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."


Leave a Comment:

steve from st louis

Jason, nice job. Stars like Keith are exactly what racing needs: good publicity. Racing and Hollywood always worked well together. When Jack Klugman and Telly Savalas were Derby-bound owners, racing was instantly chic. Owners like Bobby Flay and Jim Rome introduce racing to a whole new generation of fans. Pulling casual fans away from mindless slot machines is racing's biggest challenge.

10 Feb 2012 3:32 PM

We don't have to worry about this Toby Keith colt. Fed Biz is going to win the "2012 Kentucky Derby".

Just sayin...

10 Feb 2012 6:24 PM

How refreshing to see a celebrity who is intelligent & actually knows what he's talking about- unlike Mike Repole.

10 Feb 2012 6:31 PM

I love this story!!!!!!!  Thank you Jason, excellent work!  I have been saying for years that country music and horseracing "fit like a glove" too and this is it coming to fruition.  Toby is a mega talented man, love the name Reckless Jerry, and love how dedicated Toby is to the sport and his music career.  It's all good, all positive, this is great for the sport.  Toby can singlehandedly increase the fanbase.  I get a big kick out of how Toby thrives on studying the pedigrees like us.  A very talented man whose heart seems to be in the right place on all levels.  I'll be hoping that Reckless Jerry is one in the Derby post parade, how cool would that be?

10 Feb 2012 6:43 PM
Criminal Type

I am thrilled for Toby Keith, I hope Reckless Jerry gets to the Derby...Let's see if Toby can get the words to My Old Kentucky Home correct. He is one of few country singers I will even listen too.

Steve, Everyone knows slots are for LOSERS.....the serious racing fans play BlackJack....LOL.  

10 Feb 2012 7:16 PM

I love it == Toby Keith, smart, down to earth, really investing in the game, I am rooting for him to get there!!

10 Feb 2012 8:59 PM
Paula Higgins

Another interesting blog Jason. He sounds like he knows his horses. I hope he has much success. My husband is a fan of his music.

10 Feb 2012 9:14 PM

I'm really glad Toby Keith is so vested in horse racing. Maybe if he is successful, other country music celebrities will also begin investing in the business.

10 Feb 2012 11:46 PM

Toby Keith is showing to be a good owner by letting his horse progress. The Southwest will be a good test for Reckless. This will show if he is ready to move on to the Rebel or stay in sprints.

11 Feb 2012 12:11 AM

The Southwest is coming up tough and the prospect of Reckless Jerry marking the board is very remote. The first four finishers in the Smarty Jones will be returning in the Southwest and Speedy Bob’s Secret Circle. My money will be placed on the Shadwell colt NAJJAAR. The distance of the Southwest is bit too short but he will be wearing blinkers for the first time that might help him to stay a lot closer to the pace. If they go too fast the race will be his to the taking.  

11 Feb 2012 12:42 AM
Matthew W

Santa Anita Sat....Race 8, speed clogged, looks like #13 Hout Bay will be in the exacta, but I also like, no love--#2 Miss Sea Cup, am hoping Flores can ease her back/ease her out--if he does she will be very tough, that is an underated filly....Race 9, The San Marcos is a Gr 2 but it has the look of a Gr 1--Bourbon Bay drops big weight, and he loves the course--he appears to be the exacta horse, and favorite Sanagas looks real nice--my longshot is another David Flores horse, #7 Slim Shadey--last race was visually impressive, and that can be very deceiving as it was vs much softer--still, I know what I saw, Slim Shadey will be a huge price, I'll box him with Bourbon and Sanagas and play Slim to win/show....Race 8 will box Miss Sea Cup/Hout Bay, and play Sea Cup win/show, go David Flores, he's my longshot jock tom at Great Race Place!

11 Feb 2012 2:14 AM

Fed biz the derby winner?....really u have to race horses to get to the derby...having a public workout does not win derbies...just saying'

11 Feb 2012 9:01 AM
Blind Luck

Well, I always enjoy Toby as an Artist of country music and now to learn he is so into the horses, well I am totally in love now!  Go Keith, and bring all your fans with you.

