I Spent a Season Following John Stewart in Horse Racing — Here’s How It Felt

I didn’t plan this. I just wanted a fun fall at the track. Then John Stewart showed up like a storm, and, honestly, I got hooked on the whole ride.

You know what? I like bold folks who try new stuff. That’s him. Loud, yes. But also clear. And weirdly open for this sport. I actually laid the whole journey out in a longer journal on PDV Racing, and you can browse it race-day by race-day here.

What I Actually Did

  • I watched the Keeneland September Yearling Sale in 2023. I sat in the back ring with a pen and a very bad coffee.
  • I went to the Fasig-Tipton November Sale. Long night. Big prices. Big buzz. (You can see the official ledger of that night here).
  • I kept up with his posts and interviews. He talked safety and shared what he could about vet checks. That mattered to me as a fan and a bettor.

So this isn’t armchair talk. I was there for some of the key moments.

The Moment That Hooked Me

At Fasig-Tipton last November, the ring got tight and quiet. The mare Goodnight Olive came in. Grade 1 class. You could feel the air change. The bids jumped, fast. Then the hammer fell at $6 million. Buyer: John Stewart’s Resolute. People let out this little gasp. I did too. It felt like someone had just flipped the lights on in the room.

That was real. I was standing under the board with hip numbers all over my catalog. My hands shook a bit. Sales do that to you sometimes.

The Spending Spree (And Why It Mattered)

Back in September at Keeneland, he bought yearlings like a kid with a cart at Costco. Over $15 million in a week, by my notes and the sale reports. Earlier at Saratoga, he even dropped $3 million on an Into Mischief colt—Resolute’s headline buy at that meet (full story). I watched his paddle go up again. And again. It wasn’t just the money, though. It was the message: I’m here, and I’m going big.

Now, I’ve seen folks splash cash and fade. This felt different. He kept showing up. He kept talking about the sport, not just the trophies.

The Part That Surprised Me: Transparency

Here’s the thing. After a rough summer for racing, trust felt thin. So when he said he’d share vet records around big days, I leaned in. That’s not normal in this game. It’s also messy. But it made me feel seen as a fan who wagers and worries. Safety talk isn’t flashy. It’s needed.

Did it fix everything? No. But it was a step. A clear one.

What It’s Like on a Race Day

This part’s simple. When one of his horses runs, the buzz gets louder. Folks on the rail chat about pedigrees and prices. The paddock feels busy. You hear, “That’s one of the Stewart buys,” like it’s a weather update.

I like that. It brings casual fans in. Even my neighbor, who only bets exactas with birthday numbers, asked me, “Is that the new guy?” Yep. And he’s fun to follow.

The Good Stuff

  • Energy: He makes the room feel alive. Sales. Races. Even the dead time between.
  • Clarity: He says what he’s doing and why. In plain words. I respect that.
  • Investment: He spends, sure. But he also engages. It’s not just a name on a program.
  • Fan-facing: When an owner talks to bettors like adults, I notice.

The Not-So-Good (Because Nothing’s Perfect)

  • It’s loud: Some old-school folks don’t love the noise. I get it. Tradition runs deep here.
  • It’s early: Yearlings need time. Not every big buy turns into a star. Patience is part of the price.
  • Big swings: High bids can feel showy. It sets a bar, and the bar fights back.

I felt both ways at times. I liked the spark. I also winced once or twice. That’s normal.

For a contrast in tone, check out my earlier season shadowing the scrappy Bassett Racing outfit — dirt, dents and all — right here.

A Small Digression on Culture

Horse racing can be clubby. Rules you don’t see. Nods you don’t get. A guy like this walks in, flips a chair, and says, “Let’s talk.” Is that jarring? Yep. But it can be healthy. Change needs friction. The sport needs new fans—or at least fewer doors. If you think the mainstream track feels insular, try dipping a toe into Charlotte's clandestine scene; I went once and wrote an honest take over here.

I grew up around barns that smelled like pine shavings and worry. I want kids to feel welcome at the rail. Owners who talk openly help.

Who This Will Appeal To

  • New fans who like a clear story to follow
  • Bettors who care about horse health and open info
  • Sales nerds (like me) who mark hips and track results
  • Folks who want the sport to push forward, not stand still

If you want quiet, this won’t be your cup of tea. And that’s okay.

Quick Tips If You Want To Follow Along

  • Watch the big sales live streams. Listen for his name. Keep a notebook. It helps.
  • On race days, check entries and morning works. See which purchases show up and how they move.
  • Don’t chase hype at the windows. Let the form guide you. Price matters more than buzz.

For extra stats, entry alerts, and a clear look at upcoming sales trends, I keep a tab open to PDV Racing because their dashboard makes tracking stables like Stewart’s Resolute feel almost effortless.

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My Verdict

John Stewart makes horse racing feel loud, fast, and oddly honest. Not everything lands. Some days the show is the show. But the sport feels more awake when he’s in the mix.

Would I keep following his stable? Yes. Would I trust every hot tip? No. I’ll still use my own notes. But I’ll also bring a little extra cash for a fun exacta when one of his big buys walks into the paddock with that look. You know the one. Ears up. Coat like glass.

I walked into this fall a little tired of the same old tune. I left feeling hopeful. That’s worth a lot.