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3. Chicago Cubs
You can make a case the Cubs should actually be No. 1 on this list, considering how good their lineup and defense are -- and how many questions their injury-riddled pitching staff has. As it stands, Chicago’s top two starters are Matthew Boyd and Shota Imanaga. Those two pitchers' struggles last October were a big reason why the Cubs lost to the Brewers in the NL Division Series. The third option? Either Colin Rea, David Peterson or Edward Cabrera, who is currently on the IL.
That said, with the state of their pitching, they might be more than one starter away from being a World Series contender, potentially giving them less urgency to compete with other teams in the Skubal sweepstakes. (And, unlike the next two teams on this list, they’ve actually won a World Series fairly recently.)
2. Tampa Bay Rays
The Rays have proven that you don’t need a big payroll to win in the regular season -- the hard part is finishing the job in October. Though Tampa Bay has been one of baseball’s best-run organizations for years, the franchise’s first title has remained elusive. But that door is wide open in 2026.
With the American League lacking in elite teams, the Rays have as good a chance as any AL club to reach the Fall Classic, especially if they add Skubal to a rotation that already includes Drew Rasmussen, Shane McClanahan and Nick Martinez. (The back injury that forced McClanahan from Thursday's start is also worth watching as the Skubal sweepstakes heats up.)
1. Milwaukee Brewers
The Brewers have made the playoffs in eight of the past nine years, but they haven’t reached the World Series since 1982 and are also one of the handful of franchises without a title. They finished with MLB’s best record last year, only to be swept by the Dodgers in the National League Championship Series.
We understand the Brewers’ reluctance to surrender controllable young talent for a rental when they play in a small market, but at some point, you’ve gotta go for it. And a rotation led by Skubal and Jacob Misiorowski could be exactly what they need to overcome Los Angeles and win it all. If the Brewers don't swing a deal for the Tigers ace, they'll be left crossing their fingers that Kyle Harrison can return healthy from his forearm injury -- and that they don't end up crossing paths with Skubal as an opponent come October.