Chicago Cubs could lose half their team this offseason: Who will stay, who will go

Shota Imanaga has a uniquely structured contract that offers the Cubs the choice to exercise a three-year, $57 million extension after 2025. If the Cubs decline that option, Imanaga will have a $15 million player option for 2026.

Despite his postseason struggles, the Japanese southpaw is a valuable asset. He’s also a relative steal when it comes to front-three starting pitchers at $19 million per season over the next three years. Expect the Cubs to exercise their option.

Swing man Colin Rea is also a steal for the Cubs at $6 million. They’ll also likely pick up his option.

Don’t expect them back

The loss of Kyle Tucker will hurt the most this offseason. While there’s a slight possibility of the Cubs reversing course and opening up their wallets for the four-time All-Star, nobody should count on it. It’s especially far-fetched to imagine a scenario where the frugal Cubs ownership outbids the Yankees, Dodgers, Red Sox, and Phillies to secure Tucker for the next decade or so.

Bullpen saviors Brad Keller, Drew Pomeranz, and Caleb Thielbar came from varying points of career near-ruin to make up the nucleus of a surprisingly good bullpen. All have earned the right to be welcomed back in 2026. History tells us, though, that the Cubs do not dish out big money to relievers coming off one big season.

Manager Craig Counsell had championed Keller’s cause to be brought on to the team last offseason. So, that might make the right-hander the most likely of the three top relievers to be brought back.

Justin Turner’s experience and clubhouse leadership made him a valuable asset this season. But it makes no practical sense to have a part-time, defensively subpar 41-year-old first baseman/DH taking up a roster spot. Turner’s $10 million mutual option will likely be declined by the Cubs. Instead, they may opt for the $2 million buyout and, possibly, offer him a coaching position.

Aaron Civale finds himself in the same situation as Keller, Pomeranz, and Thielbar, only without the significant Cubs body of work behind him. There’s definitely value to having a swing man like Civale on the Cubs, it’s just that other teams will likely pay more for his services.

Could trade deadline acquisition Michael Soroka be signed on a one-year deal in hopes of a turnaround and a return to free agency in 2027? Possibly. The Cubs are specialists in pitcher rehabilitation, so he’d sure have the right team for a career rebirth.

Gone

Andrew Kittredge worked his way into Counsell’s circle of trust after coming over from the Orioles at the trade deadline. The problem is with his $9 million club option as a 35-year-old middle reliever. That will be too rich for the Cubs’ tastes. If Kittredge hits the open market and is forced to lower his asking price, there would be a very remote possibility of a Cubs return.

Willi Castro can play every position except catcher and pitcher. That, alone, makes him valuable. He could also hit a bit– just not on the Cubs. It would be nice to have him back. However, he’ll make more on the open market than what the Cubs would feel comfortable paying him.

Carlos Santana was brought aboard late in the season as a defensively-sound veteran first baseman to aid Michael Busch. As things turned out, Busch didn’t need any aid and the Cubs didn’t need another 40-year-old backup first baseman. Santana will be allowed to move on.

Taylor Rogers and Ryan Brasier just never achieved any level of sustained success in the Cubs bullpen. The latter was hampered by injury and the former riddled with inconsistency.