4 farm system-clearing trades that could save Yankees' championship window

The New York Yankees never fully rebuild, but we have seen windows open and shut. Re-tooling is probably the better term — turning over the roster and infusing it with young players. The last time the window needed to be reset, we saw the Yankees sell at the 2016 deadline. Most of those moves didn't actually pay real dividends, but they set the stage for Aaron Judge's ascension and the opening of the current window the club is navigating.

With the meat of the roster aging, we're likely going to see something similar happen again soon. Judge is still immensely productive, but he's entering his age-34 season. Gerrit Cole is 35 and coming off a major injury. Giancarlo Stanton hasn't been at his peak for a long time already. The list goes on and on.

But a big trade could help extend a run that hasn't been able to get to the finish line. Moving all their chips to the table could be the best way for the Yankees to maximize what's left of Judge's brilliance before Father Time takes hold. That would mean parting with significant prospect capital, something the club has been wont to do.

If Cashman does get inspired to make an unlikely swing for the fences on the trade market, which Baby Bombers would he be willing to pony up who also have the cache to bring back a superstar?

The obvious answer is Spencer Jones, whose midsummer hot streak helped to hide some of the concerns in his game. His value has never been higher. Additionally, the Yankees have an impressive collection of young arms, with Carlos Lagrange, Elmer Rodriguez, Bryce Cunningham, and Ben Hess all being names to watch. Towering, but oft-injured lefty Henry Lalane could also be intriguing, and position players like shortstop Kaeden Kent and outfielders Dillon Lewis and Brendan Jones could be worthwhile complementary pieces that could facilitate an earth-shattering move.

So let's suspend our sense of disbelief, throw budgetary restrictions to the wind, and take a look at some targets that would absolutely be game-changers for 2026 and the future.

4 targets the Yankees should sell the farm for in order to maximize the Aaron Judge era

Starting pitcher Tarik Skubal

The chances of this happening are minuscule at best, but in a fantasy world, how could you say no? Brian Cashman should call of Detroit Tigers president of baseball ops Scott Harris and simply say Take your pick.

Of course, the next part of this is actually keeping Tarik Skubal in the fold for the long run. You'd want to avoid another Juan Soto situation, where you're just renting an elite talent for a year. So, the next suspension of disbelief is that the Yankees would hand Skubal a $400 million check immediately after consummating the trade.

If they were to do this, however, they'd have arguably the game's best hitter and best pitcher at their disposal, and while you'd still need to build a quality team around them, that can mask a lot of ills.

Outfielder Fernando Tatis Jr.

The San Diego Padres have insisted that they won't trade Fernando Tatis Jr., and that could very well be true. However, the franchise has been mired in ownership drama, financial insecurity, and is said to be considering selling the team, so moving off of the remaining nine years and $292 million on Tatis Jr.'s contract would bring about some serious relief.

Besides, they're not going to come out and say we have to trade him and kill any leverage they have. Tatis Jr. turns 27 in January and is one of the most electric players in the game. It would take a pretty penny to convince San Diego to move him, but if the Yankees truly emptied the system, maybe it would be enough to entice them.

The added benefit is that this would be a window-spanning move. Once Judge begins to slow down, Tatis Jr. can step in and become the focal point and keep the championship hopes afloat. Sure, he'd need to move to the opposite outfield corner in order to co-exist with Judge, but that's a tiny hurdle in what would otherwise be a slam-dunk trade.

Shortstop Corey Seager

The Texas Rangers' motivation to move Corey Seager might not be as strong after the Marcus Semien trade, but they still have a lot of holes to fill and a pretty tight budget.

Swinging a deal for Seager would come with more risk than Skubal or Tatis Jr., given his injury history. The last time he played more than 123 games in a single season was 2022. But when he is on the field, Seager is one of the game's best, especially under pressure.

This would be righting a wrong from years ago, and as a result would finally free us from the Anthony Volpe experience. How can you say no to that?

Starting pitcher Freddy Peralta

In the superstar pecking order, Freddy Peralta is a cut below the other three on this list, but that's not really a slight against him as much as it is an acknowledgment of the others' greatness.

This also would be the most financially feasible move for 2026, though. Like Skubal, Peralta would require an extension for this to work to the Yankees' long-term benefit.

One could argue that after a year in which Peralta hit career-bests in innings pitched (176 2/3) and ERA (2.70), the best lies ahead for the 29-year-old, and he'd certainly provide the top-of-the-rotation stuff as a righty that Gerrit Cole might no longer have.

The old adage "pitching wins championships" has become a cliche for a reason: it works, and adding another ace to the equation can only help keep the window open as the other, older hurlers on the roster begin to decline.