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Three Sleepers Loom Before Tarik Skubal's Free Agency Frenzy

The Tarik Skubal sweepstakes is going to be fascinating to follow.
Los Angeles Dodgers pitcher Tarik Skubal (29) throws a pitch in the second inning of the MLB National League game between the Cincinnati Reds and the Los Angeles Dodgers at Great American Ball Park in Cincinnati on Monday, Sept. 14, 2026.
Los Angeles Dodgers pitcher Tarik Skubal (29) throws a pitch in the second inning of the MLB National League game between the Cincinnati Reds and the Los Angeles Dodgers at Great American Ball Park in Cincinnati on Monday, Sept. 14, 2026. | USA TODAY Network via Reuters Connect

The Tarik Skubal sweepstakes in free agency is going to capture the attention of baseball fans across the league until the day he puts pen to paper and signs a deal.

Skubal is a two-time Cy Young Award winner and is still just 29 years old. He's entering free agency at a perfect time and will cash in, likely with a historic deal that breaks the record for the largest contract for a starter in big league history to this point. It helps for him that the free agency class is extremely weak this offseason. Skubal is the clear leader of the group and the early market projections paint the picture of a player who is about to be very, very rich.

As rumors have grown, naturally the Los Angeles Dodgers and the New York Mets have been talked about as the likely landing spots the most. While projecting the Skubal sweepstakes, ESPN's Kiley McDaniel pointed to three sleepers as well.

Los Angeles Angels

Los Angeles Angels hat
Sep 4, 2026; Pittsburgh, Pennsylvania, USA; Los Angeles Angels hat and glove in the dugout before the game against the Pittsburgh Pirates at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | IMAGN IMAGES via Reuters Connect

The Angels have new ownership with Stan Kroenke taking over. That should give Angels fans hope. He's someone who has had success everywhere he has gone, and he isn't afraid to spend. The Angels have been brutal in recent memory. If Kroenke wants to fix that, he'll need to bring stars to town. Pitching has been a serious issue for the organization. Adding Skubal would certainly change that.

Chicago White Sox

Chicago White Sox hat
Jul 15, 2023; Atlanta, Georgia, USA; A detailed view of a Chicago White Sox hat and glove in the dugout against the Atlanta Braves in the first inning at Truist Park. Mandatory Credit: Brett Davis-USA TODAY Sports | USA TODAY Sports via Reuters Connect

This would be an absolute blast. The White Sox won 84 games in 2026 and shocked the baseball world. This is a team that had been racking up 100-loss seasons left and right. Then, all of a sudden they turned into a playoff team in 2026 and made it pretty far. The White Sox's roster is full of young, cost-controlled players. Most of the core pieces were actually acquired throughout this rebuild as Chicago traded stars away. Pitching is the organization's biggest hole. Skubal would be expensive, but would give the team an ace to build around for years to come.

San Diego Padres

San Diego Padres hat
Jun 17, 2022; Denver, Colorado, USA; A detail view of a San Diego Padres hat on a glove in the dugout in the ninth inning against the Colorado Rockies at Coors Field. Mandatory Credit: Isaiah J. Downing-USA TODAY Sports | USA TODAY Sports

The Padres are a peculiar team to mention in the Skubal sweepstakes. McDaniel listed them as one of the three sleepers. ESPN's Jeff Passan also mentioned the Padres as a potential option for Skubal, but didn't use the word sleeper. On one hand, the Padres are loaded and have spent big in the past, which would make them seem like an obvious landing spot. But with financial questions for the organization, can they handle another massive deal? That's what likely makes them fit more into the sleeper category, but AJ Preller can never be fully counted out.

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Patrick McAvoy
PATRICK MCAVOY

Patrick McAvoy's experiences include local and national sports coverage at the New England Sports Network with a focus on baseball and basketball. Outside of journalism, Patrick also received an MBA at Brandeis University. For all business/marketing inquiries regarding Fastball On SI, please reach out to Scott Neville: scott@moreviewsmedia.com