The Offseason of Uncertainty...

 

Will the Yankees make the moves that make the difference in 2026?...

This is a weird offseason. I legitimately do not know if the New York Yankees will move to fill holes without completing the puzzle to ensure more regular season success and a roll of the dice for the October Crapshoot, or if the Yankees recognize the ownership groups in Los Angeles (Chavez Ravine, not Anaheim) and Queens have set a new World Order, forcing the team to go “all in”. Granted, the Mets flunked the season, but it will not stop Uncle Steve from throwing more of his money into the problem. Sunday’s trade of outfielder Brandon Nimmo to the Texas Rangers for second baseman Marcus Semien puts them in the outfield arena for guys like Kyle Tucker and Cody Bellinger. 

The Yankees do not seem to be on the same playing field with the game’s best, even if they historically have been Major League Baseball’s most fantastic franchise. You have owners who play to win, and you have owners who play to profit. While you could argue that a World Series Championship pays the most significant dividends, it involves too much gambling, particularly for a conservative, professionally trained bean counter like Hal Steinbrenner.

Hal Steinbrenner (Photo Credit: Dustin Satloff/Getty Images)

I blame George Steinbrenner for not training a son to hold his same passion. That was what he was trying to do with a former son-in-law, although divorce tanked the plan. Hank Steinbrenner’s son, George IV, holds the magic name. I have no idea whether he keeps his grandfather’s (or his father’s) passion. Yet, I am ready for the next generation of Steinbrenners to ascend to the throne. Hal was not interested in the Yankees when he was young, and I pray he is working on an escape plan. I am surprised that selling the team does not appeal to Hal. I know, he holds his father’s legacy in his hands, but a sale would bring multi-generational money to the Steinbrenner family. Every year, I hope Hal decides to go “all in” like he did in 2009. Maybe this is the year, maybe not. Realistically, the latter seems like the most probable outcome…and I come away from the offseasons with a sense of disappointment.

Sadly, we move forward with Hal’s leadership, for better or for worse. A transition to a younger owner is years away. So, we are married to him and can only hope that the Steinbrenner blood works into some future decisions. 

As for the team, the offseason is well underway. A few moves have already been made. Trent Grisham, surprisingly, accepted the Yankees’ qualifying offer. He must have felt the compensation that interested teams would pay to sign him as a potential market suppressor. If he can replicate his productive 2025 in 2026, he will enter the free agency period next offseason with no strings attached. Not sure if this is one of those ‘bet on yourself’ moments, or if Grisham was not ready to end his Yankees tenure. I suspect it is the former regardless of how Grisham feels about the Yankees.

I have mixed feelings about Grisham. If he can replicate his performance next season, a one-year deal is not a terrible thing. The money that goes to Grisham could have been used to attract an elite free agent like Kyle Tucker. The Yankees can afford both, but recent history says the team will choose a cheaper route. I would love to have Cody Bellinger back in Pinstripes, but Tucker is better. I would hate to see the Yankees try to chase Tucker, fail, and lose Bellinger while they were grasping for Tucker. Admittedly, I would go with the surer thing and try to bring back Bellinger. I have seen many fans say the contract will age poorly, but at this point, I am concerned about 2026. We are not making moves for 2027 or 2028.

Somehow, Boston always seems to get out from under bad contracts, but the Yankees bite the bullet and eat the money.

Grisham’s return spells the end for Jasson Dominguez unless the Yankees pass on both Tucker and Dominguez and need a left fielder (again). A trade of either Dominguez or Spencer Jones this offseason seems likely. I would hate to see Jones leave. I remember when people were complaining about a young Aaron Judge striking out too much. He has had a nice Major League career, one that has guaranteed a trip to Cooperstown, New York, someday.

The Yankees also re-signed Clarke Schmidt to a $4.5 million deal for the 2026 season. Schmidt had Tommy John surgery in July, and I feared a potential non-tender, like how they have moved on from other Tommy John rehabilitators like Nathan Eovaldi. I can hear GM Brian Cashman now, “He’s like a trade deadline acquisition” when Schmidt returns mid-season. I am glad to see Schmidt returning, and I am sure his return will coincide with a rotation need.

Oswaldo Cabrera, who missed most of last season, also re-signed for $1.2 million. While I like Cabrera, his role could be upgraded. The Yankees need a shortstop to start the year, and if they acquire a legitimate frontline shortstop, keeping Jose Caballero in reserve, it would be hard to find a place for Cabrera on the Major League roster. Shortstop is a sore subject. I know the Yankees love Anthony Volpe, but the team can do better.

The Yankees re-signed LHP Ryan Yarbrough, a dude who knows his role and does it well. With the starting pitchers who will be late arrivals in the 2026 season, it's all-hands-on-deck for the Yankees' rotation. Yarbrough is not the answer, but he helps. 

