Free Agent Fallout

Andy Singer

January 17th, 2026

I had planned to write a very different article today. That post was about analyzing and projecting the improvements that Ryan Weathers could make in pinstripes and my reaction to that trade. That article will post sometime next week, because after a wild 36 hours on the free agent carousel, somehow my analysis of Ryan Weathers just doesn't seem timely.

The Dodgers once again swooped in and signed the best players available by flexing their financial muscle. The Mets reacted by making a similar move for a player who might be even better. What have the Yankees done? Played at the margins. That's what frugal, mid-market teams do. It's pathetic to watch from the sidelines as a Yankee fan.

Kyle Tucker was the best outfielder available on the free agent market by a longshot. The Yankees have signaled their desire for an outfielder. Kyle Tucker hits left-handed with a swing designed for Yankee Stadium. The Yankees have spent their offseason courting the return of a left-handed hitting outfielder with a swing built for Yankee Stadium. As I showed a few weeks ago, Kyle Tucker is a far superior hitter to Cody Bellinger, even in a year that was a down-year by his standard.

As I wrote in the article linked above, I also noted that Bo Bichette might have actually been the best fit for the Yankees. The Yankees' ideal lineup includes a right-handed hitter who makes good swing decisions and also makes tons of contact with enough pop to do some damage. Ideally, it would be a player that could pair with Judge at the top of the lineup. Bichette is 100% that type of player. I heard plenty of rumblings this offseason that Bichette wouldn't be willing to move to 3B. I had comments come into the SSTN Mailbag indicating the same, wondering why I would even ponder something so unlikely. The Mets snagged Bichette...to play 3B. If you think Ryan McMahon is a real impediment to signing someone else to play 3B, I have a bridge to sell you.

As I watched these moves unfold yesterday, it finally sank in the extent to which the Yankees have become just another team. Don't get me wrong, baseball's system works far different now than it did during even the last Yankee dynasty, and I agree that makes it harder to build a dynasty. However, it is equally clear that creating a dynasty is not ownership's greatest concern.

Brian Cashman and the front office, regardless of what many believe, are not stupid. Do you really believe that Cashman doesn't realize that Bo Bichette or Kyle Tucker are better investments than Cody Bellinger? Particularly when we project those two over the next 3-4 years over Bellinger's next 5-7? Of course Cashman and the front office can do that math. We all can. However, it is almost certain that when Cashman checked in on his available options, he quickly learned that it would take either a very long contract or an absurdly high AAV, something Yankee ownership could not accept.

Much has been written about the manner in which team owners are preparing for the coming CBA negotiations. Yes, no team seems to want to hand out a deal longer than 5 years, which tells you something about the tactic the owners are sure to use during the next round of labor negotiations. Teams like the Dodgers and the Mets have found a way to have their cake and eat it too. The Yankees? Sure, they'll stick to 5 years or less for any free agent deal...as long as it fits Steinbrenner's self-imposed budget.

Why else would the Yankees allow their offseason to be dictated and engulfed by the 6th best free agent on the market? Steinbrenner and Cashman can say there is no defined budget until they're blue in the face, but the Yankees' inaction says otherwise. Yes, the Steinbrenners have spent a ton of money on the Yankees, no question. From a marketing perspective, they don't have a choice there. They have to spend at least in the ballpark of what the other largest market teams do in order to maintain their mystique and sell season ticket packages and advertisements to corporate entities. Winning within that framework is the front office's job.

I don't believe the Yankees need to buy championships and I'm also not wistful for the days of yore when George Steinbrenner ran the team. We've white-washed so much of that history as we watch the Yankees sit on their hands. The team has young players that can be exciting; a homegrown star that has eclipsed almost every other player's performance over the last couple of decades; and a team that is terribly close to being good enough to win it all with some help. That Steinbrenner won't reach into his pocket for just a little more each of the last 5-7 years is just ridiculous.

Hal Steinbrenner has made a miscalculation. The Yankee mystique that he's maintained is indeed fading. I've heard from more Yankee fans who are losing interest than at any time in recent memory. It wouldn't be hard to get those fans back: do something. Prove you're willing to put your money where your mouth is when it comes to winning. None of us are interested in listening to an owner in the largest market in sports hem and haw about whether he's making a profit.

There were glaring opportunities this offseason to give Aaron Judge a better shot at a ring. Steinbrenner chose not to help him out. I fear Aaron Judge will become the next tragic figure in Yankee history. The team can still get better and fight for a World Series title; I still believe that. I also am still looking forward to watching the team this summer, despite my feelings on this offseason. But I don't want to hear that ownership cared about winning. If this team wins, it's on everyone in the organization except for ownership.