MLB free agency began two and a half months ago. The New York Yankees only just reunited with Cody Bellinger on Wednesday (Jan. 21). The rest of the Yankees' offseason? Trent Grisham, Ryan Yarbrough, Amed Rosario, Tim Hill, Paul Blackburn, Kaleb Ort, Paul DeJong, Cade Winquest and Ryan Weathers. Does that sound like things will be much different than 2025?
The overwhelming response from fans is "no, not at all." The organization probably has different thoughts, though, believing all they'll need to do is make the playoffs again. Because, famously, all bets are off once you get to the playoffs. It's anybody's game. While that philosophy is not misguided, it simply doesn't apply to the Yankees in any capacity, considering how often they have fallen short in the postseason since 2010, and even more so as the field expanded.
Yankees letting Cody Bellinger and Scott Boras eat away their offseason may
The problem with the Yankees hasn't been their talent. It hasn't been their ability to perform well in the regular season. It's been their presence in October, likely fueled by a stale front office approach that no longer targets specific personalities — why pay attention to who a human is when you already know their home run totals or can see their potential upside saving you millions of dollars?
Another part of that problem has been getting stuck in negotiations with baseball's anti-hero, Scott Boras. For whatever reason, the Yankees have found themselves getting caught up with this man far too many times, and they didn't even have the decency to capitalize on Boras when he was down bad in other offseasons (Bryce Harper, Cody Bellinger Part 1, Blake Snell Part 1, just off the top of our heads).
Back in 2019, he had them bid against themselves with Gerrit Cole, leading to an excessive $100+ million overpay, according to reports. Then came the Carlos Rodón situation that ended in a ridiculous, drawn out stare-down that saw the Yankees foot a $162 million bill (an objective overpay but one fans accepted because of the starting rotation need). You all know what happened with Juan Soto last year. And then there's Bellinger.
The Yankees wanted Bellinger. Bellinger wanted the Yankees. The fans wanted Bellinger. It was all right there. But the business of baseball took over, sacrificing weeks upon weeks of constructive roster decisions as Boras fought tooth and nail to squeeze a few (irrelevant) million dollars out of Hal Steinbrenner. Don't get us wrong, we're pro-player when it comes to any labor discussion, but you'll start to lose us when you're quibbling over what ends up being chump change in a nine-figure contract.
We don't know where these negotiations began, but we can assure you they didn't start below the $125 million range, or else Boras and Bellinger would've almost certainly made it a point to sign somewhere else. Do we know that for certain? No, but we know how disrespectful lowballs can greatly impact a relationship.
Nonetheless, because the Yankees have been so careful with their spending limits, it didn't allow them flexibility while they were trying to figure out how to add/subtract without Bellinger in the fold. The possibility of him not returning gave them $25-$35 million in excess spending ... but what if he decided to come back after the Yankees had spent that money? Would Hal Steinbrenner kick his 200-pound golden chair and break his big toe? Oh great, just what they needed: more healthcare costs!
Part of the problem was perhaps mistakenly earmarking $22 million to Trent Grisham via the qualifying offer. Part of the problem was perhaps the belief that neither Gerrit Cole nor Carlos Rodón will miss a beat after returning from major surgeries. Part of the problem was perhaps the market moving slowly due to the lack of obvious fits and truly elite talent.
Whatever it may be, there is no doubt that the most impactful occurrence of them all was the "move that made the most sense" taking 75 days to be finalized. Countless insiders and personalities dubbed this the most likely high-profile reunion of the offseason ... but somehow it seems that talks were contentious rather than seamless, thus erasing weeks off the calendar.
That allowed the Yankees to play the waiting game, which is their preferred method when they get uncomfortable. Instead of finding innovative ways to combat obscure happenings or bad luck, the Yankees will let the chips fall where they may before they scrape up whatever's left.
In this case, they did get the ultimate prize in their eyes, but it was at the cost of the rest of the roster benefitting. This Yankees team is no different than the one that got trounced by the Blue Jays in the ALDS. We understand they'll now be getting a full campaign out of the group they acquired at the trade deadline instead of just an August-October test run. Not to mention, they rid themselves of a few sunk costs. But that doesn't feel like it's enough to power them past a number of teams that were better than them last year (and got better than them this offseason).
Bellinger got his money. The Yankees got their guy. On that front, all is well. But the damage to the 2026 Yankees may have already been done if this was the last piece of major maneuvering we should expect to see.
