Toby Keith on 'Reckless' Path to Derby

At a time when horse racing is struggling to stay in the spotlight, having big-name owners with star horses can be a major shot in the arm for the industry. We've seen that over the past few years with people like Bobby Flay and Mike Repole.

There may be no bigger celebrity with a passion for horses than country music superstar Toby Keith. As you may remember from last year, I wrote a story on Keith when his talented 3-year-old Sherriff Cogburn made an appearance on the scene. Unfortunately, Sherriff Cogburn, who placed in both the Iowa Derby (gr. III) and West Virginia Derby (gr. II), has battled injuries during his short career and a tendon injury forced him to the sidelines.

But Keith is back again, this time with a colt who has not only showed talent but, knock on wood, has stayed healthy in the early stages of his career. His name is Reckless Jerry, and he is by Keith's prized stallion Cactus Ridge. Reckless Jerry is on his way to the $250,000 Southwest Stakes (gr. III) Feb. 20 at Oaklawn, where he is likely to be one of the favorites.

Reckless Jerry, a homebred out of the Crafty Prospector mare Miss Moneywise, won twice as a juvenile including a 4 1/4-length allowance romp at his home base of Remington Park, and also finished a close second in the Springboard Mile. He began his 3-year-old season with an unlucky nose defeat in the Smarty Jones Stakes, where he broke from post 12 in the one-mile, two-turn contest and was wide the whole way. He wound up just missing to Junebugred, but apparently earned a higher Ragozin number in doing so. Keith has entertained lucrative offers for the chestnut colt.

Keith said Reckless Jerry has shown just as much promise, if not more, than Sherriff Cogburn had at this point in his career. Kenny Smith trains him.

"We're more hopeful with this horse," said Keith, a multi-platinum recording artist who was named Billboard's Country Artist of the Decade. "He's blooming now. Cogburn was kind of a precocious 2-year-old."

As I pointed out in last year's story, Keith is not your average celebrity owner who is just throwing his money around to attract attention. Horses are a passion for him, as he is involved in every aspect of the industry. He owns a 330-acre farm in Oklahoma where he keeps about 110 mares and is very active at sales, where he not only buys to race but is an active pinhooker. In the past, Keith bred most of his mares to Cactus Ridge, the brilliantly fast 2-year-old that he raced in 2003. But just recently he bought a half-interest in 2010 Florida Derby (gr. I) winner and Kentucky Derby runner-up Ice Box, who will stand at Calumet Farm.

Keith plans to move many of his mares to the prestigious Calumet, where he will breed them to his two stallions. One of his favorite aspects of the sport is pedigree patterns and nicking, and he studies it relentlessly. He uses TrueNicks to help him with his breeding selection process.

"I wanted a place that didn't have too many horses," Keith said. "I'm going to breed a lot of mares to these two horses. Sons of Pulpit fit Cactus Ridge mares like a glove. So I wanted in (on Ice Box). I was breeding to sons of Pulpit anyway, so it made sense. Ice Box is a good-looking bugger too. Now I can keep most of my mares in the same vicinity."

Keith knows his pedigrees, and isn't under any false illusions that Reckless Jerry has the ideal pedigree for classic races. Cactus Ridge, who was undefeated in four starts, won his longest race at a mile. Miss Moneywise was a sprinter, as was her sire, Crafty Prospector. But he says if you dig a little deeper there is some distance in the pedigree.

"A lot of people look at the pedigree, Cactus Ridge out of a Crafty Prospector, and they say he ain't gonna go very far," Keith said. "But his second dam is by Shadeed, his third dam is by Graustark, and his fourth dam by Princequillo. Cactus Ridge's dam is by Danzig and the dams under that were group I winners in Europe. So we're going to find out.

"We'll run him another mile here, then stretch him out more, and then stretch him out a little more. We'll see what we got. We know he gives that effort every time he goes out. It's not the perfect pedigree to bet your hat on, but at same time when you look at the horses underneath in the pedigree you never know what you're going to get. He's shown a lot of will and heart at the end of races."

Keith, who races his horses under the name Dream Walkin' Farms, has had several stakes winners during his time in the sport and has been a successful pinhooker. But like everyone else, he dreams of having a horse take him to the Kentucky Derby. If Reckless Jerry should happen to take him there, it would be a win-win for everyone.

"I've been in this for 15 years and had some nice stakes winners, but have never been able to hold one together past February," he said. "Cactus Ridge was undefeated and headed to Breeders' Cup when he broke down.

"The Derby is so prestigious. It means so much to your farm to get to go. It's a big deal–the atmosphere, the celebration, the festivities around the event. I know it would be a great experience for me and I would hope it would be great shot in arm for horse racing too. I have a lot of celebrities around me all the time, so it might be a good thing for the sport."

"Reckless Jerry doesn't have any holes in him. Now we'll see if he keeps improving. If he does, he will be tough. If not, he is what he is.

"It's always special when you have homebred. I kind of compare it to songwriting. I have written most of my songs and have had a lot of success at it, but I also had four of five hit songs that I didn't write. They're nice too, but when you sit and write it yourself, it's just a little more special. It's the same with a homebred."

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