Hal Steinbrenner loves to say that a $300+ million payroll is not required to create a contender. That's true. But it's certainly required to turn this version of the Yankees into a contender, based on the funds they've already allocated and the roster holes that still remain. This is what they never seem to understand.
The Yankees don't have to wield a $500 million payroll and steamroll the rest of the league to be championship-caliber, either. They can trade from their farm rather than splash cash, if that's how they wish to operate. While it might be popular to dream of blowing the doors off and adding a $40 million AAV at every single position, the bare minimum fans want to see is a willingness to leverage their finances to paper over the types of mistakes the might sink lesser teams. This is what the Yankees are supposed to be. An $18 million pitching contract might destroy the Milwaukee Brewers if it goes wrong. The Yankees? Despite what some want you to believe, they profit. Nobody wants to write off an expensive flop, but they can do it. They must do it. It's the singular advantage big-market teams most plainly have at their disposal.
The Dodgers sign Michael Conforto. It fails. No matter; they continue pushing at the trade deadline and beyond. After all, it was their decision to allocate $17 million that way, secure in the knowledge that they could swallow the cash and overcome their self-created hurdle, if need be.
The Yankees? They're not so willing.
We didn't advocate against taking a chance on Marcus Stroman because he might've boomed or busted; that was obvious. That is the nature of free agency. We worried about the move because we knew the Yankees would later use Stroman's money as an excuse not to add further and reinforce a different area of the roster/the back half of the rotation, if needed. That's exactly what happened. They held their own decision against themselves. Somehow, they turned a complementary move/risk into a self-made wall. They did it with DJ LeMahieu in the early 2020s. They did it with the Aaron Hicks extension. The Yankees love nothing more than to create roadblocks of their own making, rather than acknowledging a less-than-ideal reality and moving past it.
And they've got another such instance brewing with their interest in Bo Bichette, paired with Ryan McMahon and his money, as the entire front office asks, "Who did this to us?" without identifying themselves.
The Yankees don’t view Bo Bichette as a short stop, and would likely need to move Ryan McMahon or Jazz Chisholm Jr, if acquired, according to @Ken_Rosenthal. pic.twitter.com/JFR4YPZBKx
— The Yankee Report (@YankeeReport_) January 5, 2026
Yankees letting Ryan McMahon get in the way of Bo Bichette pursuit
According to Ken Rosenthal's latest, the Yankees continue to be interested in acquiring Bo Bichette in free agency, but don't believe in him as a shortstop option. That would mean they would need to clear either Jazz Chisholm Jr.'s final campaign under control, or McMahon's two years at $16 million, in order to find a fit. Knowing how the Yankees operate, it would seem ... less than likely that they'd bring in both Bichette and Cody Bellinger without clearing some existing money.
Again, for what feels like the millionth time, this means that the Yankees have authorized the acquisition of significant money tied to a flawed player — McMahon, a defensive wizard with 20-homer power, but suspect and below-league average offense overall — then allowed their own trade to hamstring their roster mere months later.
McMahon is a solid player. He brings sturdy defense and a lefty bat that can hook loopers into the short porch. He's a professional. He certainly provided the Yankees with a breath of fresh air down the stretch. But ... they knew what they were getting into with McMahon. They were choosing to harm their own pursuit of ducking the luxury tax with a player who wouldn't be able to fulfill their wildest dreams. They were adding money at the 2025 deadline that would either lead to them blowing past certain financial thresholds when an upgrade opportunity like Bichette presented itself in the offseason, or would result in them eliminating themselves from certain markets with a preemptive and incomplete strike. Guess which direction they seem to be leaning towards?
In the same way that the Yankees have declared they "don't want to pay more to add to a rotation that already includes three $20+ million pitchers" (goodbye, Imai, and apologies to a rotation in turmoil), they don't seem to want to add non-Bellinger money on offense, either, without a corresponding departure. That departure won't be Trent Grisham — they willingly paid him, too, then let their own purposeful commitment halt them at the gate and create an offseason full of half-measures.
Again, we're not asking for wild spending. We're only asking that significant financial allocations for flawed players be met with the corresponding willingness to add additional finances to escape any problems that arise. The Yankees are one of very few teams that can swallow their pride and write the check. Continually, they refuse, leaving themselves in the precarious position that so many small market teams find themselves stuck in, hamstrung by a single risk.
