An NL Wild Card berth and subsequent opening-round win over the San Diego Padres would lead many fans to say the Chicago Cubs had a solid season. Unfortunately, “a solid season” is not what the Cubs had in mind. A World Series berth was the ultimate goal. Unfortunately, their division rivals, the Milwaukee Brewers, dispatched the North Siders in one of the NL's Division Series matchups last October.
Under the leadership of their president of baseball operations, Jed Hoyer, the Cubs had an active offseason. The team made multiple additions, including two big moves that should help move the needle considerably. Last month, Chicago finally reeled in star third baseman Alex Bregman, bringing him to Wrigley Field on a five-year deal. Hoyer also used 2026's first month to improve the starting rotation, trading three prospects, including outfielder Owen Caissie, to the Miami Marlins for starting pitcher Edward Cabrera.
Four new relievers were also signed, in addition to potential bench pieces in Tyler Austin and Chas McCormick. As the Cubs look to improve on a solid 2025 campaign, there's not too much that Hoyer and company can do at the moment. However, one free agent starter could have bolstered their rotation even more. Despite being linked to Japanese star Tatsuya Imai all offseason, the Houston Astros inked the import to a three-year deal. That is one move that the Cubbies will regret not pulling the trigger on when the upcoming season is all said and done.
Cubs could have bolstered rotation with two new additions
While missing out on Imai could have led directly to the Cabrera trade, the terms under which the Japanese ace agreed to with the Astros should have been easy for the Cubs to match. With Cabrera now in the fold, it appears Chicago's rotation is full at the moment. However, an Imai signing could have led to the North Siders trading another veteran, like Shota Imanaga or Jameson Taillon.
Even if Imai became the Cubs' sixth starter, it's been clear that starting pitching depth is pivotal to October success. The Los Angeles Dodgers have used that depth to help propel them to back-to-back World Series titles. The Toronto Blue Jays, Boston Red Sox, and New York Yankees' usage of rising rookies Trey Yesavage, Connelly Early, and Cam Schlittler helped fuel their playoff runs as well. Inking the incoming Imai to a three-year deal for more than the $63 million that the Astros gave him should have been a no-brainer for Chicago.
However, the deal never happened. Imai will ply his trade in Houston for the next three years. The Cubs will move forward with their current rotation, plus lefty Justin Steele, who will return at some point in 2026. Will it be enough for a longer playoff run in October? If not, the image of Imai in Astros' navy and orange may haunt Chicago and its fans for years to come.
