In the third instalment of his series celebrating the 150th anniversary of America’s greatest race, Steve Dennis recalls one of the most unlikely outcomes in a storied history
If you want to get ahead, get a hat.
Men used invariably to wear hats. Newsreels and old photographs tell the story. Now hardly anyone wears a hat; baseball caps don’t count. Nevertheless, deep in the modern mythology of the Kentucky Derby there is a hat, a big black cowboy hat, an endu
ring emblem of one of the most unlikely winners of the race in its long history.
The man in the black cowboy hat was Bennie ‘Chip’ Woolley, a former bareback rodeo rider who by the time the sun had set on Louisville on the first Saturday in May had trained two winners in 2009.
The first was a two-furlong maiden at his local track, Sunland Park in New Mexico. The second was the Kentucky Derby.
That, though, was still one more victory than his horse had managed. Mine That Bird was Canadian champion two-year-old colt the previous year, but had been beaten in both his starts in stakes grade at Sunland Park that spring, his only races for Woolley.
Nowadays, Mine That Bird wouldn’t get anywhere near the Derby – the gelding wouldn’t have enough ‘Road to the Kentucky Derby’ qualifying points. Back then, though, participation rested on earnings in Graded races, and he had picked up almost $140,000 for winning the G3 Grey Stakes at Woodbine. Several horses dropped out of contention, as they always do, and Mine That Bird was in.
The fable unfolds like a tapestry, gold gleaming at every turn. Sunland Park is about 1,500 miles from Churchill Downs. Woolley could have put Mine That Bird on a plane, but instead he loaded him into a trailer behind his pickup truck and hit the blacktop for a 21-hour road trip.
“We’ve been doing that with horses for a million years. I don’t know why that caught on as such a big story,” he told the Amarillo Globe-News.
No big deal
It might have been because Woolley drove all the way with his right leg in plaster, having broken it in a motorbike spill two months earlier. With his left foot working the gas and the brake, both eyes on the road and one ear cocked for any sound from the trailer, the phlegmatic Woolley certainly had his hands full. “No big deal,” he said.
You’d have taken your hat off to him, if you were wearing one, which you almost certainly weren’t, because no-one does these days. Woolley was.
He wore it through the build-up to the big race, as anonymous a figure on the backstretch as a big Texan in a black stetson on crutches sporting a lavish horseshoe moustache could possibly be.
Mine That Bird was over 50-1 in a 19-runner field – the morning-line favourite I Want Revenge was scratched on raceday morning – and was similarly anonymous to bettors.
They liked new favourite Friesan Fire, winner of the Louisiana Derby, or Santa Anita Derby winner Pioneerof The Nile, or Florida Derby runner-up Dunkirk. Or they liked something else, but no-one liked Mine That Bird. And when he trailed the field by the length of a city block around the clubhouse turn, they figured they were right.
Mine That Bird moved closer, swished past a handful of stragglers on the turn, and as they made the top of the stretch Borel flicked him off the rail to pass a rival and then dived back to the inside. He was going fast now.
Scraping the paint
Mine That Bird was so far back that the racecaller and the cameraman missed him. He was so far back that he wasn’t covered in kickback from the sloppy track. But his jockey Calvin Borel – nicknamed ‘Bo-rail’ for his passion for scraping the paint off the fence – had been here before, and he knew the way out.
Borel had won the 2007 Derby on Street Sense from a similar position – he would also win the 2010 Derby on Super Saver, on whom he sat much closer – and he bided his time, watching it all happen like a Zen master, before unleashing his unconsidered mount on the ride of a lifetime.
Approaching the eighth-pole, Borel keyholed him through a gap on the Bo-rail so quickly that he was two, three lengths ahead before anyone knew what was happening. The longshot Mine That Bird was winning the Derby, and it became plain that racecaller Tom Durkin had no clue who this interloper was. He didn’t get out Mine That Bird’s name until the sixteenth-pole, when he was five lengths clear and widening.
“A spectacular, spectacular upset,” he vamped, clutching at straws. “Mine That Bird has won the Kentucky Derby. An impossible result here!”
Another part of town
Impossible, but true. Mine That Bird hit the wire 6¾ lengths clear, the opposition in another part of town, and Borel gestured wildly to the sky, to himself, to his horse. Then the little effervescent Cajun genius cried.
“I wish my mother and father were here to see what I have accomplished in my life,” he sobbed into the shoulder of post-race interviewer Donna Barton Brothers.
“Those cowboys came with a good horse,” said Bob Baffert, trainer of runner-up Pioneerof The Nile. And while Borel howled and high-fived his way back to the winner’s circle, a man in a big black hat waited quietly in his moment of glory.
“A lot of people didn’t know about you, didn’t know about your horse,” said NBC man Kenny Rice. 
Woolley had his answer ready. “They’ll know me now, won’t they?” he drawled, a touch acidly, before hobbling away to meet his miracle horse. He threw his arms around Borel, and his hat came off. Someone picked it up, and Woolley put it right back on.
The barely believable story of what was then the second-biggest upset in Kentucky Derby history was later immortalised in the film 50 to 1, although there would be no Hollywood ending for Mine That Bird, who ran second in the Preakness, third in the Belmont, and never won another race.
But, you know, Chip Woolley still wears that hat.
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