Breaking down Yankees' possible plan beyond 2026 if they 'run it back'

Since 2017, the New York Yankees have been one Aaron Judge away from essentially masquerading as the LA Angels. We will say, the 2018 and 2019 teams were genuinely very good, but 2020-2025 has largely been a horror show, as was 2011-2016.

It feels like each and every offseason since 2017, the Yankees have been in some sort of transition period, possessed glaring weaknesses that the front office refused to address, or opted to pass on generational talents (Bryce Harper, Manny Machado, Corey Seager, Kyle Schwarber, etc.).

And here we are, still waiting for any signs that this organization has a desire to win a World Series in 2026 (or at all) during Judge's prime years. All New York has done this offseason is bring back a handful of players from the 2025 roster (Tim Hill, Paul Blackburn, Trent Grisham and Amed Rosario) and sign a few guys to minor league deals. They seem to have accidentally invested over $22 million for one year of Grisham, and have doled out a grand total of $7.5 million on the other three players.

Meanwhile, other big-market teams have made one or more impactful moves despite the free agent and trade markets being slow. Almost everybody else has figured out a way to create a lane and get stronger while the Yankees wait for their preferred opportunity. But will that even come?

Cody Bellinger remains a free agent. Same with Kyle Tucker, Alex Bregman, Bo Bichette, JT Realmuto, Kazuma Okamoto, Ranger Suarez, Tatsuya Imai, Framber Valdez, and others. The Yankees have been linked to Bellinger and Imai, but it appears as if they have drawn a line in the sand with Belli and have been wavering on Imai, if the latest buzz is to be believed.

If there's little interest in the other remaining free agents, in addition to not much going on as it pertains to the trade market, then what's the Yankees' plan to maximize Judge's remaining MVP years? That's where fans start looking back on previous offseasons and trade deadlines and mutter, "yup, that was it, we missed it."

Breaking down Yankees' possible plan beyond 2026 if they 'run it back'

Maybe the Yankees are looking to invest minimally this offseason and prepare for ... we don't know. Is it 2027? Is it 2028 and beyond? The picture is murky, especially when you dive into future free agent classes and possible trade targets on middling teams.

Because, while bringing Bellinger back is a good thing, it does not change the complexion of the Yankees whatsoever. It simply allows them to maintain the status quo, which was a very good regular season team — not immune to prolonged slumps and inexplicable play — and a really underwhelming playoff team.

Yankees' 2026 payroll and beyond

Right now, the Yankees' luxury tax payroll figure sits at $286 million, according to FanGraphs' Roster Resource. That number drops to $190 million in 2027, $153 million in 2028 and $90 million in 2029. Cot's Baseball Contracts has similar projections as well.

Some notable contracts include Giancarlo Stanton's 13-year, $325 million deal coming to an end after 2027, in addition to Ryan McMahon's six-year, $70 million agreement. All of Grisham, Jazz Chisholm and David Bednar will be free agents after 2026.

Financial flexibility! That's never a bad thing! Well ... it is when there's not much to spend the money on. Plus, losing Chisholm and Bednar will create serious voids on the roster. The biggest name in next year's free agent class is Tarik Skubal, and we'd bet almost anything on the fact the Yankees will not pay him the money he wants. Outside of that, there's little to look forward to.

But what about 2027? Steven Kwan, Logan Gilbert, Jeremy Peña, Joe Ryan, Adley Rutschman, and a lot of veterans who will be over the hill. And 2028? Shea Langeliers, Vinnie Pasquantino, Jose Ramirez, Gunnar Henderson, Hunter Brown, Logan Webb and Edward Cabrera. Not the worst in the world, but certainly not star-studded, beaming with multiple elite options!

As for trade targets, they aren't even worth speculating upon because it's a total crap shoot in regard to who might be made available. The Yankees can't be operating in the world of hoping a random All-Star becomes attainable at an unknown juncture.

Future Yankees free agents

We'll lay it all out for you here so you can see the departures and money being freed up.

2026-2027

• Trent Grisham — $22.02 million
• Ryan Yarbrough — $2.5 million
• Amed Rosario — $2.5 million
• Tim Hill — $2.5 million
• David Bednar — ~$9 million
• Jazz Chishom — ~$10 million

2027-2028

• Giancarlo Stanton — $22 million
• Ryan McMahon — $16 million
• Clarke Schmidt — ~$6 million
• Camilo Doval — ~$8 million

2028-2029

• Gerrit Cole — $36 million
• Carlos Rodón — $27.83 million
• Anthony Volpe — TBD
• Luis Gil — TBD
• Oswaldo Cabrera — TBD
• Fernando Cruz — TBD
• Jake Bird — TBD

Yankees' short-term outlook with remaining Aaron Judge, Gerrit Cole years

• 2026

As for 2026, it very much feels like the Yankees will let the offseason market come to them. If it works in their favor, then they might make a few impact additions. If it doesn't, Cashman and Co. will be totally fine rolling toward Opening Day with whatever they have. They'll see what the deal is until June before they start swinging deals and preparing for the trade deadline (even though history says they won't do much). Also, don't forget, they will be relying on young players like Anthony Volpe, Austin Wells, Ben Rice, Cam Schlittler, Jasson Dominguez, Spencer Jones, Will Warren, and others to take big steps forward this year and next. As history would have it, that's a terrible blueprint for New York. Very few of their prospects pan out. Say a prayer that turns a big corner.

• 2027

Maybe at this point they reach some sort of a buyout/trade situation with Stanton to clear more space for spending. There is just no way the veteran slugger will be helpful by that time, given how his body has betrayed him alongside the reality that he makes the lineup less flexible by clogging the DH spot. As for supplementing his past production? Not entirely sure how they'll do that with what could be an all-time top-heavy free agent class. This is why signing someone like Seager before the 2022 season feels even more disastrous. But hey, maybe all of Rice, Schlittler, and one of Wells/Jones/Dominguez are bonafide stars by then.

• 2028

Ditto for the young players turning into stars. And maybe they add one of Ryan/Gilbert to prepare for the departures of Cole/Rodón? Then look to the trade market to supplement at the deadline? Perhaps they bring in Kwan (everybody's wish for 2026) and shift one of Jones/Dominguez to center field with Bellinger (assuming he comes back) to first base on a regular part-time basis? Or maybe Jones/Dominguez are already in center because Bellinger never re-signed and Grisham left after 2026. Is there a new Japanese star ready to come to MLB between 2027 and 2028? Could that really turn the tides? Do they sign Jeremy Peña and simply non-tender Volpe, if they don't already do that or trade him by 2027?

• 2029

Will Gunnar Henderson save the team by then with Judge in his age-37 season? Will Jose Ramirez in his age-36 season be the Josh Donaldson-esque move of 2029? Do they steal a legitimate Cy Young contender in Hunter Brown away from the Astros? Logan Webb from the Giants? And even if they did get Henderson, Brown and Webb, how much does that inspire you?

The modern day Yankees represent regret, agony and "what could have been." And most of that was a direct result of arbitrary financial restrictions, beginning when they cut payroll after the 2017 season — the year they came within a game of the World Series — to reset the luxury tax. They added no pitching until 2020 when they signed Gerrit Cole, and from that point forward it's largely been ill-advised free agent signing after ill-advised trade candidate as they let the better fits and household names find new homes elsewhere.

So, what's the plan to make sure Aaron Judge secures a ring to cement his legacy? We don't know, and we're pretty sure the front office doesn't, either.