“It was really nice to be able to play five home playoff games…. I wish we could’ve played a lot more,” Jed Hoyer said after the Cubs lost their NL division series to the Brewers on October 12. But that hope can hardly become a reality without rebuilding an entire bullpen from scratch. Most of the team’s vital relievers from this past season are either free agents or gone.

On Tuesday, Jed Hoyer’s team announced it had traded Andrew Kittredge to the Orioles for cash considerations. On August 6, 2025, Kittredge threw an immaculate inning against the Reds, striking out all three batters, and that too using only nine pitches. This was the sixth immaculate inning (striking out all 3 in one inning) in the history of the team.

Last offseason, the veteran engaged with the Orioles on a one-year deal, $10M. Kittredge earned $9M this season, then had $9M team option for the next season (2026), along with a $1M buyout.

Now, for Jed Hoyer, the pressure to bounce back in 2026 is getting more intense. The Athletic pointed out, “That move, along with the impending free agency of Brad Keller, Drew Pomeranz, and Caleb Thielbar, could mean that the Cubs are entering a winter in which they will have to replace almost every key contributor to the bullpen.” However, will the Cubs spend freely this time to become a strong contender?

As per Sahadev Sharma of The Athletic, “….league sources told The Athletic not to expect the Cubs to jump in on big-name free agent relievers, at least not early on. The Cubs are not going to be setting the market on relievers… Perhaps someone could fall through the cracks and be available in January or February at a deal that could provide potential surplus value. In that case, the Cubs may pounce; otherwise, reeling in big fish in the reliever department in free agency just isn’t in the cards for this front office.” 

Vital stars like Edwin Díaz, Devin Williams, and Robert Suarez will be available. However, with Edwin Díaz and most probably Robert Suarez going to sign a deal with an AVV of a minimum of $20M, the Cubs may not go for them.

A more probable scenario could be a trade just like the one the Astros made last season when Jed Hoyer’s team got Ryan Pressly. But that trade was not successful, either. Pressly struggled since joining the Cubs. In 19 appearances, he lost his control and posted as many walks (9) as strikeouts (9). The star’s 4.52 FIP was also worse compared to a 5.71 ERA.

Sharma talked about stars like Luke Little and Jack Neely, and the forgotten Eli Morgan, affirming that most of these moves will be non-costly veterans and some unknown stars. They are all either struggling with injuries or spending their time in rehab assignments.

And this approach somehow worked this season. The Cubs ended up with a powerful bullpen as the season went on.

So, Jed Hoyer could think that there is no need to change things up. But fans are hoping that the team will spend money and make a powerful bullpen, and go deeper in the postseason run beyond the Divisional Series.

The bullpen has already taken a bitter pill with Andrew Kittredge’s exit, and now the rotation picture looks even murkier after a left-handed pitcher’s free agency decision. With several contracts expiring and the top management balancing payroll flexibility, Chicago has no room for errors.

Imanaga’s gamble signals a mutual break for flexibility

According to Jay Cohen of FOX 32 Chicago, Shota Imanaga and the Chicago Cubs both declined to exercise their respective contract options.

The Cubs opted against guaranteeing $57 million for the 2026-28 seasons. And Imanaga vetoed a $15.25 million player option for 2026. That led him to enter free agency, though Chicago could still extend a qualifying offer of nearly $22 million for 2026.

The 32-year-old Shota’s decision comes after receiving $23.25 million over two MLB seasons, underlining an All-Star 2024 campaign where he went 15-3 with a 2.91 ERA and finished fourth in NL Rookie of the Year voting. However, his 2025 stats declined slightly, a 9-8 with a 3.73 ERA and a hamstring strain sidelining him for a full month. But his consistency makes him a top left-hander in the market. 

For Hoyer, losing him without a qualifying offer or replacement plan could only deepen the rotation void, particularly when rivals will also be eyeing pitching reinforcements.

Jed Hoyer’s offseason decisions will determine the Cubs’ fate in 2026, as pressure is building to stay competitive in the market.