Baseball fans enjoyed the return of two teams to the playoffs in 2025 — the Cubs and Tigers.

The teams have some history together, having faced each other in four World Series. The Chicago Cubs beat the Detroit Tigers in 1907 and 1908. However, the team didn’t have the same fortune in the next two meetings, losing in 1935 and 1945.

Fast forward 80 years later to present day 2025, and the Cubs could get the Tigers back by plucking one of Major League Baseball’s most talented starting pitchers from them — Tarik Skubal.

The 2024 AL Cy Young Award winner is still under contract with Detroit for one more year. However, if the Tigers can’t agree on a long-term deal with Skubal, he could be available before the end of the 2026 season.

Thus, it’s worth Chicago asking Detroit how much they want for their prized starting pitcher.

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Chicago has already seen one of their own pitchers choose to seek another team in 2026, and others could join him. But the Cubs will need to add to the pitching core for 2026, regardless.

Though it may take a little more than Imanaga, Ballesteros and a first-round draft pick to pry Skubal away from the Tigers, it’s a great starting point or first offer. If the 2024 AL Cy Young Award winner leaves Detroit in free agency this time next year, then his current team could potentially get nothing (or next to it) for him.

In this trade, the Cubs would rid themselves of Imanaga’s contract. Imanaga becomes expendable, or any other veteran starter for that matter. Keep in mind, Chicago is anticipating a healthy return of Justin Steele in 2026 as well.

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The emergence of rookie Cade Horton has executives and fans in Chicago howling for more after an impressive 2025 season. And with outfielder Kyle Tucker expected to leave the Cubs this off-season, the team can afford to pay Skubal a pretty hefty contract.

Even without Tucker, the Cubs still have center fielder Pete Crow-Armstrong, veteran Ian Happ, and Seiya Suzuki. Moises Ballesteros makes the deal enticing for the Tigers if Imanaga is not to Detroit’s liking. Or it may take fellow outfielder Owen Caissie. Or both.

Detroit may not want to pay the big bucks for Skubal. One reason the Tigers haven’t made the World Series since 2012 is their lack of spending. They got swept 4-0 against the San Francisco Giants.

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Chicago made the playoffs for the first time in four years this season. They had the fourth-best record in the NL and look to capture the NL Central from Cubs manager Craig Counsell’s former team, the Milwaukee Brewers.

Should a trade be agreed upon before next season, a one-two punch of Horton and Skubal certainly makes the Cubs one of the favorites in both the NL Central Division and all of MLB. Steele and Matthew Boyd would round out the starting pitching rotation for Chicago.

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