The long, winding (but not dirt) road to the Derby
Texans owner McNair attempts to win Kentucky Derby, Oaks with a pair of mystery horses
By Mike Wilkening
May 1, 2008
For Texans owner Bob McNair’s thoughts on his team’s draft, check out Friday’s edition of “The Way We Hear It.”

This isn’t Bob McNair’s first trip to the Kentucky Derby, and it’s unlikely to be his last. And the story of how the Texans’ owner got here — and how his horse, Cowboy Cal, became one of the most unlikely entrants in the field — is a tale of how horse racing is changing while staying the same.
Squint at Cowboy Cal's racing record and you might see shades of Barbaro. Cowboy Cal, like the late 2006 Derby winner, captured the Laurel Futurity and Tropical Park Derby in impressive fashion on the turf. That’s what Barbaro was four months before his Kentucky Derby tour de force: A really nice grass horse. Even when he won twice on the dirt before the Derby, doubts lingered.
Which brings us to the curious case of McNair’s horse, who has run only once on dirt — his racing debut — and was soundly beaten. “He’s like a lot of horses in that in his first start he didn’t do all that much,” McNair said.
So why is a top-flight grass horse in the Kentucky Derby? Because Cowboy Cal (pictured below) finished second in the Blue Grass Stakes at Keeneland Race Course on April 12, almost wiring a field that included Pyro, one of the Derby favorites.
The Blue Grass has long been one of the premier Derby prep races, but it has been run the past two years on Polytrack, the artificial surface that’s billed as a safer alternative to dirt. This has led to surprising results in both runnings. Last year, favorite Street Sense — who went on to capture the Derby three weeks later — finished second in a race that was much like a turf race: very slow early, very fast late.
Turf horses, the theory goes, are more prone to like Polytrack than horses bred simply with an affinity for the dirt. And so it went with Cowboy Cal, who got an easy lead and led for much of the race before holding for second.
Now McNair is banking on Cowboy Cal, trained by Todd Pletcher and given a 20-1 chance of winning the Derby, liking the dirt more the second time around. His breeding suggests he may take to the dirt at some point; his sire, Giant’s Causeway, was second in the 2000 Breeders’ Cup Classic, a race run at the same track (Churchill Downs) and distance (1¼ miles) Cowboy Cal will be trying on Saturday.
McNair expects Cowboy Cal, breaking from post position No. 16, to be a few lengths off the lead early on. Race favorite Big Brown, breaking from the post position closest to the grandstands (No. 20), could very well be on the lead as the field makes the calvary charge into the first turn. McNair believes Cowboy Cal can be taken off the pace more easily than Congaree, his 2001 Derby entrant who ran too close to a wicked early-speed duel and did not finish with any authority. What’s more, he believes Cowboy Cal has a second gear, one that his last Derby horse, Bob and John, did not have.
“What we would hope is that the speed horses get out and we’re in that second flight,” McNair said.
Of course, there are some who will believe Cowboy Cal won’t be a factor in the least, given his poor first try on the dirt. And he isn’t the only entrant facing such scrutiny. Colonel John, likely to enter the starting gate as the second betting choice, has never run on dirt, racing exclusively on artificial racing surfaces in California. Colonel John has worked well over the Churchill surface, alleviating the concerns of some handicappers, but it remains to be seen how he’ll race over it on Saturday.
Ironically, the second choice in the Kentucky Oaks, the prestigious race for three-year-old fillies run the day before the Derby, is likely to be McNair’s Country Star — and she has never tried the dirt, either. Her credentials are considerable: a pair of wins in top filly races on artificial surfaces as a two-year old. Like Cowboy Cal, she could very well love the dirt; her sire, Empire Maker, was the favorite in Funny Cide’s Kentucky Derby five years ago. But she comes off a surprising loss at Keeneland on April 5.
McNair had two theories as to why she ran poorly in her season debut. She had a wolf tooth, “which is sort of like a wisdom tooth that doesn’t break through,” McNair said. Also, McNair noted that trainer Bobby Frankel suggested a workout in the days leading up to the race in company with Ginger Punch, the three-year-old champion filly in 2007, may have taken something out of Country Star. But all is well now, McNair said Wednesday.
If that wasn’t excitement for McNair this weekend, there’s this: He owns one of the favorites in the 2000 Guineas, the famed English turf race for three-year-olds. Raven’s Pass may go off as the second choice in the betting. McNair is hoping for a turf course on the firm side for his colt, a son of Elusive Quality, a horse best known for siring Smarty Jones.
As much as the surface debate hangs over horse racing today — and as much as the public loves a feel-good, long shot, seemingly ordinary horse winning on the biggest stages, a la Funny Cide — this much remains the same: deep-pocketed owners with regally bred thoroughbreds are not going to be wanting for spots in the gate on the big-money days. Cowboy Cal and Country Star, their pedigrees suggest, can run on anything. That doesn’t come cheap.
But take nothing away from McNair. He has invested millions in a thoroughly impressive operation. In 14 years, McNair’s Stonerside Stable has raced 59 stakes winners. It has bred 34 individually as well as 18 in partnership, most notably 2000 Kentucky Derby winner Fusaichi Pegasus.
In short, Stonerside is what the Texans are aspiring to become: consistently competitive at the highest levels. McNair was asked Wednesday if his other major sporting venture — the Texans — was coming along as quickly as he would have liked as head coach Gary Kubiak enters his second season on the job and general manager Rick Smith enters his second season.
“I think the way we look at it is, ‘Are we making adequate progress?’ ” said McNair, who praised Kubiak and Smith for their work to date. “I don’t think you can set a timetable because there are circumstances beyond your control.”
He wasn’t speaking about horse racing, but he easily could have been. Two years ago, Bob and John got bumped hard twice coming out of the gate, once by Barbaro, who bulled his way into ideal position entering the first turn. The one-paced Bob and John was shuffled back. You don’t need to read the footnotes to know what happened with Barbaro, but they are illustrative in the case of poor Bob and John, who was “finished after seven furlongs.”
With three furlongs left in this Derby, McNair would love nothing more than to see the speed horses dropping back.
“Then we’ll get to the top of the stretch,” McNair said of Cowboy Cal, “and see if the second gear is available or not."
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