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This offseason could lead to more disappointment for Yankee fans

The Yankees were once the villains of Major League Baseball. Will this offseason be a return to form for Cashman and Co., or more of the same?

New York Yankees v Washington Nationals Photo by Michael Reaves/Getty Images

I grew up outside of Toronto, where Blue Jays fans routinely accused the Yankees of supposedly “buying” their championships. My 12th-grade history teacher, a welcome voice of reason, used to say that getting mad at the Yankees for signing free agents to expensive contracts was as pointless as getting mad at a rich person for buying an expensive car.

Fast-forward 11 years. The Yankees have won exactly zero championships and I’m now a jaded old man yelling at a cloud. After yet another disappointing season in an unacceptably long line of disappointing seasons, Yankees fans are once again waiting with bated breath to see what the team does this offseason. Will they embrace their former status as league villain and make multiple big splashes in free agency? Or will they stick with their recent plan of avoiding the luxury tax and take on reclamation projects? Either way, what a difference a decade can make, eh?

From Jeff Passan’s belief that New York is the likeliest landing spot for Corey Seager to Bryan Hoch’s report that the Yankees have soured on Trevor Story, the time-honoured tradition of connecting every big free agent to the Yankees has officially begun. I hate to be the bearer of bad news yet again, but since the season can end as soon as tonight, it’s time to temper our expectations a little bit. While we all want to see the organization make a huge splash (or two), there are a few reasons to be pessimistic when it comes to this offseason.


The natural place to start is the payroll situation. FanGraphs estimates that the Yankees’ 2022 payroll already sits at $221 million, with over $132 million tied up in just 7 players (even excluding Rougned Odor’s salary, which is the Rangers’ responsibility). That is already a significant contribution of money from an owner who has shown a reluctance to go beyond the luxury tax. If Seager’s contract exceeds the $300 million mark that has been rumoured, that likely means adding another salary of upwards of $30 million to the books next season. Even if he doesn’t reach $300 million, he’ll likely get close. I’m not entirely sure that’s something that this front office will want — or have clearance — to do.

The next cause for concern is the ongoing CBA negotiations. The current CBA expires on December 1st at 12:01 am, and all signs seem to be pointing to a work stoppage. With no new CBA on the horizon and tensions understandably high between the owners and the players, there’s no guarantee that there will even be a 2022 season. This unpredictability is certainly going to affect every single organization and free agent this offseason, as the prospect of committing millions of dollars to big-name free agents, only to lose a season of revenue on a potential long-term work stoppage, doesn’t exactly seem enticing to owners.

Next, what about a certain notable player entering the last year of arbitration? If you look at the FanGraphs chart above, you’ll notice that Aaron Judge fits that bill. After an exceptional 2021 campaign, he is due for a big raise. Are the Yankees really willing to let the current face of the franchise walk in exchange for one of this offseason’s big-name free agents? Off the top of my head, the last time I can remember this organization shockingly letting a player of this caliber walk was probably when Robinson Canó left for Seattle, but his status and marketability never really reached the levels Judge has reached. I’ll ask it again: Are the Yankees really going to let him walk?

Then there’s the small problem of a little team called the Los Angeles Dodgers. Per FanGraphs, the Dodgers 2022 payroll projects to be $194 million. That is a far cry from their $282 million payroll in 2021. Translation: the Dodgers suddenly have a ton of money to spend. I know it sounds ridiculous, but the Dodgers have shown a clear refusal to restrict themselves to the luxury cap if it means having a legitimate shot at the World Series. In theory, then, the Dodgers can easily sign up to three top-flight free agents this offseason without batting an eyelash. Totally unrelated, but I now understand how it must’ve felt to be a Jays fans in the mid-to-late 2000s.

And, finally, there’s 2023. In 2023, Aroldis Chapman, Zack Britton, and Joey Gallo all hit free agency, which would free up roughly $40 million in salary for the organization. Do the Yankees pass on the (far superior) 2022 free agent class in an attempt to reset and spend big in 2023? I don’t think it’s particularly likely, but I also don’t think it should be ruled out as a possibility.

If I were a betting man, I would put my money on the Yankees signing one of the big shortstops — most likely Seager — and then making a number of smaller, less impactful deals to fill out the rest of the roster. However, I also wouldn’t be surprised if someone like Andrelton Simmons is this team’s starting shortstop in 2022 (or whenever the next MLB season starts). All I’m saying is this: With the offseason looming, don’t get carried away with your free agent expectations. If this organization has proven one thing to us fans over the last decade, it’s to not get our hopes up.