There were a few surprises with the non-tenders. I got the decision to cut bait with Michael Arias, Scott Effross, and Ian Hamilton. The two that surprised me were Mark Leiter, Jr., even if he did fade in the second half, and Jake Cousins. Cousins underwent Tommy John surgery in June, so like Clarke Schmidt, he is out until the second half of 2026. Holding two positions for guys who cannot help when the season begins must have been too much for Brian Cashman and his cast of nerds. I wish it worked out for Leiter, Jr., or Cousins, but I know protecting roster spots over the Winter is challenging when other moves are anticipated. Bullpen will undoubtedly be an area of focus this offseason as the Yankees try to build a strong pen after last season’s struggles.

The Yankees tendered contracts to eight arbitration-eligible players. Second baseman Jazz Chisholm, Jr., closer David Bednar, set up reliever Camilo Doval, shortstop Anthony Volpe, utility infielder Jose Caballero, starter Luis Gil, setup reliever Fernando Cruz, and deadline-disappointment right-hander Jake Bird.

The Yankees also selected the contracts of outfielder Spencer Jones and pitchers Chase Hampton and Elmer Rodriguez in advance of next month’s Rule 5 Draft.  After watching catcher Carlos Narvaez thrive with the Boston Red Sox this season, there is consolation in the fact that the Red Sox gave us a pitcher who can ascend to the top of the pitching prospects in the organization. Rodriguez is currently the third-ranked prospect in the Yankees organization behind Jones and RHP Carlos Lagrange, according to MLB.com. I thought they would protect a couple of other prospects, but I trust they had their reasons.  I hope none of the non-selected players come back to haunt the Yankees. They are RHP relievers Harrison Cohen and Eric Reyzelman; LHP Henry Lalane (once highly regarded), LHP Brock Selvidge, and LHP Allen Facundo (not on MLB.com’s prospect list, but a talent that has drawn strong reviews); first baseman T.J. Rumfield; outfielder Jace Avina; and catcher Manuel Palencia. It seems like a few of these guys will be poached in the Rule 5 Draft. Whether they stick with their new teams remains to be seen, but they will be playing for an opportunity that the Yankees either could not or did not afford.  No doubt the Boston Red Sox will be rummaging through the Yankees’ trash looking for another ex-Yankee difference maker.

Tough decisions. I recognize that we cannot judge today’s decisions until we see the moves the team makes between now and Opening Day. The chances for success in 2026 hinge on the collective improvements made to the roster, not a few surprising individual moves in November.

Congratulations to Aaron Judge for winning the 2025 American League Most Valuable Player Award. My fear was that the voters would be unduly influenced by the historic season of Seattle Mariners catcher Cal Raleigh. He certainly went where no catcher has ever gone before, but Aaron Judge was the better overall hitter and deserved the award. The only thing that Raleigh did better than Judge, aside from the homers, was taking his team to the American League Championship. I still laugh when I remember people saying that Aaron Judge will never be Mike Trout. In retrospect, I am glad he is not Mike Trout, an injury-riddled 30-something former elite player. In Trout’s defense, I would love to see him rebound with one of his best seasons next year (so long as it is not at the Yankees’ expense). I have no idea what it must be like for him to watch his friend Shohei Ohtani win a World Series Championship every year since his departure from the Los Angeles Angels of "an hour away" Anaheim. I genuinely wish Trout could have been given better opportunities to win during his career.

As for moves to be made this offseason, I would love splashy moves, but those days are over. I quietly hope for Kyle Tucker, but I hope for at least the return of Cody Bellinger. I would like to see the Yankees bring in another Japanese player to re-establish the intense connection they once had with Japan. The Yankees have not had a Japanese player since Masahiro Tanaka departed (Kenta Maeda’s brief stint in the minors last season does not count). I would like to see the Yankees sign Tatsuya Imai. I recognize the 27-year-old righthander is not elite, but I want to think he can be as valuable as Hiroki Kuroda once was. I have cooled on Munetaka Murakami, a first baseman who can also play third base, so that I would take Imai as the preferred Japanese player over Murakami. Murakami was recently photographed having dinner with Los Angeles Dodgers pitcher Yoshinobu Yamamoto, leading to speculation the Dodgers will continue to add to their elite Japanese connection. This is the magic the Yankees once held when Hideki Matsui was on the roster. The Yankees need to re-engage the Japanese community and make New York as attractive as the West Coast.

Tatsuya Imai (Photo Credit: Sports Nippon/Getty Images)

Usually, I am anxious and excited for the Baseball Winter Meetings. It has always been my favorite time of year. This year is different. I am unsure what to expect from Yankees leadership. Will they try to run it back with the majority of the 2025 roster, or will they legitimately make the moves to close the gap with the game’s elite teams? I have no idea or trust in the Yankees’ leadership to do what it takes.

Hopefully, a month from now, we will have a better idea of the team’s direction and plans to compete in 2026. If late December is just as foggy, it sadly does not bode well for 2026. So, either MUCH happens between now and then, or there are crickets with the Yankees hierarchy. Hal, please make us believe in the Yankees again. This is your birthright.

As always, Go Yankees!