The Interesting Details and Complex Implications of Cubs' Upcoming Shota Imanaga Decision

[Matthew Trueblood]

The ace of the 2024 Chicago Cubs comes back for 2025 at an affordable price—but the complicated contract he signed last winter finally gets interesting this fall.

Image courtesy of © Rick Scuteri-Imagn Images

Remember, though it's nominally worth $53 million over four years, Shota Imanaga's deal has a huge wrinkle in it. Imanaga made $10 million ($9 million in base salary, plus a $1-million signing bonus) in his first year Stateside, and will make $13 million this year. So far, so simple. After this season, though, the Cubs have to elect to exercise or decline a $57-million option covering 2026-28. If Imanaga's second season is anything like his first, of course, they'll exercise it. Should he regress heavily or get badly hurt, though, they might decline it—in which case, Imanaga would have the right to exercise or decline a $15-million option of his own for 2026.

If all that happens (Cubs decline, Imanaga exercises for 2026), the Cubs would have a two-year, $42-million option for 2027-28, on which to decide at the end of 2026. For those whose head is starting to swim, yes, that $15 million and $42 million would add right back up to $57 million. The catch is, if the Cubs exercise their three-year option this fall, the money would be spread thusly:

• 2026: $20 million
• 2027: $20 million
• 2028: $17 million

On the other hand, if the team declines, Imanaga uses his player option, and they then want to retain him for the final two years of the deal, it would be structured:

• 2026: $15 million
• 2027: $24 million
• 2028: $18 million

By the way, too: if the Cubs turn down that two-year option at the end of 2026, Imanaga can still secure for himself a final $15 million on a player option for 2027. So, effectively, the team has an opt-out decision to negotiate each of the next two years with one of their best pitchers. That's fine; the deal is structured to give them flexibility.

However, it's also structured to encourage them to play chicken with him. Each time they have a club option, they stand to save a hefty amount ($5 million in 2026; $9 million in 2027) if they turn down their side and he exercises his. Of course, in most cases, them turning down their option and him exercising his would mean that things are going badly for him, but imagine this scenario:

1. Imanaga has a solid but unspectacular second season in Chicago. The Cubs, noting his age, lack of velocity, and injury risk, decline their three-year option.
2. However, Imanaga (seeing more upside for himself than $30 million over two years and not trusting the Cubs to pick up their two-year option after they just declined a similar one) declines his player option, becoming a free agent.
3. Surprise! The Cubs spring their trap, and extend Imanaga a qualifying offer. He's eligible to receive one, and while the offer is likely to be right around $22 million this fall, the Cubs could feel that to be a better bet for them than committing $57 million over three years, even if it means they pay a little more in the one year they would have him.

Because of that very risk, it's unlikely that Imanaga will opt out. If the Cubs turn down a chance to keep him for $57 million over three years and then they can attach the qualifying offer to him and dampen his market even further, it's hard to see how he could make more by declining the offer. So, he'd effectively be choosing $22 million (or so) on a one-year deal over $30 million over two years, with the chance to get another $27 million and lose just one more year in the second scenario. 

Thus, if the Cubs want or need to create some extra payroll flexibility for 2026, they might well turn down their option on Imanaga, even if they want to keep him—and perhaps even if they want to keep him for the long haul. While I firmly believe that the risk of lost games in 2027 is being overstated by much of the industry, that risk hangs over the year of Imanaga's deal in which he would make by far the most money, should the Cubs decline their first option and pick up their second. If it gets that far, it's almost as hard to imagine Imanaga declining his second player option as it is to see him declining his first, because being a free agent in the offseason of 2026-27 is not likely to be much fun.

Some of the intrigue here comes not just from Imanaga's deal itself, but the context in which it exists. Justin Steele is under team control through 2027, but he's going to be very expensive in 2026 and 2027. Obviously, a passel of newcomers to the team become free agents after 2025, headlined by Kyle Tucker and Ryan Pressly. Jameson Taillon, Ian Happ, Nico Hoerner, Matthew Boyd, and Seiya Suzuki all hit free agency after 2026 (if none are traded sooner). The various possible forms this contract could take might each be the best one for the Cubs in different circumstances, based not just on his performance but on the success of the 2025 team; the development of key prospects, both on the pitching front (can Cade Horton, Ben Brown or Brandon Birdsell claim a long-term rotation spot next year) and on the positional side (do Michael Busch and Pete Crow-Armstrong need replacing? Alternatively, are they in line for big extensions?); and on the health and play of Taillon, Steele, and Boyd.

Another very good season from Imanaga could obviate this discussion. A flat $57-million commitment coming off a second campaign wherein he was 10-15 runs better than an average starter would be a no-brainer, especially because it would be priced for CBT purposes not at $19 million but (since it's attached to his 2024 and 2025 salaries, all part of one deal) at $16 million. If he struggles at all or deals with arm trouble, though, things will get very interesting—and already, the unique shape of this deal has had some influence over the progress of building the rest of the roster.

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