My Yankees Offseason Plan

Yankees Offseason Plan

…October Thoughts from Cary Greene

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That I’m writing this so soon, long before the 2026 postseason is even over, can only mean one thing - the Yankees got eliminated by “the better team.” Again. Oy vey! C’mon man! Are you kidding me? Obviously not.

My last piece, the End of the Season Assessment went live this past weekend. I’m on to bigger and better things now. As Bruce Buffer would say, “IT’S TIME!” I apologize on the Yankees behalf, to all the SSTN fans, that this topic is being brought up today, but it’s all I’ve got folks. Shall we then?

In last weekend’s assessment, I wrote that….All Yankees fans know this, because Hal has taught us to know this over the years. He’s not a guy who will swing for the fences and go for broke. He does spend though, but only up to a point. He’s not willing to part with his profits in order to put the Yankees over the top because that’s not what owning the Yankees is about to him.

On that note, Steinbrenner, to his credit, sold a 16% stake in the team to Apollo Global Management this year, which will infuse the Yankees with $2.6 Billion that they can devote to operating expenses and purportedly - this rather large chunk of change may also go in part towards boosting the Yankees payroll in the coming years. Perhaps this will go down as the best thing Hal Steinbrenner ever did? Time will tell, there’s no guarantee that spending more money will win that elusive 28th World Series title that Yankees fans want so badly, but an extra $2.6 billion can’t hurt, right? 

We know Aaron Boone and Brian Cashman are both coming back, so the leadership changes most of us here on SSTN recognize needed to happen were rejected by Hal Steinbrenner. He likes his front office and he’s doing what he always does, he’s standing pat. However, maybe this will finally be the offseason where we witness the Yankees spend like their pants are on fire. Maybe, thanks to the $2.6 billion cash infusion courtesy of Apollo, the Yankees brand will be shaped back into that of a championship outfit.

Am I delusional to think this? I may be. If there is a season, if a new CBA can be struck between the Owners and the Players Association, what will it look like? The Owners are clamoring for a salary cap. Will there be a salary floor as well? There is lots to be determined so we’ll all have to wait to see how it all shakes out, but for now, here are the areas that need to be addressed on the Yankees roster.

The reason for the postseason failure was that the Yankees slightly below regular season offense wilted as the pitching it faced got better and better. The Yankees were methodically dissected by a Rays team that just wouldn’t take their foot off the gas. The Yankees defense was also far too sloppy when it mattered most.

We know Jazz Chisholm, Trent Grisham, Paul Goldschmidt, Amed Rosario, Ryan Yarbrough, Tim Hill, Michael Fulmer are now all free agents and likely they’ve all played their last games in pinstripes.  It also seems very likely that Ryan McMahon will be released and very possibly, this may finally be the offseason where the Yankees send Giancarlo Stanton packing as well.

Bringing back the team’s closer, David Bednar, will likely be at the top of Brian Cashman’s to-do list. Paul Blackburn is also a free agent and the Yankees will probably try to sign him as well this offseason. The Yankees will clearly need to spend a significant sum this winter, far more than they’ve spent thus far in the Boone era. Assuming they’re willing to spend,  which is an adventurously ample axiom, what are going to be the team’s priorities?

#1 - Dramatically Improving the Offense

The Yankees need to focus on injecting their offense with firepower. If they DFA Ryan McMahon - and make no mistake, they should - the Yankees will need to fix a position of importance that has plagued the team since the days of Alex Rodriguez. It’s high-time that the Yankees addressed third base properly. Teruaki Sato, the NPB Triple Crown winner, has been cleared to be posted. Sato also won a Gold Glove award at third base in 2025. Sato is as close a must sign free agent this season for Brian Cashman as there has been in recent memory. The Yankees desperately need to reengage with NPB stars, thinking back to the last time the Yankees won the World Series in 2009, the MVP of the fall classic was a former NPB star - Hideki Matsui.

Typically, Sato bats in the heart of the order for the Hanshin Tigers, though he did bat second for Japan’s star-studded WBC team. His combination of power and ability to drive in runs makes him a candidate to bat cleanup for the Yankees, but it may make even more sense to bat him third.

