Tarik Skubal Sweepstakes Early Sleepers Would Shock MLB

Where will Tarik Skubal go this winter? Three sleepers would certainly surprise the league.

Oct 3, 2026; Los Angeles, California, USA; Los Angeles Dodgers pitcher Tarik Skubal (29) throws during the sixth inning of game one of the NLDS against the Atlanta Braves for the 2026 MLB Playoffs at Uniqlo Field at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images | IMAGN IMAGES via Reuters Connect

The 2026 Major League Baseball postseason is in full swing and will last at least a few more weeks before the talking points around baseball shift completely towards the offseason, free agency and the looming labor battle.

The guy to watch will be Tarik Skubal. He's the straw that will stir the drink in free agency. For over a year at this point, his looming stint in free agency has been discussed because he could be on his way to a historic deal. Back in September, ESPN's Jeff Passan shared a column with intel on free agency and noted that if there's no salary cap, Skubal's ultimate deal could rise as high as double the $245 million deal Stephen Strasburg got back with the Washington Nationals. On Friday, ESPN's Kiley McDaniel shared a column centered around Skubal's free agency with industry insiders weighing in. Interestingly, the three "sleepers" that were mentioned were the Los Angeles Angels, Chicago White Sox and the San Diego Padres.

"Sleepers: The Los Angeles Angels, Chicago White Sox and San Diego Padres were mentioned in this category; the Angels and Padres have new ownership, and the White Sox have a new owner in waiting," McDaniel wrote. "In most high-end free agent bidding processes, there's at least one surprising or mystery team. After circling back with some sources after the projections were in, the Padres seemed to be the consensus pick for the most serious bidder in this group."

Where Should Tarik Skubal Go?

Oct 3, 2026; Los Angeles, California, USA; Los Angeles Dodgers pitcher Tarik Skubal (29) throws during the first inning of game one of the NLDS against the Atlanta Braves for the 2026 MLB Playoffs at Uniqlo Field at Dodger Stadium. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images | IMAGN IMAGES via Reuters Connect

If Skubal were to land with any of these three teams, the decision would send shockwaves across baseball. Over the last few months, unsurprisingly, teams like the New York Mets, Los Angeles Dodgers and even the New York Yankees have been floated as fits for the ace. Plus, a team like the Toronto Blue Jays. All big-market teams with big wallets.

If Skubal goes to a team like that, it would be the rich getting richer. The White Sox have been the darlings of the 2026 playoffs so far. They're loaded with young talent and are back in the playoffs to the surprise of pretty much everyone. This is a team that lost 102 games last year and 121 games in 2024. Imagine if all of a sudden, they had Skubal anchoring the rotation? They would be a World Series contender immediately.

The Padres are a club that has been loaded, but it has been talked about consistently that they have big contracts on the books and need to square away their financials. If all of a sudden, you add potentially the largest contract for a starter in history to the books, that'd be a surprise.

Then, we have the Angels. Los Angeles has been brutal for years at this point. Skubal is the type of hurler that could change their fortunes.

It's still early and free agency hasn't even started, but these are the types of rumors that are far more interesting than Skubal landing with the Dodgers or Mets.