If you have been screaming at your phone wondering why the Yankees haven’t backed a Brink’s truck up to Cody Bellinger’s front door yet, you might want to take a deep breath and look at the bigger picture. The MLB offseason has moved at a glacial pace, a frustrating reality for fans who want instant gratification, but a strategic masterclass for front offices willing to wait out the market.
According to ESPN insider Jeff Passan, the stalemate isn’t about teams being cheap; it is about top-tier offensive talent realizing their self-valuation doesn’t match reality.
Passan’s recent report paints a clear picture of a market in correction mode. “Same as what’s going on with Kyle Tucker and Alex Bregman and Cody Bellinger: What they believe they’re worth has not been matched by teams,” Passan noted. This disconnect is the exact friction point General Manager Brian Cashman has been exploiting all winter. The Yankees have a number in mind for Bellinger, and they simply aren’t going to bid against themselves when the rest of the league is seemingly just as hesitant to meet the astronomical asking prices.
The Rise of the High-AAV “Pillow Contract”
We are watching a shift in how these mega-deals play out, and it might play right into New York’s hands. Passan suggests that “it’s reasonable to think at least one will slip between the cracks and go for a shorter-term, opt-out-heavy deal we’ve seen work for Pete Alonso, Matt Chapman and, for pitchers, Blake Snell.”
This trend of shorter, high-average-annual-value deals allows players to bet on themselves, but it also allows teams to avoid the crippling backend of decade-long contracts that rarely age well.
For a player like Bo Bichette, whom Passan highlights as a prime candidate for this structure, it makes sense to rebuild value and hit the market again at 28. But for Bellinger, who is looking for long-term security after already proving his bounce-back capability, falling into this category would be a massive win for the Yankees. If his market collapses to a shorter-term deal, Cashman gets the impact bat he needs without the terrifying long-term risk.
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Patience Is the Only Strategy That Makes Sense
This context explains why a recent Yankees Cody Bellinger update takes a positive turn for those hoping to see him back in pinstripes.
The Yankees aren’t being “cheap”—they are reading the room. If Kyle Tucker and Alex Bregman, arguably more consistent commodities, are struggling to find their desired numbers, Bellinger’s camp has very little leverage to demand a massive overpay.
Cashman has often been criticized for moving too slowly, but in this specific winter, his inactivity looks like discipline.
The Yankees know Bellinger fits their roster perfectly; his lefty swing is tailor-made for the short porch, and his defensive versatility is a necessity. But they also know that no other team is rushing to give him seven or eight years. By waiting, the Yankees are forcing the market to come to them, potentially saving millions that can be reallocated to pitching depth or trade deadline acquisitions. It is a dangerous game of chicken, but right now, the Yankees aren’t the ones blinking.