Beyond the New York Yankees’ shocking postseason result, their off-season plans are already shaping up to be as shockingly chaotic! It is no secret that now Brian Cashman is reportedly looking for a major clubhouse overhaul, and that includes a hard look at their starting pitching depth. But before the pinstriped office can even make a move, one of their top targets might be slipping through their fingers.

The San Diego Padres, Dylan Cease. 

Cease, who earned $13.75 million this season, is expected to command a huge payday in his free agency. Spotrac, in fact, expects him to land a $158.5 million deal for six years; that’s roughly about $26.4 million annually. For the Yankees, the price might sting, but given that Carlos Rodon and Max Fried stumbled so poorly in the ALDS, they might not have a choice but to invest. But the Cubs are circling like eagles and can hijack Cease from under the Bronx Bombers.

And honestly, the Cubs could use Cease more than anyone.

They have had a scrappy 2025 postseason. They survived two elimination series before being eliminated by the Brewers, finally. Their pitching looked battered and thin. In the end, they had two starters who were reliable—Jameson Taillon and Matthew Boyd. So, pitching depth is their No. 1 priority, and they might even have the money for once to chase the elite arms.

That is exactly where Dylan Cease comes in.

In a recent appearance on 670 The Score Inside the Clubhouse, MLB insider Bruce Levine mentioned that the Chicago Cubs are indeed among the top runners for Cease.

“According to MLB insiders I know, people in the know in other organizations, they feel the Cubs will be there among the top suitors (Dylan Cease) … I would say it’s highly likely – like for sure – that he’s going to be looked at by the Cubs and be continued to be pursued,” Levine mentioned, as transcribed by Bleacher Nation’s Michael Cerami.

Cease for sure didn’t have his best year this season and finished with a 4.55 ERA across 32 starts. But his strong finish of 2.76 ERA after September 1 just reminded everyone of the level of ace he is.

Plus, he is just 30 years old and still very durable, and not to mention, he has one of the best swing-and-miss arms available.

The Chicago Cubs have, for the longest time, been linked to top-tier starters, but they have not really signed. So the intention seems murky, but this time, the Yankees are distracted with their internal cleanup. And with them needing a frontline ace, the stars might just align perfectly for the Cubs to snag Cease.

The New York Yankees have eyes on Detroit’s ace!

The New York Yankees have never been the group to shy away from chasing the stars. So this winter, they might chase one of baseball’s best left arms—Tarik Skubal.

Jim Bowden mentions that the Tigers are likely to explore trade options for Tarik Skubal for the upcoming winter meeting and that the Yankees are “obviously” interested in the deal. And you can almost see Skubal in pinstripes and that 97 mph fastball blazing in the Bronx.

This is the type of move that Yankee fans want, and it is understandable why.

The 28-year-old has been great this season and posted a 2.21 ERA over 195.1 innings. This also makes him one of the most consistent aces. He doesn’t just overpower batters; he dissects them. He struck out 11.1 per nine innings while barely walking anyone! His command sits in the 97th percentile, and he is durable, intimidating, and efficient.

But like Cease’s case, too, this story might be all down to the dollars.

Skubal is under team control through 2027, but the Tigers and the ace might be far apart from signing a long-term deal, more so given that he is a Boras client. So this might crack open the trade market, and this is when you bet Brian Cashman will be watching.

The price, no doubt, would be steep. Detroit might likely even demand a package with Will Warren, Jasson Domínguez, and top prospect Carlos Lagrange. It will be a tough call, and the Yanks will need to decide whether to give up on the future for a win-now ace. And who knows? The fanbase is tired; they haven’t won since forever, so maybe they would bite the bullet.