11 Feb 2012 9:29 AM
Age of Reason


This is somewhat off topic, but John Shirreffs was recently announced to head an advisory board to the CHRB on medications and usage thereof. Any word on how Shirreffs tends to come down on the issue? What all drugs did he use with Zenyatta, Giacomo, Life Is Sweet, Mr. Commons, etc.? Does he have any recent infractions? ('Inquiring minds want to know!' lol)

11 Feb 2012 11:13 AM

Great job Jason.  Best of luck to you Toby.  Jason, did you see Black Caviar ?  Wow she is by far the best mare to ever race.

11 Feb 2012 12:09 PM

Matthew W-

I had Hout Bay to finish off a $2200 P4 in her maiden when she motored home impressively and looked like a player in the 3YOF division. However, something went awry as she has produced five dull efforts since. Plus, she's a dead closer on a speed highway of a surface. Miss Sea Cup is a value will likely climb to 10/1.

Slim Shadey is interesting. His win was better than looked but this is a VERY salty San Marcos, in fact the only I can remember being tougher would be the year Tin Man and Johar squared off. This isn't Sanagas' target race and, more importantly, I think it's too short for him. He got a dream position and pace last out on a course more to his liking. He beat up Norvsky & Bourbon Bay last out but this is a completely different scenario this time. Not to mention The Usual QT ran like a short horse last out and there are some strong angles for a price here.

Very nice card today. The supposed super horse Welter Weight will be favored vs Stirred Up, who finished like a freight train against the bias in his 1st out 12 days ago. Throw in the other Baffert who will be running with the course profile,  the Hess who made an large backstretch move in first out on the turf, and the Talamo stretch out who just worked 44.8 which was 9 ticks faster than the next fastest for the distance and you've got an abnormal maiden heat.  

11 Feb 2012 12:46 PM
Bob from Boston

This is just what racing needs.  A war hero who sings brilliant songs like, "Red Solo Cup."  Stick a boot in their a$$, it's the American way, Toby.  I hope Kim Kardashian and Snookie get involved in the sport too.  Who needs the "celebrities" from the racetrack of yesteryear?  Bing Crosby?  Frank Sinatra?  Who here would take White Christmas and The Way you Look Tonight over Red Solo Cup?  George Strait needs to belly up to the rail as a high profile owner too.

11 Feb 2012 1:02 PM

Good luck to Toby and Reckless Jerry. I hope they make it to the Derby and run well but I wouldn't toast that Red Solo Cup just yet.

11 Feb 2012 4:12 PM

I'm wishing Toby and his horse Reckless Jerry the best!  Being an 'okie' myself, I love it when an Oklahoma horse and owner have a chance to make it to center stage on a national scene.  Good luck Reckless Jerry in the SW Stakes ;-)

11 Feb 2012 5:19 PM

I'd rather go the dentist for a cleaning than a Toby Keith concert but I hope he has success with Reckless Jerry.  How about Hymn Book on the off track!  Decent time too.  

11 Feb 2012 5:40 PM
Matthew W

Mathieu--I was visually impressed with Slim Shadey in his last race--I also took note of his recent vet scratch, then they took another week to work him--I played him yesterday, win/show, when Usual QT scratched I pretty much "knew" we would have the lead--Slim is another horse who was very well meant as a two year old, then he went sour as a three year old--all the more reaso0n to get on board  when he finally did get it together, as I said, his most recent race was rock solid, and I was pleased with how Flores took what they gave him--namely an easy lead--he needed it yesterday, but it should be noted, Slim Shadey might have been a bit of a short horse, with the recent vet scratch and all...he'll fetch a good price next time, and he won't need the lead!

12 Feb 2012 12:19 PM

Very cool read.  I also, love my red solo cup!

12 Feb 2012 1:19 PM

I thought Union Rags was the be all ....end all...

How could Castellano pick Algorithms over Union Rags?

I bet we all know the answer to that.

Let's see here...

We have a colt out of Bernardini and a colt out of Dixie Union.

Mmmmmm.... Wonder who the mile and a quarter pedigree is....LOL!

...Now we know why Zenyatta's connections chose Bernardini over Dixie Union.


We all know Dixie Union colts stop after a mile and eighth.

Just sayin...

12 Feb 2012 11:31 PM

Matthew W:

Good call on Slim Shadey in the San Marcos.  What did you think of Bodemeister's "scintillating performance" in the 3rd on Saturday?  By Empire maker out of a Storm Cat mare, this guy looks to have a bright future.  I hope Baffert doesn't rush him but he sure looks good.

