WATCH: Ben Kawaller Tries to Ruin the Kentucky Derby

WATCH: Ben Kawaller Tries to Ruin the Kentucky Derby

Our correspondent tried to foment class war at the country’s most prestigious horse race. But it’s hard to bring a rich man down.

I was raised in a wealthy, liberal area of Brooklyn, which means that I did not grow up worrying about money, and that I atone for this sin by feeling terrible about it. I come from the milieu that produced the iconic image of Alexandria Ocasio-Cortez at the 2021 Met Gala wearing a designer dress that demanded “Tax the Rich.” Like the Democratic congresswoman, I wish to enjoy the finer things in life—and for that I am very, very sorry. 

So leave it to me, when I descended upon the Kentucky Derby earlier this month, to start asking everyone about wealth inequality. I wanted to know if anyone in this ostentatious and largely Republican crowd thought there was anything to the idea that America is anything less than a pure meritocracy.

My routine was to sidle up to some unsuspecting partygoer, make inoffensive small talk about our outfits, and then watch them edge steadily away from me as soon as I started feeling them out on tax policy. I soon discovered that politics at a horse race is about as welcome as flatulence at an orgy. 

Not that that stopped me from making everyone uncomfortable, even those who were nice to me. One man in the famed Millionaires Row seats guided me through placing a bet on a racehorse, only to be rewarded with: “Thank you. Now, do you come from money?” He elected not to answer. 

Not everyone was so reticent. I spoke to people from a range of backgrounds, including not just businessmen who’d inherited their fathers’ companies but people who’d grown up in poverty and achieved the American Dream. Their response generally went: If they could do it, can’t anyone?

I wanted to direct them to the neighborhood immediately surrounding Churchill Downs, where working-class residents sell food on the sidewalk or rent their driveways for parking space. Surprisingly, though, none of the six or seven working-class people I spoke with seemed all that interested in resenting the wealthy. 

I asked one woman who was selling dollar hot dogs in her front yard if she thinks a lot about wealth inequality. “I really don’t,” she told me. “I just live by my means.” I asked another food seller if she had any resentment toward rich people: “Nah, I just want them to come over here and spend some of that rich money with me.” Another woman, thrilled to be working as a server to the millionaires, seemed positively scandalized by my efforts to get her to indulge any class resentment. “We’re not going to talk about that,” she told me. “We’re going to talk about my joy. . . and about how I want to progress.”

Or, as one drunk college-aged girl I met in the infield put it, “Why are we focusing on the negative?” 

I asked her if she thought anyone so focused on the negative might have a point about. . . anything. She launched into a tirade, saying they just complain, “We don’t have this, we don’t have this, they have this, this is annoying.”

She said she has a different view. “We are living and we are breathing. That is a blessing. Enjoy it.” 

I asked this girl if she knew anyone in the pricier seats. She told me her parents were in Millionaires Row.

If you like what you see, watch Ben’s previous dispatch: “Is America Racist? Reggae Fans Aren’t So Sure.” Click here to learn more about “Ben Meets America!” 

Become a Free Press subscriber today:

Subscribe now

our Comments

Use common sense here: disagree, debate, but don't be a .

the fp logo
comment bg

Welcome to The FP Community!

Our comments are an editorial product for our readers to have smart, thoughtful conversations and debates — the sort we need more of in America today. The sort of debate we love.   

We have standards in our comments section just as we do in our journalism. If you’re being a jerk, we might delete that one. And if you’re being a jerk for a long time, we might remove you from the comments section. 

Common Sense was our original name, so please use some when posting. Here are some guidelines:

  • We have a simple rule for all Free Press staff: act online the way you act in real life. We think that’s a good rule for everyone.
  • We drop an occasional F-bomb ourselves, but try to keep your profanities in check. We’re proud to have Free Press readers of every age, and we want to model good behavior for them. (Hello to Intern Julia!)
  • Speaking of obscenities, don’t hurl them at each other. Harassment, threats, and derogatory comments that derail productive conversation are a hard no.
  • Criticizing and wrestling with what you read here is great. Our rule of thumb is that smart people debate ideas, dumb people debate identity. So keep it classy. 
  • Don’t spam, solicit, or advertise here. Submit your recommendations to if you really think our audience needs to hear about it.
Close Guidelines