CHICAGO -- There is no escaping the reality that the Cubs are approaching a transitional phase in the franchise timeline. That is why a cloud of urgency has hovered over a core group that again fell short of rekindling past October magic.

The Cubs are not only entering a critical offseason for evaluating that core and how it fits within the future plans, but president of baseball operations Theo Epstein is approaching his own free agency after 2021. In his annual season-ending gather with reporters on Monday, Epstein expressed his intention to stay focused on the Cubs through next season.

"My expectation is that I'll be here," Epstein said. "My expectation also is that I'm going to do whatever is best for the Cubs every day. And that means being thoughtful about a transition, whenever that may come. I'm focused on on the 2021 Cubs and how to position ourselves for long-term success."

That means Epstein will balance potential change on two fronts. There could be alterations this winter to a core that has not been able to deliver October success over the past four years. Beyond that, Epstein will weigh how he factors into the picture beyond the 2021 campaign.

As he does at the outset of each offseason, Epstein will soon meet with Cubs chairman Tom Ricketts to discuss the direction of the franchise. That will surely include discussing whether the organization is facing a future without Epstein starting in 2022, and if that means general manager Jed Hoyer is next in line for the top front-office job.

At this point, much of this situation exists in the realm of speculation, but Epstein did offer a strong backing of Hoyer on Monday.

"Jed is someone who's been a huge part of the success here," Epstein said. "He's also someone who's already been a successful No. 1 in baseball operations when he served as the general manager of the Padres. I recognize all those qualities and everything that he brings to the table, and how much he's done for for this organization.

"Tom and the Ricketts family do, too. So that's obviously a factor when when you start to set out and discuss what a transition might look like."

Epstein has been on record throughout his career about being a believer in legendary football coach Bill Walsh's thoughts on a leadership timeline. The theory is that 10 years is a good time frame for a coach or executive to stay in one place before moving to the next challenge.

Epstein was the GM of the Red Sox from 2003-11 before coming to Chicago to take the president of baseball operations post with the Cubs. He later signed a five-year extension that ran through the '21 season, which would be his 10th at the helm for the North Siders.

During Monday's conversation, Epstein was asked if he would want to discuss another extension with the Cubs.

"I've been pretty transparent," Epstein said. "I think there's benefits to change after a significant amount of time on the job -- about a decade. And I think I have to keep that in mind without making any definitive statements. We will be definitive. We will have a transition plan. We will have a structure moving forward.

"We just we can't share that with you guys. We haven't gone through that process. And we're going to. We're going to do what's in the best interest for the Cubs. But, I have to be honest with myself, my own values, beliefs, strengths, limitations, and recognize that as I look at what is best for the Cubs."

Epstein, Hoyer and the front-office group will also have to take a hard look at the roster while planning for 2021 and beyond.

Key pieces Javier Báez, Kris Bryant and Kyle Schwarber are only under club control through the 2021 season. Anthony Rizzo would join them if the Cubs pick up his $16.5 million team option, as expected. Willson Contreras is among the players under control through '22.

With the caveat that the 60-game season came with a unique set of challenges, that core offensive group of Báez, Bryant, Rizzo and Schwarber underperformed this year. The lineup as a whole was a weakness and the Cubs managed just one run in the two-game sweep at the hands of the Marlins in the Wild Card Series at Wrigley Field.

While it would be easy to cite all the challenges of the 2020 campaign -- with many being justified -- Chicago's offense has had similar flaws in each of the past few seasons. Many of the old issues were still present this year, and the meager output in October is part of a larger problem (10 total runs in the past eight playoff games, dating back to 2017).

"We have not performed up to our expectations offensively," Epstein said, "and especially at the most important times of year. And sort of simply hoping for a better outcome moving forward doesn't seem like a thoughtful approach. So, embracing some change, even significant changes, is warranted."

As for the Cubs' payroll for next season, Epstein said, "The only thing I can I can acknowledge is that we're in a period of great uncertainty."

Right now, Major League Baseball is holding the postseason in bubble sites due to the ongoing COVID-19 pandemic. Trying to predict what the 2021 season will look like is impossible at the moment. That creates a challenge for all 30 teams, who are dealing with unknowns about roster structure, playoff format, rules and revenues.

"We need to be versatile," Epstein said. "We need we need to be adjustable and we need to be effective, despite the uncertainty [of] the landscape."

That will include being open-minded about changes to a core that captured a World Series title, three division crowns and five playoff berths in six years for a franchise that had been long-starved of championships.

"Is it an end? No," Epstein said. "Is it a bit of a crossroads and clearly a period of transition? Yes."