Yankees fans are all too familiar with the infamous “Yankees Tax” in trade negotiations—an inflated asking price simply because it’s the Yankees on the other end of the phone. Nobody wants to make life easier for Brian Cashman or help New York get better. It’s just the way it is.
However, the Yankees managed to pull off the Juan Soto trade with the Padres last year thanks to a perfect storm of circumstances. San Diego needed to clear payroll with Soto set to earn around $30 million in arbitration, and they desperately needed pitching depth, which the Yankees had in abundance. The deal ultimately came together as a win-win for both sides.
This time around, though, things are different. The Padres have other prized assets, like Dylan Cease and Luis Arráez, who won’t be as easy to acquire. Cease, a Cy Young-caliber right-hander owed roughly $14 million in 2025, is reportedly on the trade block along with Arráez. Both players would be perfect fits for the Yankees, but there’s a catch—New York might not have the right pieces to get a deal done, especially with AL East rivals like the Red Sox and Orioles lurking.
We’ve already seen Boston pay a hefty price to land Garrett Crochet, and now the Orioles, armed with one of the best farm systems in baseball, are eyeing Cease. The good news for the Yankees? Trade talks between Baltimore and San Diego aren’t going well. According to Orioles insider Roch Kubatko, the Padres are demanding a return that includes top names like Samuel Basallo, Jordan Westburg, or Coby Mayo. So far, Baltimore has refused to include any of them.
For context, Westburg was an All-Star in 2024 at just 25 years old, while Basallo and Mayo consistently rank among the Orioles’ top three prospects. That’s a steep price, and Baltimore’s front office doesn’t seem willing to part with their cost-controlled young talent.
This is a positive development for the Yankees heading into 2025. The Orioles need to capitalize on their current window of contention, with stars like Adley Rutschman, Gunnar Henderson, Colton Cowser, Jackson Holliday, and Westburg still on team-friendly deals. Now’s the time for them to make bold moves, but if history is any indicator, Baltimore’s front office lacks that sense of urgency.
The Orioles have fizzled out in back-to-back postseasons, failing to win a playoff game since 2014 and getting swept in their last four series. If that’s not enough to trigger some aggressive decision-making, it’s hard to say what will. For now, though, the Yankees can breathe a sigh of relief as the Padres hold firm in trade talks and the Orioles hesitate to push their chips to the center of the table.