As Brian Cashman answered questions about the Yankees’ financial flexibility this offseason, one inquiry wondered if he’d be willing to offer a nine-figure deal for the right fit.
“I would always do that,” Cashman said with a smile in mid-November, well-aware that targets such as Cody Bellinger and Tatsuya Imai will cross that threshold. “I’m good at spending money.”
AdvertisementAdvertisementAdvertisementThat last line served as a joke, a nod to the Yankees’ penchant for having one of baseball’s highest payrolls throughout the general manager’s tenure, which has spanned over a quarter of a century. However, fans reeling from an ALDS playoff exit were quick to dispute Cashman’s not-so-serious self-assessment on social media, arguing that their team wouldn’t be stuck in a 16-year championship drought if the shot-caller used the mega-millions at his disposal in wiser fashion.
Of course, exorbitant spending — the Yankees have had a top three competitive balance tax payroll the past four seasons and are poised to exceed $300 million for the third consecutive year in 2026 — doesn’t guarantee titles.
The Dodgers have pushed back on that, securing two straight World Series with a top two payroll in 2024 and a major league-leading $415.2 million payroll in 2025, per Cot’s Contracts. Still, Yankees owner Hal Steinbrenner insisted there is a “weak correlation” when it comes to “spending the most money and winning a championship” after stating his team had a $319 million budget in 2025.
“There was nothing low about my payroll and the Mets’ payroll,” Steinbrenner added over Zoom last week, making sure to mention that the Yankees’ crosstown rival missed the playoffs despite spending $338.2 million last season. “Look where we ended up.”
AdvertisementAdvertisementAdvertisementWith Steinbrenner also calling the Yankees’ profitability into question and noting that a lower payroll would be “ideal” — though unlikely — it would be reasonable to think he is unhappy with the way his money has been used over the years.
But when asked about that, he didn’t vocalize any issues with Cashman’s allocation of funds.
“The intent was certainly there, and the research and the homework was certainly there. I can’t complain about that,” replied Steinbrenner, who blamed his players for the Yankees’ shortcomings in 2025. “You’re always looking hindsight, right? Hindsight is 20-20. Certainly, some things haven’t worked out. But it’s not for not doing the research and the homework and everything else.”
Steinbrenner went on to suggest that how players perform in the postseason, a small sample that he called a “crapshoot,” can drastically alter the perception of whether money was well spent. After all, fans — especially those in the Bronx — understandably only care about the end result.
AdvertisementAdvertisementAdvertisementTo Steinbrenner’s point, the 2025 regular season would tell you that the Yankees, who went 94-68 with approximately 50.6 fWAR, had a more efficient payroll than the Dodgers, who finished 93-69 with roughly 49.8 fWAR.
The Bombers spent about $3.4 million per win and $6.3 million per fWAR, while Los Angeles spent about $4.46 million per win and $8.3 million per fWAR.
However, the Dodgers, bankrolled by Guggenheim Baseball Management and making hundreds of millions off its dominance of the Japanese market, have spent more efficiently than the Yankees (and Mets) over the last five years, as Wilytics recently detailed in a lengthy video breakdown.
Some bad contracts have contributed to the Yankees’ inefficiency, as they have cut several players despite owing them millions of dollars. Recent examples include DJ LeMahieu, Marcus Stroman Josh Donaldson and, going back a bit further, Jacoby Ellsbury and Alex Rodriguez.
AdvertisementAdvertisementAdvertisementLeMahieu, designated for assignment last summer, is owed $15 million in 2026. That counts toward the club’s CBT payroll, which is currently projected to be $278.1 million, per Cot’s.
The Yankees also have several ongoing, long-term, high-priced contracts, including those belonging to Giancarlo Stanton, Gerrit Cole, Max Fried, Carlos Rodón and Aaron Judge, who it should be noted is underpaid despite his team-high $40 million average annual salary.
Spending efficiency can apply to more than the CBT payroll, which covers the 40-man roster.
Steinbrenner proudly noted that “nobody spends more money, I don’t believe, on player development, scouting [and] performance science.” That’s tough to independently verify given the vagueness of the claim, lack of public information and a variation in lingo used by different organizations. But even if it is true, spending the most doesn’t mean spending the best.
AdvertisementAdvertisementAdvertisementFor example, the Yankees have burned millions of dollars on high-priced Latin American amateurs in recent years, prompting the departure of international scouting director Donny Rowland.
Baseball America, meanwhile, shows the Yankees have fluctuated in farm system rankings over the last 10 years, occasionally cracking the top 10 but falling below it more frequently. Such variation is to be expected given their annual status as contenders, win-now expectations that demand trading well-regarded prospects, pricey payrolls, lack of high draft picks and limited international pool money, but the Dodgers have operated under similar constraints.
They’ve maintained a top 10 farm system for the past decade.
“They do have tremendous resources, and they’ve gotten the job done,” Steinbrenner said, more focused on what L.A.’s major league team has accomplished. “That’s the big thing. They’ve played to their potential when they needed to.”
AdvertisementAdvertisementAdvertisementThe Yankees have not, and that’s going to matter to fans far more than subjective farm system rankings, dollars spent per WAR or the team’s overall payroll. No one is rooting for those things.
But more efficient spending would certainly help the Yankees in the long run – and could be achievable if young, cost-controlled players meet expectations – especially with the sport’s financial parameters potentially changing following the expiration of the Collective Bargaining Agreement next offseason.
For now, however, the Yankees still need to address their outfield, their pitching staff and their bench with the Winter Meetings approaching. That’s going to cost money, and not necessarily an efficient amount.
“We can talk before [Cashman] goes into the Winter Meetings about a range,” Steinbrenner said when asked if he’s willing to go over $300 million again, “but because it’s a fluid situation, that range can go bye-bye in two seconds if there’s a deal that arises that I feel would be very beneficial to some area of need that we have. “It’s hard to give you a number.”
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