Chicago Cubs tied to Detroit Tigers’ Tarik Skubal in fantastical trade scenarios

The Chicago Cubs finished the 2025 season with a defiant run in the NLDS against the Milwaukee Brewers, battling back from a 0-2 deficit in the best-of-five series before eventually falling in Game Five.

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A big part of the team’s lack of playoff staying power had to do with their pitching.

By the latter part of the postseason, Cubs’ pitching was hobbled and limping into each subsequent game. By the end of the division series, Chicago was down to two trustworthy starting pitchers and maybe three relievers who could be depended upon in high-leverage situations.

A quick fix to this problem could lie just about four hours to the northeast of Chicago in Detroit.

The Detroit Tigers are in a tough position when it comes to their ace starting pitcher Tarik Skubal, who becomes a free agent at the end of next season and is predicted to land a history-making lucrative contract on the open market.

Tarik Skubal is a goner in Detroit

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The lefty will definitely be worth his monstrous payday as, perhaps, the best pitcher in all of baseball with a proven record of elite-level success. Skubal’s 3.08 career ERA is outstanding, but his last three seasons of sub-3.00 ERA excellence tell the tale of someone extremely special. This past season, by the way, just happened to be a career year with a 2.21 ERA over 31 starts and 195.1 innings.

There’s been a lot of buzz recently about the Tigers looking to trade their ace away for a haul of talent, in anticipation of his contract being too rich for them. One of the teams mentioned in conjunction with such a major trade is Chicago.

Chicago Cubs-Detroit Tigers trade proposals and fantasies

Really, what Cubs fan would NOT want to see Skubal in the blue pinstripes atop the rotation?

One proposed trade has the Cubs sending Shota Imanaga (and his complex calculus contract) to the Tigers, along with Moises Ballesteros and/or Owen Caissie and their first round draft pick. Another proposal has Cade Horton being packaged and sent to Detroit in a Skubal deal.

This talk is pure fantasy, though.

The haul required to entice the Tigers would be for just one year of the lefty ace. It’s a pretty sure thing that the Cubs would lose Skubal to free agency just as the Tigers would.

Still, the Cubs’ chances of postseason glory would look really good with a true ace at the top of the rotation.

The Cubs’ need for high-end pitching

Some of Chicago’s lack of pitching depth this past season was due to circumstance beyond the team’s control. This will be used as justification for not doing all that much this offseason.

Ace Justin Steele suffered a season-ending elbow injury in April, removing him from the mix entirely. Rookie sensation Horton, meanwhile, suffered a season-ending rib fracture late in the regular season after an unbelievable run of excellence throughout the second half of 2025.

It might be tempting to say that the Cubs’ postseason outlook would’ve been a lot different had Steele and Horton been pitching come October. That, however, would be letting the Cubs’ front office and ownership off the hook. They had plenty of opportunities throughout the year to add pitching depth to a staff that clearly needed reinforcement.

But 2026 offers a chance at a redo and the opportunity to do what they didn’t do in 2025.

With only one contract on the books after 2026 and enough of a budget to spend freely this winter, the Cubs could easily flex their major market muscles and sign some free agent pitching impact players. History tells us, though, that they probably won’t.

The other way to get that impact player is via trade.

The Cubs shied away from pulling the trigger on Jesus Luzardo last offseason. It would’ve been a more modest deal for two years of a high-tier starter than what the Tigers would demand for one year of Skubal. So, it’s just not likely that the Cubs will even remotely entertain the idea of a trade with Detroit.

Still, one can dream.

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Source: https://www.chicitysports.com/chicago-cubs-detroit-tigers-tarik-skubal-trade