Big Brown. If you were watching the Run for the Roses back in 2008, that name probably still rings a bell, and honestly, not just because he won. He was a monster on the track. When the 2008 Kentucky Derby winner crossed the wire at Churchill Downs, he didn't just win; he dominated. He won by nearly five lengths, coming out of the dreaded twenty-hole, which basically never happens. Most horses stuck on the far outside get cooked by the first turn. Not him.
But here’s the thing. The story of the 2008 Kentucky Derby winner is sort of a tragedy in two acts. Act one was the sheer, terrifying brilliance of a horse that looked like he might be the first Triple Crown winner since Affirmed in 1978. Act two? Well, that was the heartbreak of Eight Belles and the absolute confusion of the Belmont Stakes. If you want to understand modern horse racing, you have to look at Big Brown. He was the bridge between the old-school grit and the high-stakes, pharmaceutical-heavy era that the sport is still trying to figure out today.
The Freak from the Outside Post
Coming into the 134th Kentucky Derby, everyone knew Big Brown was fast, but there were massive question marks. He had only run three times before. Three. In the modern era, that’s not totally crazy, but in 2008, it felt like he was lacking the "bottom" or the stamina needed for a mile and a quarter. Plus, he had these recurring foot issues—quarter cracks—that kept his trainer, Rick Dutrow Jr., up at night.
Then the draw happened. Big Brown got post 20.
In the history of the Derby, winning from the outside is a statistical nightmare. You’re essentially running further than every other horse because you have to clear the field to get to the rail. Kent Desormeaux, the jockey, didn't care. When the gates opened, Big Brown just glided. He sat wide, moved like a ghost through the final turn, and then he just... left. He made good horses look like they were standing in wet concrete.
Watching it live, you felt like you were seeing a once-in-a-generation athlete. He became the first horse since Regret in 1915 to win the Derby with only three prior starts. He was an anomaly. A fast, brown, powerful anomaly.
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The Eight Belles Tragedy
We can't talk about the 2008 Kentucky Derby winner without talking about the shadow that fell over the track moments after the finish. Eight Belles, a gorgeous, gutsy filly, finished second. She ran the race of her life. But as she was slowing down past the finish line, she collapsed. She had broken both front ankles.
It was horrific.
While Big Brown’s owners, including the IEAH Stables crew, were celebrating in the winner's circle, the track vets were euthanizing Eight Belles right there on the dirt. It changed the vibe of the entire year. It sparked a massive national debate about the surface of Churchill Downs and the breeding of Thoroughbreds. People were asking: are we breeding these horses to be too fast for their own bones? Big Brown was the champion, but Eight Belles was the reason the evening news was talking about horse racing that night.
Why Big Brown was Different
What made Big Brown so "scary" to his competitors?
- The Stride: He had a massive, efficient reach that didn't seem to tire him out.
- Tactical Speed: He could sit anywhere. He didn't need the lead, but he could take it whenever he wanted.
- The Visuals: He looked like a statue. He was a physically imposing horse that intimidated other runners.
The Steroid Controversy and Rick Dutrow
If you’re looking for a "clean" hero story, this isn't it. Rick Dutrow Jr. was, and is, a polarizing figure in racing. He was incredibly vocal—some would say arrogant—about how good his horse was. He famously told the press that Big Brown was a "foregone conclusion" for the Triple Crown.
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But the real noise was about Winstrol.
Back in 2008, stanozolol (Winstrol) was actually legal in Kentucky and several other racing jurisdictions, provided it wasn't given too close to race day. Dutrow openly admitted to giving Big Brown monthly injections of the anabolic steroid. He didn't think it was a big deal because everyone was doing it, or so he claimed. But for the general public, it felt like the "BALCO" era had hit the racetrack. When Big Brown went on to smoke the field in the Preakness Stakes, the "steroid horse" narrative was all anyone could talk about. It’s a bit unfair to the horse—he was clearly talented—but it’s a permanent part of the 2008 Kentucky Derby winner's legacy.
The Belmont Mystery: What Actually Happened?
Then came the Belmont. The "Test of the Champion." 1.5 miles.
Big Brown was the 1-4 favorite. It was supposed to be a coronation. I remember the crowd was electric, waiting to see history. Instead, they saw one of the weirdest performances in sports history. Big Brown moved up, looked like he was going to make his move, and then... nothing. He just stopped. Desormeaux pulled him up before the finish line because the horse had nothing left. He finished last.
To this day, people argue about why.
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- The Quarter Crack: His hoof issues had flared up again during the weeks leading up to the race. Maybe he was just in pain?
- The Steroids: Dutrow had stopped the Winstrol treatments before the Belmont because of the intense public scrutiny. Some people swear the horse "deflated" without the PEDs.
- The Heat: It was a brutally hot day in New York, and Big Brown wasn't a fan of the temperature.
- The Shoe: There was a theory that he stepped on a shoe or hit a rail, but the replays don't really show a definitive "moment."
Da' Tara won the race at 38-1 odds. The Triple Crown dream died in the dirt of Elmont, New York. It was a bizarre, quiet end to a campaign that had started with so much noise.
Legacy and the Stud Career
So, what do we make of the 2008 Kentucky Derby winner now?
Big Brown went to stud at Three Chimneys Farm and eventually moved to New York. As a stallion, he was... okay. He wasn't a total bust, but he didn't rewrite the breed like Northern Dancer or Mr. Prospector. He sired some good ones, like Dortmund, who was a beast in his own right, but he never produced a horse that quite matched his own raw power.
His win in the Derby remains one of the most visually impressive performances in the last twenty-five years. If you watch the replay, pay attention to the 3/16ths pole. The way he shifts gears is something you just don't see often. He was a powerhouse who got caught in the middle of a shifting culture in horse racing.
Actionable Insights for Racing Fans
If you're looking back at the 2008 season to understand how to handicap today's races, here are a few takeaways that still apply:
- Watch the Post Position, but don't obsess: Big Brown proved that a truly superior horse can overcome a bad draw. If you see a "freak" at 10-1 odds just because they are in post 1 or 20, they might still be worth a look.
- The "Bottom" Matters: Even with the best talent, a horse with foot issues and limited starts is a risk in the 1.5-mile Belmont. The Derby is about speed and talent; the Belmont is about skeletal durability.
- Trainer Reputation: Always look at who is conditioning the horse. Rick Dutrow's career was filled with highs and legal lows. A trainer's "program" often tells you more about a horse's consistency than their last workout time does.
- Foot Health is Everything: If a horse has a history of quarter cracks (like Big Brown or even more recent stars), be very wary of them on hard, fast tracks. Those injuries linger and can ruin a Triple Crown bid in a heartbeat.
Big Brown wasn't perfect. He was complicated, controversial, and ultimately human—or the equine equivalent. He reminded us that in horse racing, there are no "foregone conclusions," no matter what the trainer says.
Check the bloodlines of current Derby contenders; you'll still see Big Brown's name pop up in the pedigrees of many New York-bred stakes winners. He’s still there, a reminder of that wild summer in 2008 when we thought we’d finally found our next great king.