Chip Woolley had a broken leg and a beat-up Ford F-150. He drove over 1,200 miles from New Mexico to Kentucky with a brown gelding in a hitched-on trailer, pulling into Churchill Downs like he was looking for a local rodeo rather than the most prestigious horse race on the planet. Nobody cared. Why would they? The horse, Mine That Bird, was a small, unassuming son of Birdstone who had been finishing fourth in races at Sunland Park. When the gates opened on that rainy Saturday in 2009, the betting world had basically written him off as a "clutter" horse—someone there to fill the field while the real titans like I Want Revenge or Pioneerof the Nile did the heavy lifting.
Then the mud started flying.
He won. It wasn't just a win; it was a demolition. Mine That Bird didn't just beat the best three-year-olds in training; he embarrassed them by 6¾ lengths, the largest margin of victory in over sixty years. If you look at the grainy replay, you can actually hear the announcer, Tom Durkin, lose his mind because he literally didn't see the horse coming until he was already passing the leaders. It’s the kind of story that makes people buy a lottery ticket. It’s also a story about physics, rail-skimming, and a jockey named Calvin Borel who had nerves made of literal steel.
Why Mine That Bird Was the Ultimate Statistical Anomaly
In horse racing, we talk about "speed figures" and "trip notes" constantly. Looking back at the data from the 2009 Derby, Mine That Bird shouldn't have been within ten lengths of the winner. He had won the Grey Stakes as a two-year-old in Canada, sure, but his form leading into the Triple Crown was, frankly, abysmal. He finished second in the Borderland Derby and fourth in the Sunland Derby. Most experts thought he was a synthetic-track specialist who would choke on the deep, sloppy dirt of Louisville.
Betting $2 on him netted you $103.20.
The sheer scale of the upset is hard to wrap your head around unless you understand the "Calvin Borel factor." Borel, nicknamed "Bo-Rail," had a signature move. Most jockeys stay wide to avoid the kickback—that nasty, heavy mud hitting the horse's face. Not Calvin. He ducked Mine That Bird so close to the inside rail that the horse's left stirrup was practically scraping the wood. While the rest of the field was laboring through the sludge in the middle of the track, Mine That Bird found a "dryer" path on the inside, saving dozens of feet in distance.
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He went from dead last—and I mean way back, at least 20 lengths off the lead—to first in about thirty seconds. It was a teleportation act.
The Myth of the "Fluke"
People call this horse a fluke all the time. Is it a fluke if you repeat the performance? After the Derby, Mine That Bird went to the Preakness Stakes. Everyone assumed he’d revert to form and finish middle of the pack. Instead, he put in another massive run, finishing second to the legendary filly Rachel Alexandra. He followed that up with a gritty third in the Belmont Stakes. That Triple Crown run—1st, 2nd, 3rd—is something very few "great" horses ever actually achieve.
He wasn't a one-hit wonder. He was a distance specialist who thrived on chaos.
The horse’s career ended with earnings over $2.2 million, which is staggering for a gelding that was once sold for just $9,500 as a yearling. Most owners spend millions trying to find a Derby winner and end up with nothing but high stable bills and disappointment. Mark Allen and Dr. Leonard Blach, the owners who took a chance on the "bird," found the ultimate diamond in the rough.
The Cultural Impact: From the Track to the Big Screen
The story was so ridiculous that Hollywood actually made a movie about it called 50 to 1. It captures that grimy, New-Mexico-cowboy aesthetic that Woolley brought to the hallowed grounds of Churchill Downs. Woolley, with his black cowboy hat and crutches, became an overnight folk hero. He represented the "little guy" in a sport that is increasingly dominated by billionaires and massive bloodstock syndicates.
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Honestly, the sport needs more of that.
Nowadays, the Kentucky Derby is often won by horses that cost $500,000 or more at the Keeneland sales. When a horse like Mine That Bird comes along, it reminds everyone that at the end of the day, these are animals, not machines. You can't always calculate heart or the ability to handle a sloppy track.
What You Can Learn From the 2009 Derby
If you’re a bettor or just a fan of the sport, there are real takeaways from this specific race that still apply today:
- Watch the track bias: On rainy days at Churchill Downs, the rail often becomes a "highway." Borel knew this; the other jockeys ignored it.
- Don't ignore the New Mexico circuit: While it isn't Saratoga or Santa Anita, horses coming out of Sunland Park often have high fitness levels due to the climate.
- The "Birdstone" bloodline: Birdstone sired two classic winners in his first two crops (Mine That Bird and Summer Bird). It was a brief but explosive period of stamina-heavy production that changed how breeders looked at "staying" power.
Where is Mine That Bird Now?
Fortunately, this story has a happy ending. Many racehorses face uncertain futures once their speed fades, but Mine That Bird is living the dream. He spent several years as a "pony" at Mark Allen's Double Eagle Ranch, essentially acting as a calm mentor for younger, nervous racehorses. It’s a bit poetic—the ultimate underdog teaching the next generation how to behave.
He eventually moved to the Kentucky Derby Museum at Churchill Downs.
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He stayed there as a resident for a while, letting fans see the diminutive horse that conquered the giants. As of the mid-2020s, he has returned to New Mexico to enjoy his retirement in the desert sun. He’s healthy, well-fed, and probably has no idea he caused one of the biggest financial swings in the history of the American sportsbook.
The legacy of Mine That Bird isn't just about the money won or the trophies on the shelf. It’s about the reality that in horse racing, the form book is just a suggestion. Sometimes, the smallest horse with the cheapest price tag is the one who finds the gap on the rail and changes everything.
Actionable Next Steps for Fans and Bettors
If you want to dive deeper into the mechanics of why this happened, start by watching the 2009 Derby overhead cam (not the broadcast view). You’ll see Borel’s pathing in a way the TV cameras missed. For those looking to spot the next big upset, keep an eye on "closers" with high stamina ratings when the track condition is listed as "Sloppy" or "Muddy."
Don't just look at the last race's finishing position; look at the "troubled trip" notes. Mine That Bird had plenty of excuses in his losses, but the betting public only saw the "4" next to his name. The real value is always in the details that the casual observer overlooks. Pay attention to the jockeys who aren't afraid to get dirty on the rail, and never, ever discount a horse just because the trainer arrived in a beat-up truck.