Who Wants to Be a Billionaire?

Woke up this morning with a question on my mind: What would be fun about being a Major League Baseball owner?

Let’s make three assumptions at the start.

Assumption 1: You’re a billionaire. This doesn’t have to be true. I’m looking at a chart here that says several baseball owners — Bob Castellini in Cincinnati, Bruce Sherman with the Marlins, Mark Attanasio in Milwaukee, Richard Monfort in Colorado and Stuart Sternberg in Tampa Bay — are not official billionaires. But for our purposes, yeah, it’s important that you’re a billionaire.

Assumption 2: You’re a big baseball fan. This obviously doesn’t have to be true, there have always been owners who are meh on baseball and some who don’t seem to like the sport at all. Their reasons for owning a team are more business-related, civic-related, politically motivated, and I’m uninterested in that. What is on my mind is: What would be FUN about being a baseball owner. That other stuff doesn’t meet my definition of the word “Fun.”

Assumption 3: You aren’t buying the team for attention. I’ll be honest: I don’t know a single thing about most billionaires in this country. Sure, we all know the top dogs, the Elon Musks, the Bill Gates, the Jeff Bezoses, the Michael Bloombergs, the Mark Zuckerbergs, the “Succession” family, but go down the list to those making, like $10 or $15 or $20 billion, and I have no idea who these people are … unless they own a sports team.

I’m looking now at, say, Nos. 46 to 58 on the Fortune 400 list.

No. 46: George Kaiser. No idea. I guess he’s in oil or something. I’m seeing now he’s a silent minority owner of the Oklahoma City Thunder … he really should speak up.

No. 47: Jan Koum. No idea. I guess he co-founded What’s App or something. Says here he doesn’t want to be called an entrepreneur. Fascinating.

No. 48 (tied): Jensen Huang. No idea. I guess he’s into semiconductors. I don’t even know what those are.

No. 48 (tied): Stan Kroenke. Oh, yeah, I know Stan Kroenke, he’s the son of a gun who moved the Rams from St. Louis. I know all about him — know that I don’t like him for any number of reasons, even though his full name is Enos Stan Kroenke, and he was named after Enos Slaughter and Stan Musial.

So, yeah, becoming a sports owner will introduce you to many millions of people who don’t have any idea who you area. It’s quite striking when you get down to those paupers making somewhere in the $5 billion range.

211. Ron Baron. No.

212. Robert Bass. No.

213. Dan Snyder. Oh, yeah, I know all about Snyder, that jerk.

214. Charles Dolan and family. Oh yeah, I know all about Dolan, that jerk.

215. Charles Ergen. No.

216. The Johnson family of Wisconsin. No.

217. Robert Rowling. No.

The point is: I can only ASSUME I would dislike the other billionaires. But I KNOW I dislike the billionaire sports team owners.

So, yeah, you might buy a sports team so people will know you (and inevitably dislike you) but that’s not what we’re talking about here.

Bogaerts is the Padres’ latest expensive acquisition. (Winslow Townson/Getty Images)

What are we talking about, then? Well, it seems to me that what would be FUN about owning a baseball team is that you would get to play in the greatest fantasy baseball league on earth. You would be competing against all these other billionaire competition monsters in the most clear-cut way. Every day there’s a winner. Every day there’s a loser. At the end of the season, there are division champions. At the end of the playoffs, there’s a World Series champion and a giant parade.

There’s no place to hide, no excuses that matter, no defense for ineptitude.

I think I woke up thinking about this because of two owners in particular — Boston Red Sox owner John Henry (net worth $2.6 billion) and San Diego Padres owner Peter Seidler (net worth $3 billion).

I obviously don’t know either of them, but they both seem to come by their baseball love honestly. John Henry grew up a big Cardinals fan, and before he became a bajillionaire by establishing a firm that, according to Wikipedia, makes “mechanical non-discretionary trading decisions in response to systematic determinations of reversals in each market’s direction,” he owned a minor league baseball team and helped start the Senior Professional Baseball Association. He also was involved in several other teams before the Red Sox, including the Miami Marlins and the Colorado Rockies.

Henry, it has been said, even likes playing baseball simulation games.

Seidler, meanwhile, is the grandson of the Hall of Fame Dodgers owner Walter O’Malley. He made his billions by founding some private equity firm, but from what I’ve read, baseball has always been on his mind.

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OK, so you have two billionaires, both baseball lovers, both have shown in the past that they want to win.

But … here’s the thing. John Henry HAS won. He’s won A LOT. His Red Sox broke the curse and won the World Series in 2004. Then they won it again in 2007. Then they won it again in 2013. Then they won it AGAIN in 2018.

And, suddenly, after that, winning didn’t seem quite as urgent in Boston. They let Mookie Betts go. They made a big deal about getting under the luxury tax threshold. They’ve been roughly a .500 team since 2019, and their farm system is generally rated as OK but not exceptional, and on Wednesday they got outbid for their superstar shortstop Xander Bogaerts — I saw one report that they didn’t even finish in the top three in the Bogaerts race.

This, even though Bogaerts reportedly really wanted to stay in Boston.

Then you look to San Diego and Peter Seidler — he’s never won it all, and the Padres have never won, and he’s spending money like he’s in some “Brewster’s Millions” plot. Before this offseason even began, Seidler and the Padres had already invested $300 million in Manny Machado and $340 million in Fernando Tatis Jr. and $126 million in Yu Darvish and $100 million in Joe Musgrove, and whatever millions they will need to pay Juan Soto for 2023.

Then word came down that the Padres had offered more than $400 million to steal Aaron Judge away from the Yankees.

And while we were letting that sink in, the Padres went out and got Bogaerts, spending $280 million for 11 years.

Does it make financial sense? Probably not. Does it make long-term baseball sense? Probably not. Bogaerts is already 30. Does it make the Padres favorites to win the World Series? Probably not. The pennant? Probably not. The Dodgers are still the Dodgers. The Braves and Mets and Cardinals are all really good.

We don’t even know for sure how well this move will work short -term. It must be said: Bogaerts hit A LOT better at Fenway Park than he did on the road, and Petco Park can be a batter’s nightmare, and Bogaerts has been up and down defensively and his signing means moving Tatis Jr. to centerfield, where, who knows?

But let’s say this: The Padres are SUPER INTERESTING.

And it comes full circle: What would be fun about being a baseball owner? Well, making your team SUPER INTERESTING is fun! Signing Xander Bogaerts is fun! Bidding on Aaron Judge is fun! Building a team of superstars would be fun. Making everyone across baseball go “Wow!” is fun! Ticking off all the other owners is fun! Making every push to finally win that World Series is fun!

Sure, all of that costs a lot of money. But I’m a billionaire, man! What’s even the point of being a billionaire if I can’t spend some cash and make Xander Bogaerts my shortstop?