Presented By Cubs Insiders

SAN DIEGO — In recent weeks, the expectations surrounding the Cubs offseason have crescendoed to the point where the question is not if they're going to trade a core player, but when

The writing has been on the wall teasing a major move, both from the Cubs themselves and from word around baseball published in national and local reports.

Following a disappointing 84-win season that somehow ended in a fashion that made the tail end of 2018 look like a smashing success in comparison, Theo Epstein called for change in every corner of the organization. That's manifested itself in a new manager, a new coaching staff, a complete restructuring of the player development and scouting departments and even a shakeup on the training staff. 

But as of yet, the roster remains unchanged — apart from the handful of players that hit free agency after the World Series ended. 

A team's 25-man (now 26-man) roster is constantly evolving, but if the Cubs return largely the same team that crumbled down the stretch last year, how can that bring about the change they desire? Then again, what's the point in making a move just to make a move?

"We're not gonna force anything," Epstein said Monday on the first day of MLB's Winter Meetings. "We're not gonna make change just for change's sake. I do think we can benefit from some change in certain areas and we are interested in pursuing some opportunities — opportunities to get better immediately and opportunities to make our future healthier as well. 


"But you can't force anything. You have to be realistic about the market that you're in and what opportunities come, but there are a lot of promising leads out there. Obviously we haven't gotten anything to the point of consummating a deal yet, but we're at the early stages of the offseason for us at this point, still."

In other words, the Cubs aren't going to sell off Kris Bryant or Willson Contreras or anybody else just to shake up the roster. They're only going to do it if some other team meets their asking price or returns fair value for the player they'd be trading away. 

That being said, the Cubs probably could use a shakeup to their core of players. Maybe "complacent" is too strong of a word to use regarding how the team has struggled to reproduce 2016's epic World Series run, but it also might be the best word to sum up the "winner's trap" Epstein detailed the day after the season ended

Everybody knew the bill would come due for the Cubs like this eventually. That's what happens when you have a wave of prospects all make their big-league debut around the same period of time — they all run out of club control at the same time. Coupled with the looming expiration of Anthony Rizzo's team-friendly contract and the tail end of the Jon Lester and Jose Quintana deals and the window is closing on the Cubs. 

If the last couple seasons had gone differently, maybe there would be an easier case to be made that the Cubs shouldn't be thinking about selling off parts and changing the roster and instead, adding to the group and going all-in for another couple championship runs before the window of contention runs out.

But watching the way the last two Septembers have unfolded and examining how the Cubs have fallen short of expectations each season, it's been apparent something had to be done differently. Epstein's front office can no longer simply expect the talent they have on the roster to carry the team into another National League Championship Series or beyond.

That's why they're focused this winter on not only improving the wins column for the 2020 team, but also looking at the bigger picture. They are not going to mortgage the future to go all-in on only the next two seasons.

That makes for a tricky and complicated offseason. It's hard to envision the Cubs being a better team in 2020 if they get rid of players like Bryant or Contreras. But it's also become clear that they're not just an addition or two away from being a legitimate World Series contender, so they need to focus more long-term.

"It's often the case where you're trying to serve multiple masters," Epstein said. "Or you have to manage different parts of the roster, manage different windows, different periods of time, try to build health in the organization, put an emphasis on young players while simultaneously polish the major-league roster. It's not that uncommon. 


"We knew this day was coming where we'd be reaching a period where we had just a couple years left of control on a lot of really good players and there were always gonna be challenging decisions that came along with it. We're just getting closer to that period of time. But it's something we've all been thinking about for a long period of time. It's not sneaking up on anybody."

When the MLB Winter Meetings were last in San Diego, the Cubs made waves by adding Joe Maddon as the manager and Jon Lester as the big-name free agent. With Bryant and a slew of elite prospects exploding onto the scene in their first big-league seasons, the talk around this franchise started including a word that is not thrown around lightly in sports. 

Fast forward five years and the Cubs are clearly not in the midst of a dynasty. Four straight trips to the playoffs, three straight trips to the NLCS and a World Series ring are nothing to sneeze at, but all those accomplishments are going on three or four seasons old at this point. 

The new world order in Cubdom is trying to serve those two masters Epstein spoke about — competing in a wide-open division in 2020 while also ensuring the longer-term health of the franchise is in a better spot than it currently sits.