For a Chicago Cubs team that hadn’t seen playoff baseball for five years, hadn’t played a postseason game in front of fans since 2018 and was eight years removed from a playoff victory, there is plenty to be happy about after this season. The Cubs won a playoff round and fought back from down 2-0 in the NLDS to take the Milwaukee Brewers to the brink. But ultimately, when the season ends in a loss, disappointment lingers.

Primarily, it is the clearest sign that more work needs to be done. Team president Jed Hoyer and his front office are well aware of that. There are people in the organization who were already getting a jump on things, digging in on minor-league free agents and under-the-radar targets while the playoffs were in full swing. Now everyone’s focus can be solely on how to improve the roster heading into the winter.

Here are three big questions facing the Cubs.

What does the future hold for Kyle Tucker?

It’s the question that’s been asked since the Cubs acquired Tucker in a blockbuster offseason trade last year. What the Cubs parted with — Isaac Paredes, Cam Smith and Hayden Wesneski — has the potential to be viewed as quite a haul for the Houston Astros. But the Cubs were at a point in time where winning was paramount and Tucker was supposed to take the team to another level offensively.

For a time, that appeared to be the case. With Tucker, the Cubs’ offense was one of the best in baseball during the season’s first half. But a second-half marred by injuries and ineffectiveness has taken the shine off Tucker marriage to the Cubs. Re-signing Tucker is a long shot.

How much Tucker would make is a big question. The Cubs seem disinclined to push things into the $300 million or above range. In fact, they would probably be hesitant about anything long-term at a high rate. And if Tucker is looking for a pillow contract to build up his value, which there’s been no indication of, why would he want to come back to Wrigley, where the wind plays havoc on left-handed power hitters? Cody Bellinger will likely cash in after a season at Yankee Stadium, where lefties thrive.

If Tucker doesn’t come back, how the Cubs react will be key. Do they go young on offense and shift their resources to other areas? Do they sign a stopgap veteran as Owen Caissie, Moisés Ballesteros or Kevin Alcántara get acclimated to the highest level? Maybe they try for a reunion with Kyle Schwarber or make another run at Alex Bregman? The answers to those questions will be clearer after Jed Hoyer talks this week and then more so next month at the GM meetings and as the offseason progresses.

What will the starting rotation look like?

Once thought to be a layup, picking up Shota Imanaga’s complicated option may not be so easy. His performance down the stretch and in the playoffs certainly brought up many questions that didn’t seem to exist before.

Whatever happens there, the Cubs believe this is the area where they can improve the most. In an ideal world, they add more swing-and-miss to the rotation. But that’s easier said than done. Everyone wants strikeouts, so they cost more money to acquire.

But perhaps the Cubs revisit some trade talks that stalled over the summer — Joe Ryan would sure look good leading this rotation with an elite defense behind him. Free agency isn’t littered with impact arms, but there are some intriguing starters, led by Framber Valdez and Dylan Cease. Chicago could head back into the Japanese market, where Tatsuya Imai could be posted and receive a big payday.

But the Cubs have tended to shop more in the middle market for free agents. If there’s a short-term deal to be had with upside, they’ll be interested. The Matthew Boyd deal certainly turned out well.

With a healthy Cade Horton looking to take another step forward and Justin Steele likely good to go at some point in the first half, the rotation should actually be in better shape. Boyd and Jameson Tailon are both under contract for another season. The Cubs will discuss picking up Colin Rea’s $6 million option (with a $750,000 buyout).

How will the Cubs go about rebuilding their bullpen?

The Cubs built a really strong bullpen without spending big, a credit to the front office and the pitching coaches. But they may have to do it once again, considering the potential losses. Brad Keller, Drew Pomeranz and Caleb Thielbar are all soon-to-be free agents, and Andrew Kittredge has a $9 million option with a $1 million buyout.

Keller indicated he’d love to come back and Pomeranz suggested he wasn’t ready to retire. But this is not the type of organization that pays big for relievers after a great season. Like they did with this quartet, they’d rather find them before the bounce back or breakout occurs. But ruling any of them out just yet would be premature.

For now, this is a group that’s looking like it will need to be rebuilt. The only veteran under contract is Eli Morgan, who missed most of the season with an injury. Daniel Palencia will return and the hope has to be that this was a true breakout. Porter Hodge’s struggles in 2025 show that it can’t be assumed. Other than that, one has to wonder if Ben Brown will make the permanent conversion to relief and if any other young arms emerge over the winter and spring.

That the Cubs nearly went out of their comfort zone for Tanner Scott and were seemingly saved by the always aggressive Los Angeles Dodgers means it can’t be ruled out that they will love a big-name free agent and choose to spend on a reliever. But it’s not their standard practice. Expect more bargain shopping that leads to grumbling by some, but has been proven to be effective.