Jed Hoyer won’t get much time to settle into his new job as Cubs president of baseball operations.

This is a pivotal winter for the future of the franchise. 

For starters, the “Core 4” are all nearing free agency. Anthony Rizzo, Kris Bryant, Javy Báez and Kyle Schwarber are under team control for only one more season and Willson Contreras is set to hit the open market in two years. The window of contention with this group is closing.

Hoyer said the front office does not have any ongoing extension talks with players right now, but expects those to pick up later this offseason. 

Then there are the bigger picture challenges facing the organization. 

This team has spent all but four days in the playoff hunt over the last six seasons, but they’ve also fallen short of their own expectations the last few Octobers and want to shake up the roster in some way this offseason.

There are still a lot of talented players and they’re led by David Ross, who just finished as a Manager of the Year finalist in his first season on the top step of the dugout. 

The building blocks are clearly there for the Cubs to go all-in for another World Series title in 2021. But they also want to prioritize the long-term future of the organization, especially with the potential of so many key players leaving town within the next couple years.

It’s possible to do both at the same time. That’s where Theo Epstein’s “thread the needle” comment comes into play. 

The challenge is figuring out how to do that.

“We have a great team; we have a team that won the division last year,” Hoyer said. “Obviously the playoffs have not gone as we hoped in two of the last three years. But ultimately the goal every year is to give ourselves a chance and that’s not gonna change. 

“In this job, you always have one eye on the present and one eye on the future. The truth is that given the service time realities, that eye might be a little bit more focused towards the future than usual. But that doesn’t take away from the goal, which is always to make the playoffs and give this organization a chance to go deep in October.”

Hoyer pointed to recent history — the 2016 Cubs, 2020 Dodgers and 2018 Red Sox — to show how the best team in baseball sometimes hoists the World Series trophy at the end of the year. 

But that’s not always the case. Much of the time, it’s simply about who gets hot at the right time and sustains that run throughout October — like the 2019 Nationals.

Since Hoyer and Epstein took over the Cubs front office nine years ago, they set their goal of sustaining success for this team from season to season. They knew that the more chances a team has at the playoffs, the more likely it is everything will fall in their favor.

The Cubs could certainly go the route of a full-on teardown and trade away most of their short-term assets in an attempt to build a new core to make another run at a title. 

But it’s more realistic that they try to balance both — winning in 2021 while also exchanging some short-term assets for long-term resources (either via extensions or trades).

“Given our resources and given our talent level, I think we should field a team that’s playoff-worthy every single year,” Hoyer said. “I think we can do that and have a team that’s positioned long-term as well.”

So expect some change to the Cubs roster this winter, potentially even some major change.

But with the NL Central wide open, the Cubs are once again setting their sights on competing for the division in 2021.

“One of my favorite aspects of this job is there’s always a new and different challenge,” Hoyer said. “The players change, the financial realities change, the rules of the game change, team-building strategies change. We faced a fascinating challenge when we got here nine years ago. Then, after building up the farm system, we faced another challenge to go from rebuilding to contention. 

“And now we face a new challenge imposed by the reality of our player service time and the realities of our world in 2020. As with all the challenges we have faced here, we will study them, we will use our collective experience and then we will move boldly to do what is in best interest of the franchise.”