The Cubs Missed Out on Tatsuya Imai: Why the Deal Fell Through and What It Means for Chicago’s Offseason Strategy

All offseason, it seemed like the Chicago Cubs were poised to make a significant splash in the free-agent market by signing Japanese right-hander Tatsuya Imai. Many industry insiders were predicting that the Cubs were the favorites to land the highly sought-after pitcher, and there was a palpable sense of anticipation that the deal would soon be finalized.

However, the unexpected happened — the Houston Astros swooped in and secured Imai’s services instead. The Astros signed the right-hander to a three-year, $63 million contract with opt-outs after the 2026 and 2027 seasons, a deal that surprised many given the Cubs’ previous involvement.

It raised some eyebrows that the Cubs, who were widely believed to be the front-runners, didn’t end up landing Imai, especially considering the relatively modest contract that was ultimately offered to the pitcher. Chicago’s front office, which is known for its cautious approach to big-money deals, would have seemingly been willing to meet Imai’s asking price — so what went wrong?

The Cubs’ Near-Miss with Imai: What Happened?

As the offseason went on, it became clearer that the Cubs were very much in the running to land Imai. The pitcher was one of the most highly touted international free agents, and many expected the Cubs to strike early in a bid to solidify their rotation.

However, the deal never came to fruition, and it turns out that the crux of the situation rested on one key factor: the contract’s terms, specifically the inclusion of an opt-out clause after the 2026 season.

According to an insightful report from North Side Baseball, the Cubs were reportedly on the verge of finalizing a deal with Imai before super-agent Scott Boras played his final card. Boras, known for his aggressive contract negotiations, reportedly leveraged the Cubs’ final offer to secure a better deal from Houston, which included the opt-out clause.

Matthew Trueblood, writing for North Side Baseball, explained the situation: “Cubs thought they had a deal all but complete with Imai, only to have Boras leverage their last offer into one from Houston that included one of the key provisions on which [Jed] Hoyer wouldn’t budge: an opt-out after 2026.”

The inclusion of the opt-out clause turned out to be the pivotal point in the negotiations. Chicago’s general manager, Jed Hoyer, apparently wasn’t willing to concede on that front, and as a result, Imai ultimately took the Astros’ offer.

Why the Cubs Were Reluctant to Include the Opt-Out Clause

The refusal to include an opt-out clause after the 2026 season now makes more sense. For the Cubs, this was likely a strategic move to maintain some level of control over the long-term stability of their pitching staff.

By allowing Imai to opt-out after just one or two seasons, the Cubs would be putting themselves in a vulnerable position if the pitcher performs well in his rookie season. If Imai exceeds expectations in 2026, there’s a high likelihood he would exercise the opt-out, leaving the Cubs with a significant gap in their rotation.

Adding to the complexity, Chicago already faces a potential exodus of starting pitchers after the 2026 season. Jameson Taillon, Matthew Boyd, and Shota Imanaga are all set to become free agents after this upcoming season, and the Cubs are looking to ensure some continuity at the starting pitcher position. By avoiding the opt-out clause, they could secure a longer-term solution in Imai and avoid entering another offseason in need of multiple starting pitchers.

The Strategic Considerations Behind Hoyer’s Decision

While the Cubs’ decision to walk away from the deal may seem frustrating given how close they were to landing Imai, Hoyer’s reasoning is rooted in a long-term strategy. The Cubs are aiming to build a stable rotation without the constant risk of turnover due to short-term contracts or opt-out clauses.

This approach is also consistent with the Cubs’ front office philosophy of avoiding highly flexible contracts that could leave the team exposed in the future. Given the uncertainties that come with the volatility of free agency, especially with a high-risk player like Imai, the Cubs are likely focused on building a more sustainable pitching staff that they can rely on for multiple seasons.

At the same time, it’s clear that Imai’s potential as a top-tier pitcher could have been a game-changer for the Cubs’ rotation. The fact that they were in such close proximity to signing him shows that the Cubs had a clear vision for strengthening their staff this offseason — but ultimately, they had to weigh the risks of a short-term contract with a potential superstar against the long-term stability of their pitching depth.

The Cubs’ Offseason Outlook: Moving Forward

Despite missing out on Imai, the Cubs are not without options. The team’s front office has a history of finding value in the market, particularly in lower-risk signings that can pay dividends in the long run. The Cubs will likely continue to explore ways to bolster their rotation through trades, free-agent signings, and development within their farm system.

Additionally, the Cubs are still in a solid position to compete in the National League. With young stars like Nico Hoerner and Seiya Suzuki providing a core for the team, Chicago’s roster has the potential to make noise in the postseason, provided they can shore up the pitching staff.

While losing Imai is certainly a setback, it’s not a catastrophic one. The Cubs’ future remains bright, and there will undoubtedly be more opportunities to add key pieces to the team before the start of the 2026 season.

Conclusion: The Cubs’ Near-Miss with Imai and the Road Ahead

In the end, the Cubs’ failure to sign Tatsuya Imai boils down to a classic case of agent negotiation tactics. Scott Boras played his hand expertly, leveraging the Cubs’ offer into a better deal with the Houston Astros, and ultimately, Imai’s desire for an opt-out clause led him to sign with Houston.

For the Cubs, this represents another offseason of near-misses and cautious decision-making. While the Imai signing would have been a major boon for their rotation, Chicago’s focus on building for the future — even if it means missing out on a coveted player — shows their commitment to long-term success.

Looking ahead, the Cubs will continue to search for ways to improve their roster, knowing that every decision made in the offseason will affect their chances of returning to postseason glory. Though they missed out on Imai, the road to success is still open, and the Cubs will be ready for whatever challenges lie ahead.