This story was excerpted from Jordan Bastian’s Cubs Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

CHICAGO -- This is going to be a critical offseason for the Cubs. The two-year rebuild is in the rear-view mirror, and this past season raised expectations on the North Side to the point that September’s fade felt excruciating for a fanbase craving October baseball again.

The task ahead for president of baseball operations Jed Hoyer and general manager Carter Hawkins is to ensure that the positives outweigh the late-season negatives, and that 2023 can eventually be viewed as a true stepping-stone year. And they fully expect shortstop Dansby Swanson to be involved in the planning.

“Carter and I offered him an office,” Hoyer quipped at the end of the season. “I told him he had to wear khakis. He said that was a deal breaker.”

All jokes aside, Swanson does indeed intend on having his voice heard in the coming months as the Cubs plot their course for ‘24 and beyond.

When the shortstop signed his seven-year, $177 million pact with the ballclub last winter, he did so hoping to quickly help transform the North Siders back into annual postseason participants and World Series contenders. It is why he was vocal with Hoyer ahead of the Trade Deadline, doing what he could to convince the front office to push thoughts of a sell-off to the side.

Now, the Cubs have a chance to be aggressive in the winter ahead, building on a group that was one of baseball’s best teams in the season’s middle months. The final three weeks went in the opposite direction, leaving Chicago stranded on the playoff’s doorstep. A playoff berth will be expected in ‘24 for an organization with a solid foundation in the big leagues and one of baseball’s top farm systems.

“I'm sure we'll have some conversations,” Swanson said after the Cubs’ final game of the season. “If anybody knows me, I'm pretty open with my opinions when it comes to stuff like that. So I'm sure we'll have plenty of conversations over the next however long, about it all.

“We obviously know that we fell short this year, and that there's plenty of work to be done to get to where we want to get to. And I'm sure we all kind of have our own opinions on what that's going to take. And it's just a matter of all that stuff coming true.

“So, yeah, I'm sure that this offseason will be filled with plenty of just honest conversations about what we can do better -- whether that's players, philosophy, you name it.”

Hoyer said he loves that aspect of Swanson’s personality and leadership.

“We've talked about him being a winner,” Hoyer said. “And I know he's going to be in our ear playing assistant GM, but I like that partnership. He just wants to win and he's going to throw ideas that he believes will add to winning.

“And we'll probably take some and listen to him and, some others, we may not. But we do like that partnership. And it's great that his heart's always in the right place.”