So picture this: It’s a crisp October evening in 2016, and my buddy Greg—a guy who once cried during a Marlins game—is clutching his rally towel like it’s a life raft. The Cubs just won the World Series, and he’s sobbing into his beer, whispering, “I don’t even know who to thank for this.” I laughed and said, “Probably the guy who writes the payroll checks, Greg.” And that, my friends, is how we stumbled into the bizarre, sticky web of Cubs ownership.
Today, the Chicago Cubs are owned by the Ricketts family, and they’re about as close to a royal dynasty as you can get in baseball. It all started in 2009, when Tom Ricketts—a mild-mannered investment banker with a great hairline—led a group to buy the team for a cool $845 million. Yes, you read that right. Eight-hundred-forty-five-million. For a ballpark and a bunch of guys hitting things with sticks.
But here’s the twist: Tom isn’t the only Ricketts in the ownership box. The family tree is practically a sitcom cast. You’ve got Tom, the public face and board chairman; his brother Pete, a former baseball exec who now helps with strategy; sister Laura, who runs the foundation; and sister Todd—yes, Todd, with a “d”—who handles community relations. (Side note: Imagine being named Todd if you’re a woman. My cousin Brenda is still mad about being called “Brent” in third grade, so I feel that.)
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The Backstory: How a Banking Family Bought a Ballclub
The Ricketts didn’t just stumble into Wrigley Field with a suitcase of cash. Their father, Joe Ricketts, founded TD Ameritrade in the 1970s and turned it into a brokerage behemoth. So when Joe’s kids wanted to buy a baseball team, the family wallet was basically a black hole of money. But here’s the irony: Joe himself isn’t part of the ownership group. He’s a reclusive libertarian who once funded a super PAC that tried to “brand” mosquitoes. (I’m not making that up. Google it. I’ll wait.)
So the kids pooled their inheritance—and a lot of borrowed cash—to outbid Mark Cuban, who famously called Wrigley Field “a dump.” Cuban wanted to tear it down and build a parking lot with a Jumbotron. The Ricketts, to their credit, said, “Let’s keep the ivy and the hand-operated scoreboard, thanks.” Smart move, because tradition sells hot dogs.
The Hidden Players: Who Else Has a Piece of the Pie?
Now, don’t think the Ricketts own 100% of the Cubs. They’re the majority owners, sure, but there are minority stakeholders—like a secret club of billionaires who meet in a hidden room under the bleachers. (I made that last part up, but probably true, right?) Notable minority investors include Dan Sileo, a former NFL player, and a bunch of private equity types who probably write “synergy” in their sleep.
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But here’s the funny part: The Cubs are legally owned by something called the “Cubs Baseball Enterprise”, which technically includes Wrigley Field and all its dirt. When the Ricketts bought the team, they also got the rights to the “Friendly Confines” vibes, the 7th inning stretch, and the ghost of Harry Caray. (Okay, that last one isn’t a line item, but it should be.)
The Big Question: Why Do We Care So Much?
You might be thinking, “Why does it matter who signs the checks? I just want a hot dog and a double play.” And you’re not wrong. But ownership matters because it dictates everything—from ticket prices to whether they sign a pitcher who throws 99 mph or a guy who’s just really nice in the clubhouse.
Look at the Ricketts’ record: They’ve spent $500 million renovating Wrigley Field, built a hotel across the street, and even dug up the warning track to install better drainage. But they’ve also been stingy with player payroll in lean years—like when they let Kris Bryant walk in 2021. Fans booed. I booed. My cat booed and he doesn’t know what a baseball is.
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Still, the Ricketts family is the stable hand at the wheel. They’ve survived a 2020 pandemic, a cheating scandal involving a sign-stealing Astros team (not their fault, but still), and the eternal curse of the goat. Actually, the goat curse was lifted in 2016, but I’m pretty sure there’s a new curse involving a raccoon that lives in the right-field wall now.
The Final Pitch: It’s a Family Affair (Sort Of)
So who owns the Cubs? It’s the Ricketts family, led by Tom, with a posse of siblings and a few silent billionaires in the background. They’re not perfect—they’ve made some head-scratching trades and raised beer prices higher than a Wrigley rooftop—but they’re the folks we’ve got.
And honestly, could you imagine owning a baseball team? You’d have to argue with 40,000 fans every night, explain why you didn’t hire a better relief pitcher, and pay for all that bubble gum. The Ricketts do it so we don’t have to. The least we can do is buy a foam finger and yell “Let’s go, Cubbies!” until our laryngitis insurance kicks in.
Now if you’ll excuse me, I have to go check if my neighbor Greg is still crying over that 2016 game. He probably is. Some wounds never heal—but at least the ownership is clear. Go Cubs. And maybe fix the bathroom sinks in Section 434, Tom. Just a thought.