Chicago Cubs predicted to lose Tarik Skubal free agency sweepstakes

Entering the offseason, the Chicago Cubs’ top priority is bolstering their pitching rotation. Their crown jewel in free agency would be two-time Cy Young winner Tarik Skubal.

But the Cubs won’t be alone in that pursuit. He’s had a sub-three ERA with at least 185 strikeouts the past three years. His entire seven-year MLB tenure includes a 3.02 ERA and a 1,075/199 K/BB ratio over 163 games. Skubal is considered one of the best pitchers in the league and would immediately become essentially every team’s ace.

If the Cubs want him, they’ll have to be prepared to spend the bag. But their need is clear. Shota Imanaga, Kevin Gausman, Matthew Boyd and Clay Holmes are all set to hit free agency. While Chicago wants to maximize their talent in the rotation, they need enough bodies for the unit in the first place.

Until Skubal puts his name on the dotted line, the Cubs will be considered a contender for Skubal. But there may be more enticing options out there.

Chicago Cubs bested in Tarik Skubal battle

The San Diego Padres are in a similar situation to the Cubs. They want to make a serious push to the playoffs but are in need of pitching; especially with Michael King entering free agency. Signing Skubal would be an easy way to fix those problems. Plus, the Padres would be stealing him away from their rival Los Angeles Dodgers.

When the dust clears, Kerry Miller of Bleacher Reports argues the most likely scenario is Skubal signing with San Diego.

“Assuming Michael King opts out, the Padres are going to lose six of the seven pitchers who made at least nine starts for them in 2026,” Miller wrote. “They also can’t possibly know what they are going to get out of Joe Musgrove and Yu Darvish in 2027, at which point the starting rotation becomes Nick Pivetta, Randy Vásquez and three big question marks.

“Even though they do have a ton of money tied up in Manny Machado, Xander Bogaerts, Fernando Tatis Jr. and Jackson Merrill through 2033 and beyond, they simply have to swing big for arguably the best pitcher in the sport today,” he continued.

With the Cubs and Padres both in desperate need of pitching, the Skubal sweepstakes could turn into a bidding war. The left-handed is already expected to earn arguably the richest contract in this year’s free agency class.

If Chicago were to miss out, they’d have plenty of extra money to build out their rotations. But there aren’t many configurations that’d look as strong as with Skubal leading the charge.

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