The New York Yankees used to be the financial juggernaut in Major League Baseball-the team everyone loved to hate, especially if you weren’t from the Bronx. But those days are slipping further into the rearview mirror. If there was any lingering debate about which team now wears the league’s villain crown, Kyle Tucker’s decision to sign with the Los Angeles Dodgers just ended it.
No, the Yankees weren’t in on Tucker. Any whispers that they might’ve been were more about posturing-likely a move to nudge Cody Bellinger into taking their offer.
But that’s not the point. The real story here is what Tucker’s massive average annual value (AAV) deal says about where the Dodgers are financially-and where the Yankees might be falling behind.
The Dodgers’ Corporate Engine vs. the Yankees’ Family Business
The Dodgers, as flashy as their on-field product is, are just as formidable off the field. Mark Walter is the face of ownership, and Magic Johnson gives them star power, but the real muscle comes from Guggenheim Baseball Management-a deep-pocketed group backed by Guggenheim Investments. That’s not a family business; that’s corporate horsepower.
We’re seeing more of that across the league. The Toronto Blue Jays, for example, are owned by Rogers Communications, a Canadian media giant.
These ownership groups aren’t just wealthy-they’re structured to spend, invest, and scale. And in today’s MLB, that’s becoming a competitive advantage.
The Yankees, meanwhile, remain largely a family-run operation. Hal Steinbrenner is at the helm, but he’s not operating with the same kind of financial firepower as some of his peers.
As of last August, Steinbrenner didn’t even crack the top 12 richest owners in the league. His estimated net worth-around $1.5 billion-is dwarfed by Steve Cohen’s $21.3 billion fortune across town in Queens.
For years, the Yankees leaned on the strength of their brand and their stake in the YES Network to fund their spending. And for a while, that worked.
But the game is changing. Teams are bringing in outside investors and reinvesting that capital directly into the roster.
That’s how you land a player like Kyle Tucker.
Where the Yankees Go From Here
Let’s be clear: Steinbrenner isn’t selling the Yankees. The team is still a revenue machine, and beyond that, it’s a family heirloom. But if the Yankees want to keep pace with the Dodgers, Mets, and others operating in this new financial landscape, Steinbrenner may need to evolve his approach.
One option? Bringing in minority investors.
It’s a move we’ve seen across sports-selling off stakes without giving up control, all to raise capital and stay competitive. Because the old-school approach of stretching contracts to lower the AAV hit?
That’s quickly becoming outdated. In an era of deferred money and aggressive short-term deals, teams need liquidity now and in the years to come.
Right now, the Yankees are at a crossroads. They can either adapt to the modern financial model or risk falling further behind the teams that already have.
The “Evil Empire” nickname once struck fear across the league. But if the Yankees don’t recalibrate, that moniker might soon feel more like a piece of baseball nostalgia than a reflection of their current standing.