When the news broke that Tom Dundon, a Texas-born billionaire, is leading the group buying the Portland Trail Blazers, my first instinctual reaction was the same as other sports fans: curiosity.

Okay, it was good that the Blazers aren’t moving to another market. Houston sports fans know very well the loss of community identity and pride when a pro sports team is moved out of town. Only the worst among us would wish that on another fanbase.

So there was a sense of relief that a new owner is willing to take on the challenge of a dated arena and that Portland, one of the NBA’s most loyal markets, will keep its team.

On the surface, this looks like something worth celebrating. A Texan at the center of a major NBA deal, helping preserve the legacy of a franchise that means the world to its city. That’s a story I want to root for.

Taking the ‘Bad’ with the ‘Good’?

But then comes the baggage.

Dundon’s fortune is tied in part to subprime auto lending — a business sector that has left countless families financially wrecked. He was also connected to the failed Alliance of American Football, which ended in bankruptcy and lawsuits. Even though some people, including Mark Cuban, vouch for his love of the game and his willingness to invest, it’s hard to ignore the pattern of questionable or failed ventures.

And that leaves me wrestling with a dilemma that feels awfully familiar: can you separate the art from the artist?

We ask that question all the time about entertainers who make music or films that we love, while their personal behavior or past actions cast a shadow over the work. Here, the “art” is the stewardship of a beloved NBA franchise. The “artist” is a businessman whose methods have sometimes drawn criticism.

From a Texas perspective, there’s another layer. Part of me feels instinctive pride when someone with roots here rises to prominence on the national sports stage. But what does it mean to “claim” that person when their fortune may have come, at least partly, at the expense of everyday people struggling to make ends meet?

Proximity-Based Reactions: ‘How Does This Impact Me?’

For Portland fans, the calculation may be different. If Dundon keeps the team in town, invests in a new arena, and builds a winner, maybe that’s enough. After all, fans usually judge owners by the health of the franchise, not the fine print of their business portfolios.

And Dundon isn’t the only one raising this tension.

Steve Ballmer, the billionaire owner of the Los Angeles Clippers, is widely seen as a socially responsible leader and a net positive for the NBA. But even Ballmer is now facing accusations of circumventing the salary cap in order to keep Kawhi Leonard in Los Angeles.

For many fans, it’s disorienting: here’s an owner who is generally admired, who has poured resources into the team and into community projects, and yet he’s under scrutiny for playing fast and loose with the rules.

Again, it raises the same question — can you separate the good an owner does for the franchise and community from the questionable ways they go about it?

Consistency Matters (Ours, not Theirs)

And that’s where I have to check myself. If I’m going to wrestle with the baggage that comes with Tom Dundon, I also need to be honest enough to wrestle with it when it’s Steve Ballmer.

I can’t love what one of these guys is doing and hate what the other is doing, just because one of them seems more likable or easier to root for.

Consistency matters. If the “art vs. artist” dilemma applies to one, it applies to both.

So, maybe that’s just the deal we accept when it comes to billionaire owners. We cheer the good they’re doing in the moment — keeping a team in town, building an arena, making the franchise competitive — but we also live with the knowledge that their history complicates the celebration.

The real question is: does that tension keep us honest, or does it quietly sweep everything under the rug and constantly talking out of both sides of our mouth?