13 Feb 2012 7:48 AM
Union Buster

Castellano opts OFF Union on the Rags for the FOY. That tells a big story, Union on the Rags will not win the KY Derby!! Pity the fools who wasted Futures money on him at a measley 7/1.

13 Feb 2012 9:11 AM
Aaron McC

To those of you who think that Castellano's choice marginally depreciates Union Rags: I suspect the horse's distance ability as well, and Algorithms might well be the better choice.  But Castellano did "agonize" over the decision, right?  Or was the "agony" just jockey politics ...? In any case, Union Rags does look pretty solid, and Leparoux, I'm guessing, is not in agony over his pick up mount.  

13 Feb 2012 1:14 PM

Castellano gave up the Derby winner but he went with the trainer who will have the most talent year to year.  Union Rags has grown into a monster and will be your Derby winner if he can make in the gate healthy.

13 Feb 2012 2:27 PM
Bob from Boston

Well, that settles it.  Union Rags has zero chance of winning the Derby.

13 Feb 2012 3:35 PM

You don't take off of Union Rags if you think he is the 2012 Derby winner.

Two year olds and three year olds are a whole different ballgame. Very few high profile two year olds turn into monster three year olds.

Castellano is choosing Algorithms for a reason. He could be wrong, but most likely there have been "signs" given to Castellano that tell the tale.

Castellano knows horseflesh and once he was on Ghostzapper, he never wanted to leave him.

13 Feb 2012 5:03 PM
Paula Higgins

Age of Reason, I think John Shirreffs is pro-Lasix. I am sure I read some comments he made about it.

Draynay, Black Caviar is phenomenal, no doubt about it, but lets see if she can get the longer distances before we pronounce her the best mare ever. Also, lets see how she does in Dubai and in England. Would like to see her on dirt too. But I do get your point. She is something special.

13 Feb 2012 8:51 PM

Castellano jumping ship is no big deal.  Jockeys and their agents are not the most astute handicappers, a fact that has been proven so often over the years.  It reminds me of Willie Shoemaker, who won three races in three rides leading up to the Derby on Northern Dancer, an exhibition, the Flamingo and the Florida Derby, then jumping off and committing to Hill Rise, one of the biggest blunders of his career.  Even at that, little did trainer Horatio Luro know that he had a future HOF rider committed to ride the Dancer already.  When he was a two year old Ron Turcotte rode him four times and yet wasn’t considered good enough to ride him when he went south of the border to commence his TC campaign, the same Ron Turcotte who would ride back-to-back Derby winners on Riva Ridge and Secretariat, win 5 of the 6 TC races during that two year span and also break the 25 year TC drought.

14 Feb 2012 1:01 AM

Union Rags got lucky.  Julien knows Churchill as well as anyone.  A top young jockey with a top young horse.  Watch out.  Fountain winner for sure.

14 Feb 2012 1:18 AM

Secretariat - I think Draynay is spot on in the Castellano analysis.  Castellano went with Algorithms because of Pletcher and the fact that Castellano is getting first call on many of Pletcher's horses.  He is a relatively young jockey and it was the smartest business decision.  Don't think it speaks at all to Union Rags' future.  Also, I think Castellano is great but Union Rags may have just traded up a bit when getting Julian L., in my opinion at least.

14 Feb 2012 9:21 AM

Regarding Javier Castellano's decision to go with Algorithms; I agree with all who see this as a business decision.  This is the kind of situation jockeys hope to get to in their careers. Best of luck to Javier and Julian.  

2:24 and Draynay, I agree that Union Rags may be better off with Julian, especially after some were calling for Javier's head after the BC Juvenile saying he couldn't control his mount, letting him drift out.

Looking forward to the FOY, shaping up to be a competitive race with some classy colts and others with a lot of upside.  I doubt that Michael Matz will have Union Rags fully cranked this early, just looking to keep him moving forward.  If the speedway is dry, I look for Discreet Dancer to cook 'em all.

What to do with this fever!    

14 Feb 2012 11:35 AM
Jason Shandler

I just wrote a new blog on the Castellano decision...

14 Feb 2012 12:52 PM

Jason, you have to get Toby to blog with us like Mike Repole did!!!  Tell him to write a song about Reckless Jerry!  I hope we see other country music stars become owners as well.  What a boost to the industry that would be. C'mon Jerry!!!!!!!

16 Feb 2012 7:42 PM

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