With third base fixed, thanks to the Yankees signing Soto, the next move the Yankees should make is to sign their longtime nemesis, Randy Arozarena. He’s not a strong defender in left field, but throughout his career, he’s handled right field pretty decently. Arozarina’s bat fills the Yankees need for right-handed pop and not only is he insurance for the next time Aaron Judge goes on the DL, but he also replaces the Yankees need for Giancarlo Stanton. Adding both Sato and Arozarena brings a ton of run production to what was unfortunately nothing more than a slightly below average offense last season.

Also, Aaron Judge’s best days are likely behind him and it would be prudent for the Yankees to act decisively this offseason to fortify the heart of the lineup with adequate run production.

There’s no question that the Yankees also need a right-hand hitting catcher and now that Ryan Jeffers, who they wanted so badly at the Trade Deadline, is a free agent - Cashman might also look to sign him as well. That’s three very good offensive players, if all goes right. Is it enough to fix the Yankees offense though? Let’s see how the new lineup would look:

1.     Rice DH/1B

2.    Judge RF/DH

3.    Sato 3B

4.    Arozarena LF/RF/DH

5.    Bellinger CF

6.    Garcia Jr 1B/DH

7.    Lombard Jr SS

8.    Wells C

9.    Volpe 2B

That lineup looks pretty good to me, if I do say so. This is an infinitely more flexible lineup as well, without Giancarlo Stanton clogging things up at the DH spot.

2 - Address the Bullpen

With the offense retooled, the Yankees would then need to re-sign David Bednar. He’s been a great fit for the Yankees, as I said he would be all along -  years before they finally traded for him. Still, it should be noted that the only reason Cashman finally traded for him is that he was the least expensive to acquire closer available at the 2025 Trade Deadline. In recent times, Cashman has been opposed to spending significant monetary resources on the bullpen. It’s probably time for Cashman to change his thinking a little bit here. However, I have always liked the idea of killing multiple birds with a single stone, so hear me out on this next idea.

3 - Upgrade the Rotation

If the Yankees were to sign Mike King, it would be a massive upgrade to their starting rotation and the silver lining would be that it would push both Ryan Weathers and Will Warren into bullpen roles. With Bednar cemented as the closer, the Yankees could then focus on not only bringing back Paul Blackburn, but they could also sign Adrian Morejon.

Ultimately, I’m advocating for Cashman to sign three bullpen pieces - Bednar, Morejon and Blackburn and also, a front of the rotation starter in King. All total, that’s a whopping 7 free agents I feel the Yankees need to sign - if the goal is to actually compete for and likely win a World Series. The Yankees need to get back to being the Yankees, not some team comprised of players acquired out of desperation at Trade Deadlines and several AAAA type prospects cobbling the rest of the veteran roster together.

The Casualties

You may have noticed, my plan doesn’t involve Spencer Jones. It became obvious in the playoffs that he had a very hard time with the elite pitching that was eating him alive high in the zone. He needs more time at Triple-A, where he can play regularly. Also, I don’t feel like Jasson Dominguez has much of a future left with the Yankees. He only has one remaining option and he’s running out of time in pinstripes. His trade value is also at an all-time low as well, so the Yankees will likely leave him in Scranton and hope for a miracle from him.

There will be a number of failed prospect casualties if the Yankees retool in order to try to win a championship. Guys like Luis Gil, Yerry De los Santos, Angel Chivilli and a few others are clearly players the Yankees will soon be leading to the slaughterhouse that is the auction place ahead of the Rule 5 Draft. Cashman will attempt to obtain a few lower level prospects for many of these names and if he fails to do that, then they’ll be exposed to the Rule 5 Draft along with a host of other Yankees. I actually have an article coming out soon on the Rule 5 Draft, so stay tuned for that!

Now that my offseason plan is finalized way too early, its time to start the discussion. What do you think of the plan and also, what plan would you like to see Brian Cashman implement. Will Cashman be able to spend big this offseason? I’m hoping so, but the ramifications due to the as yet to be agreed upon and entirely new CBT certainly could cause spending to completely freeze until such time as this is figured out.