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High noon for the gunslingers with sights set on Triple Crown

Kentucky Derby winner Mine That Bird contests the Preakness today with a cast straight out of 'The Big Country', writes Chris McGrath

It was one against five. The one, Chip Woolley knew by sight – by stare, at least. They had glowered at each other, a pair of young toughs, down among the stables at La Mesa Park. But if Woolley's first instinct had been to dislike Mark Allen, his second was to reserve judgement in the interest of fair play. One against five became two against five, and they acquitted themselves pretty tidily. Or so they say. One way or another, they left the bar as blood brothers.

That was 25 years ago, in Raton, New Mexico – authentic cowboy country, under a spur of the Sangre de Cristo Mountains, on the Santa Fe Trail. Woolley, a former bareback rodeo rider, was galloping racehorses; Allen training them. They could not have known, then, that the brawl would ultimately lead, today, to another, far more momentous showdown. But they could scarcely have known that, even a fortnight ago.

For the odds against them, when they took a gelding named Mine That Bird to the Kentucky Derby – Woolley, as trainer; and Allen, along with Dr Leonard Blach, as owner – were far greater even than that night in the Annie Get Your Guns bar. Yet today they convene again in Baltimore as authors of the most breathtaking Derby performance in living memory – whether measured by the odds (at 50-1, exceeded only once in 134 runnings) or by its extravagant style.

If Mine That Bird can follow up in the Preakness Stakes, he will proceed to the Belmont Stakes with a shot at ending the longest drought in the history of the American Triple Crown, now stretching back 31 years to Affirmed.

On the face of it, moreover, this is another sporting romance to enrich American national mythology. Having changed hands, as a yearling, for just $9,500 (£6,250), Mine That Bird is a parable for the land of opportunity. As he approaches high noon, however, neutrals are increasingly hiding behind the shutters.

At first, only mean-spirited snobs could resent these men. Yes, sir. (That's the way Woolley talks. "No, sir." "Yes, ma'am.") Just look at them, in their badass gear. Depending on your point of view, in black, 10-gallon cowboy hats at Churchill Downs they either looked ludicrous, sinister, or just marvellously themselves. Woolley, 45, also wore a bootlace tie, a grim handlebar moustache, and impenetrable shades that gave him the look of some malevolent insect.

Then there were the crutches. Woolley recently shattered his right leg falling off his Big Dog Chopper. (A motorbike, since you ask.) That was why he had to drive his truck 1,466 miles from Sunland Park, on the Mexican border, using only his left foot. Attached to the truck was a trailer, and inside the trailer stood Mine That Bird.

When he reached Louisville, Woolley found that the adjacent barn housed the Godolphin horses – the elite stable of the royal family of Dubai, the biggest spenders in Turf history. This time, no doubt, the stares across the shedrow were bewildered rather than hostile. For what kind of circus could this be, to make neighbours of such incongruous men, in such a quixotic cause?

The Godolphin runners would finish eighth and 14th. Sheikh Mohammed must have looked at these deadpan men, up from the banks of the Rio Grande, and pondered his own, unrequited craving for this prize. Who are those guys?

Before the Derby, Woolley had saddled just one winner in 2009. And that was a Quarter Horse. Quarter Horses, hyper-bred for speed, are viewed as coarse freaks when compared to the equine aristocrats of the Bluegrass country. But many great American trainers started out with Quarter Horses, and so trace a lineage to the forgotten lore of the mustang men. The other Derby runners had all manner of tack, special chains and bridles and nosebands; the little gelding, in an old-fashioned, leather D-ring snaffle, might have galloped straight out of The Big Country.

Not that they got him cheap. Mine That Bird had made quite a splash in the racing backwaters of Canada when his previous owners cashed him in, last autumn, for $400,000 (£263,000). Allen and Blach sent the horse to Woolley, but he was beaten twice at Sunland before they took their chance in the Derby.

"Doc" Blach himself is one of the most respected Quarter Horse breeders of all time. Top trainers like Bob Baffert and Wayne Lukas have known these "cowboys" for decades. And they gasped as the veteran Cajun jockey, Calvin Borel, threaded his way along the rail on Mine That Bird. Passing the stands for the first time, he had been detached in last place; at the line, he was nearly seven lengths clear. Though his own horse came last, Lukas came bounding down from the stands, laughing and shaking his head. Baffert, having saddled Pioneer of The Nile to finish second, was in rather more acute shock.

But their adventure must be chronicled in ink, not treacle. Allen, for one thing, is the son of an oil services tycoon involved in a notorious political scandal in Alaska. And some would say that he has shown a rather Machiavellian side himself since the Derby.

Mine That Bird will still be an underdog today. Partly because so many people assume the Derby had to be a fluke; partly because he faces a new, daunting rival in the filly, Rachel Alexandra. She won the Kentucky Oaks – confined to her own sex – by 20 lengths, an unprecedented margin. Coincidentally, she too was ridden by Borel. Rachel Alexandra has since been sold to new owners, who decided to take on the males in the Preakness. And Borel rides the filly in preference to Mine That Bird.

Last weekend, the owner of Pioneerof The Nile gave a sensational television interview. Ahmed Zayat described a telephone call he had received from an unknown number. "Mr Zayat, you don't know me, I'm Mark Allen," said the voice. "Listen, I have a request for you."

Allen wanted his help in blocking the filly from the Preakness, by committing other entries in his ownership. Allen himself had another entry still eligible. Between them, with a safety limit of 14, they could ensure that Rachel Alexandra, as a late entry, would miss the cut. Still more remarkably, Zayat embraced the plot.

There was uproar among the fans, consternation among officials. The colt Allen was proposing as a block had not won once in nine starts. Rachel Alexandra could lap such a horse. This would be a public relations catastrophe for racing.

Citing pressure from the Maryland Jockey Club, Zayat eventually had a change of heart. He did not wish to be viewed as a bad sport. In turn, Allen also abandoned the idea, claiming that he had only ever wanted to keep Borel. "I ain't gonna do it," he told Sports Illustrated . "I was hanging out with my girlfriend and riding my Harley around and I got to thinking about it. It just ain't right. And when you do things that ain't right, it'll come back on you."

But the damage had been done. Woolley, to be fair, spoke decorously about Borel's desertion. "I can't blame him," he said. "I wish him the very best – because, you know, I would not be here without him." Rachel Alexandra, meanwhile, has been moved by her new, big-money owners from the care of an old-time horseman, Hal Wiggins, to the brash, prolific Steve Asmussen. Saturday will not be bad guys against good guys, outlaws in black against the sheriffs in pale. Life is seldom like that, and horses should not be used to make it so.

They tend to shoot from the hip down at Sunland Park, that's all. Mine That Bird's home racecourse is just down the street from the scene of a notorious shoot-out, in 1881. The "Four Dead in Five Seconds Gunfight" was one of the most notorious of the Old West. So two against five – that was really not such a big deal. How about one against 30,000? How about all the foals, born three years ago, among which only one could win the Derby? Asmussen has saddled more thoroughbred winners in 2009 (over 200) than Woolley in the past 25 years (178). But one gelding, one filly – that's a fair fight.

"I came [to Churchill] asking for autographs, and left signing them," Woolley said. "Nothing in your life could prepare you for something like that. I'm talking about people running up to you, and wanting to take pictures, and your phone ringing 6,000 times a day. It has made life much more hectic, but at the same time it is enjoyable. I mean, you know, you just wake up every morning, thinking: 'Man, I won the Derby.' And that is a major thing, you know."

Yes, sir.