Why Not Signing Tatsuya Imai Will Be Cubs’ Biggest Offseason Regret

As the Chicago Cubs reflect on their offseason decisions, one choice stands out as a potential game-changer they failed to make. While securing an NL Wild Card berth and clinching an opening-round win against the San Diego Padres was a solid step forward, “solid” simply wasn’t enough for a Cubs team with aspirations of reaching the ultimate destination—the World Series. In fact, their season ended in disappointment when their division rivals, the Milwaukee Brewers, eliminated them in the NL Division Series last October.

In the front office, Jed Hoyer, the Cubs’ President of Baseball Operations, took a proactive approach this offseason, adding talent with the goal of bolstering the roster for a deeper playoff run. However, despite making several impactful moves, there’s one significant player the Cubs failed to sign that will surely haunt them when the season concludes.

A Busy Offseason: Cubs’ Moves and Their Impact

After the Cubs’ early exit from the postseason, Hoyer knew changes were necessary. He acted swiftly in the offseason, securing some big-name acquisitions that were supposed to catapult the Cubs into the next level of competition. Alex Bregman, the star third baseman, was a key target, and Chicago ultimately lured him to Wrigley Field on a five-year deal.

In addition to Bregman, Hoyer traded away three promising prospects, including outfielder Owen Caissie, to the Miami Marlins for Edward Cabrera, a starting pitcher who will help solidify the rotation. With four new relievers signed and potential bench pieces like Tyler Austin and Chas McCormick added, it looked like the Cubs were setting themselves up for success in 2026.

Yet, despite these moves, one glaring missed opportunity still stands—one that could have made the Cubs’ offseason truly complete. The signing of Japanese pitcher Tatsuya Imai, an ace who was highly sought after, could have been the final piece to strengthen their rotation.

The Missed Opportunity: Why Cubs Should Have Signed Imai

Although the Cubs were heavily linked to Imai throughout the offseason, the Houston Astros ultimately made the move, securing the Japanese pitcher on a three-year deal worth $63 million. For the Cubs, missing out on Imai may turn out to be their biggest regret. The terms of the deal were not unreasonable for Chicago to match, and the Cubs could have bolstered their rotation with a star who has shown tremendous promise in the international scene.

Now, with Cabrera already part of the team, the Cubs’ starting rotation is full. But could they have shifted their focus by signing Imai, thus enabling them to make another move? Perhaps they could have dealt one of their current veterans, like Shota Imanaga or Jameson Taillon, to further optimize their roster.

Depth in the Rotation: A Critical Factor for Success

Depth in the starting rotation is more critical than ever for postseason success. Just take a look at the Los Angeles Dodgers, who have leveraged their pitching depth to win back-to-back World Series titles. Teams like the Toronto Blue Jays, Boston Red Sox, and New York Yankees have also seen success by utilizing young pitchers like Trey Yesavage, Connelly Early, and Cam Schlittler, all of whom contributed to their playoff runs.

The Cubs’ need for a sixth starter—or even just an additional depth piece—became even more apparent when considering how other teams were able to manage their pitching staff. Signing Imai to a three-year deal worth more than the $63 million the Astros offered would have been a no-brainer for Chicago, strengthening their rotation and providing depth that could prove invaluable in the long run.

Why Imai Would Have Fit Perfectly with the Cubs

Imai’s skillset could have meshed perfectly with the Cubs’ rotation. His dominance in Japan’s NPB and his well-rounded arsenal of pitches would have added a unique dimension to their staff. Coupled with Justin Steele—who’s expected to return in 2026 after his recovery—Imai could have provided the Cubs with a powerful 1-2 punch that could rival any rotation in the league.

The Cubs are entering the 2026 season with a competitive edge but missing one key element that could have helped them get over the postseason hump. It’s hard to ignore the fact that, had the Cubs signed Imai, they would have been in a far stronger position heading into the season. Instead, they are left to wonder “What could have been?”

What’s Next for the Cubs?

So, where do the Cubs go from here? They will proceed into the season with the current rotation, plus Justin Steele—whose return from injury is a hopeful boost. The rotation is certainly better than it was last season, but is it enough for a deeper playoff run?

If the Cubs’ pitching staff struggles, and if they fall short again in October, the image of Imai wearing the Houston Astros’ navy and orange will surely haunt Cubs fans for years to come. What could have been a new era of dominance in the Windy City could now just be a regretful missed opportunity.

The Impact on Cubs Fans and Future Moves

Cubs fans have been waiting for the team to return to the World Series for years, and the addition of Imai could have made that dream closer to reality. With the Astros already bringing in Imai, Chicago may have to come to terms with the fact that another team has made the moves they should have. This could be a tough pill to swallow as the season progresses.

Chicago’s front office will need to move fast in future offseasons, especially if they want to maintain relevance in the ever-competitive NL Central. While the Cubs are still a team with playoff potential, the signing of Imai would have been the move that set them apart from their competition.

Looking Ahead: Will This Be the Cubs’ “What If” Moment?

As the 2026 season draws nearer, Cubs’ fans will be left wondering whether missing out on Imai will be the “What if?” moment that defines this era of Cubs baseball. A powerful pitcher like Imai could have pushed the Cubs into the elite tier of the NL, but now, with their rotation set, it will be up to Hoyer and his team to prove that they can make a World Series run without him.

Only time will tell whether the Cubs’ decision to let Imai slip through their fingers was a minor setback or a major regret. Cubs fans are hoping it’s the former, but the reality may be much harsher—especially if the Astros’ ace becomes a key piece to another playoff contender’s success.

The Cubs are undeniably better after this offseason, but they could have been so much more. And that’s what will likely sting the most as the season progresses.

For Cubs fans, the question remains—did they make the right call, or will the regret of not signing Tatsuya Imai loom large as their season unfolds?