this team’s contending window alive.

The expectations for the Cubs in 2020 depend a lot on what direction the front office decides to go this offseason, and we’re all still a little unsure of what that will be. Trade rumors have swirled around the likes of Kris Bryant, Willson Contreras, and Kyle Schwarber. How many of them will be back next year? How will the team try to upgrade without spending a lot of money?

No matter who is on the roster next year, the front office believes that Ross can hold players accountable – including ones he played alongside just a few years ago. It appears that that was lacking a little towards the end under Joe Maddon. The team should still be able to contend in 2020, though the front office will have to get creative this offseason to set the team up well for long-term success under Ross.