It is absolutely fair to wonder sometimes how much Hal Steinbrenner really loves baseball, or loves being Boss (2.0) Steinbrenner of the Yankees. He often seems uncomfortable — and occasionally downright reluctant — being successor to his late father as the principal owner of the Yankees. But the idea that Steinbrenner the Son somehow doesn’t spend enough on his team happens to be nuts. It’s as tired a narrative as the one about Yankee fans being spoiled.
No, the problem isn’t that he doesn’t spend enough, or that he’s now been passed by Uncle Steve Cohen, somebody else who must be wondering how much is enough. Maybe the real problem is the way Yankee money — with Hal in the big chair — has been spent on one Yankee team after another not good enough to win it all.
Here is a fact of Major League Baseball, one that obviously might change if the Dodgers continue to win the World Series every year:
Most money doesn’t always win.
Oh, sometimes it does, the Dodgers just proved that. But here are the last 10 teams to win the Series, and where they ranked in payroll when they did:
2016 Cubs, 3rd in payroll.
2017 Astros, 8th.
2018 Red Sox, 1st.
2019 Nationals, 5th.
2020 Dodgers, 1st (in a shortened COVID season.)
2021 Braves, 11th.
2022 Astros, 7th.
2023 Rangers, 7th.
2024 Dodgers, 3rd.
2025 Dodgers, 1st.
Something else to know about Hal Steinbrenner? In the time he has been the boss, effectively since 2008, the Yankees have had the highest payroll in baseball seven times, the second-highest six times, the third-highest twice. And have played in two World Series and won one.
So, for fans thinking that Hal isn’t engaged fully enough in an arms race with the Dodgers — and we’re not talking about pitching arms — a fair question might be this:
How much more does he need to spend after what he’s spent already on all those teams good but not good enough?
Steinbrenner continues to hammer home the point that a $300 million payroll ought to be enough. And guess what? He happens to be right about that. Right now, this minute, he employs three players who once signed $300 million contracts: Aaron Judge, Giancarlo Stanton, Gerrit Cole. He has another pitcher, Max Fried, working on a long-term, $218 million contract.
Cole obviously wasn’t on the field this season, having undergone Tommy John surgery in the spring. But with that most recent $300 million Yankee payroll — around $50 million less than what Cohen spent on baseball players in 2025 — Steinbrenner watched his team struggle to make it past the Red Sox (who spent $100 million less on players than the Yankees) in the wild card round. Then he watched his guys get rolled by the Blue Jays in a division series that was on its way to being a sweep before the Yankees came back from 1-6 down in Game 3.
Steinbrenner was asked the other day if it’s still realistic for him to basically think that every year is Canyon of Heroes or bust for the Yankees.
“I certainly thought it was last year,” he said. “And now we begin the work of next year. But I absolutely went into the playoffs believing we could win a championship.”
He had a right. The Yankees had just played in their first Series in 15 years the previous October. They had come out of the regular season — and despite a miserable stretch in the middle of the season — tied with the Blue Jays for the most wins in the American League.
Then we saw what we saw against the Blue Jays when, according to the owner, his team didn’t “play up to its potential.” Once again, the Yankees were good but not good enough. It’s not much of a marketing slogan. But it’s who they are, when they spend the most or when they don’t. The only consolation for Steinbrenner is that he got a lot more of a bang for his buck than Cohen did with a Mets team that didn’t even make the postseason and will go down as one of the most embarrassing financial failures we’ve ever seen in all professional sports, not just baseball.
But the Mets are not the Yankees and Steinbrenner is the owner in the news this week because he is the one who faced the media, and had to answer more questions about money.
By the way? Go ask Red Sox fans if they think their owner is spending enough. Go ask Cubs fans. And in a year when the Yankees had the third-highest payroll, the Blue Jays were a couple of slots behind them in fifth. The Jays ultimately spent around $50 million less than Steinbrenner’s team did on baseball players, and we all saw how close they came to beating the Dodgers in the Series, going home to Toronto ahead three games to two, and having all those late-game chances in Game 7 of the best Series we might ever see.
None of that mattered on Tuesday, because Steinbrenner got jumped almost as soon as the words about trying to drop payroll even a little bit were out of his mouth; and even though he almost immediately added that it wasn’t likely to happen.
One more thing about Hal Steinbrenner: Do the people who think he isn’t willing to go far enough to money-whip the competition think he offered Juan Soto more than $700 million last winter just to show what a good sport he is?
Yankee fans don’t have to love him. They can keep falling back on the tired refrain about his father: What Would George Do? There’s an old line we’ve all heard about how money doesn’t buy happiness, but will certainly finance an exhaustive search. Hal is still searching, after all this time in the big chair and all the resources he has given his general manager. But if you think he’s the biggest reason the Yankees have won one World Series in the last 25 years, think again.
