What is Theo Epstein’s plan for the Cubs in 2020?

New Cubs manager David Ross claims this club is talented enough to win a World Series, however, the North-Siders sure don’t look like title contenders.

The Chicago Cubs haven’t done much to improve on their disappointing 2019 season that saw them finish third in the NL Central and miss the playoffs for the first time in five seasons. In less than three weeks the Cubs have their first team workout of Spring Training and they have reportedly just signed outfielder Steven Souza Jr. to their first MLB contract of the offseason.

There have been some small minor-league moves, mostly bullpen arms, but with the Cubs current financial situation, team president Theo Epstein and the front office haven’t been able to attack free agency as they have in years past.

The focus around the Cubs this offseason has been on who they were moving from their roster and less about who they were adding. With that, most people have labeled the Cubs as a team looking to re-tool. Everyone except the Cubs that is.

The Cubs’ annual fan convention took place earlier this month, allowing fans to ask decision-makers like Epstein, general manager Jed Hoyer, and rookie manager David Ross about where this team was heading in 2020. And while Epstein did tease fans a bit with the idea of the North Siders pulling a “rope-a-dope” on everyone this late in the offseason, the club president seems to be pointing towards the club standing pat for the moment.

"“Or maybe it’s going to be that type of offseason where you have to find improvement with the guys that we have. I certainly think there’s a lot of room for improvement based on certain guys being at a point in their career where they can take a big step forward. And as a team, I think coming together under Rossy’s leadership at an important time for our franchise is more than possible.”"

For a team that missed the playoffs for the first time in five seasons, and a fan base that was given a similar reason to run it back the previous offseason after an early Wild Card exit, anything but change to this roster was going to be a hard sell to Cubs fans.

However, let’s take a look at this situation from Theo Epstein’s perspective and run down a list of things that need to be fixed before being considered true title contenders once again.

His club had the third-highest payroll in baseball last season but only managed to win 84 games, despite having the projected talent of a 90-win team, according to Epstein. The Cubs have spent plenty of money in free agency in recent years, committing $207 million to Yu Darvish, Tyler Chatwood, and Craig Kimbrel alone, but the team has still underperformed since winning the World Series in 2016.

Now, Epstein needs to improve his roster while Cubs chairman Tom Ricketts and his family ownership group tighten the team’s budget after spending big in free agency as well and on adding amenities that surround Wrigley Field.

If the Cubs can’t spend money and are instead trying to cut spending, the only way for Epstein to truly improve on his roster is to move a player like Kris Bryant in hopes of an influx of prospects as well as MLB talent to plug into the roster immediately.

However, Bryant and his never-ending service-time grievance remains unresolved, which makes it hard for Epstein to move his former MVP without knowing if he’s under contract for one or two more seasons. Unable to engage in serious conversions about the team’s best asset this late into the offseason has left the Cubs with few options, none they can truly act on until a ruling is made on Bryant’s grievance case.

Once that is resolved, Epstein can either try and trade Bryant for the best package available and begin “re-tooling” or he can keep the core together at the moment and hope for better results combined with more surprises emerging like relievers Rowan Wick and Kyle Ryan did last season.

Epstein made a necessary change in letting Joe Maddon walk from the Cubs and replacing him with former Cubs catcher David Ross, who is nothing if not a positive force, sharing his optimism for this group at Cubs Convention:

"“There’s a lot of good players here, a lot of good talent here. I’m excited about the roster as it shapes up right now. There’s a lot of good, young talent. We picked up a lot of minor-league free agents. Lot of talent coming into camp as of right now, so I’m super excited about that.”"

It’s not insane to think that adding Ross and improving the Cubs; player development and scouting departments behind the scenes can bring more out of this current core of Cubs players.

The Cubs are going to head into 2020 as is, likely with an exit strategy should things fall apart. And while the Cubs brass will never come out and say it, the trade deadline could be when Bryant and others are eventually moved.

But for now, the Cubs are remaining status quo in hopes a path will present itself as the season unfolds.