How I’d Bet The Kentucky Derby

The Kentucky Derby runs in the early evening on Saturday (6:24 PM ET, NBC). Here’s the rundown on the 20-horse field along with the misguided notions for how this writer would be it.

California Chrome (5-2):
Let’s start by noting that the favorite usually doesn’t win the Derby, and in fact, often lags well behind. Last year was an exception when Orb came through as advertised, but it was the proverbial exception that proves the rule. California Chrome lacks an experienced jockey and trainer, and even though he won the prestigious Santa Anita Derby, he’s hardly the only horse in Churchill Downs this weekend with a nice resume. As you can see, I’m skeptical that this favorite is going to hold serve.

Wicked Strong (8-1)
Danza (10-1)

These are my two favorite names in the Derby, and their odds on the morning line draw them together as the top challengers. Wicked Strong is named in honor of the victims of the Boston Marathon bombing (Boston Strong was already taken). Danza is named after the actor Tony Danza, and I’ll cop to having been a big fan of Who’s The Boss in the late 1980s and early 1990s.

Wicked Strong won the Wood Memorial, a big race in New York in the Derby Prep season, while Danza won the high-profile Arkansas Derby. Danza has been prepped by top trainer Todd Pletcher.

Intense Holiday (12-1)
Tapiture (15-1)
Wildcat Red (15-1)
Ride on Curlin (15-1)
Samraat (15-1)
General a Rod (15-1)

If you wanted to take these six horses and just bet the same amount on each, knowing you’d turn a profit so long as one of them won, I couldn’t fault the strategy. They’re all in what I’d term reasonable range—the odds are just big enough to be enticing, but not so big that you’re throwing your money away.

Tapiture looked on track to be the early Derby favorite after a win in the Southwest Stakes, but the horse failed to improve, finishing second in the Rebel Stakes and fourth in the Arkansas Derby. Those races are in escalating level of prestige, so Tapiture clearly suffered as the competition improved. But his trainer, Steve Asmussen, is one of the best.

Asmussen is also under fire from PETA (People For The Ethical Treatment Of Animals). While I generally think PETA’s priorities are screwed up (protecting animals, but not unborn children), when it comes to the tactics of the horse racing industry, they’ve usually got a valid gripe. I won’t judge the specifics on the Asmussen case, but just sayin’.

Jockey Calvin Borel has won the Derby three times, including back-to-back in 2009-10, and he’s aboard Ride On Curlin. Another good jockey is John Velazquez, who rides the Pletcher-trained Intense Holiday.

Dance With Fate (20-1)
Chitu (20-1)
Medal Count (20-1)
Candy Boy (20-1)

Dance With Fate won the Blue Grass Stakes, a marquee prep race run at Keeneland, one of the sister tracks to Churchill Downs on the Kentucky circuit. Chitu on the Sunland Derby, a lower-profile prep race in Arizona. On the surface, it doesn’t look dramatic, but a win in the Sunland was all that Mine That Bird had to recommend him in 2009 before he won as a 50-1 longshot.

Vicar’s In Trouble (30-1)
Uncle Sigh (30-1)
Vinceremos (30-1)

I’m a fan of Rosie Napravnik, the jockey for Vicar’s In Trouble. She’s sort of the horse racing version of Danica Patrick, making her way in a world that’s filled with a lot of pseudo-tough guys.  And unlike Danica, Rosie actually wins races. One of those was the Louisiana Derby with Vicar’s In Trouble. She also won the lower-grade Lemcote Stakes aboard this mount.

Harry’s Holiday (50-1)
We Miss Artie (50-1)
Pablo Del Monte (50-1)
Commanding Curve (50-1)

At this writing, Pablo Del Monte is not official, but appears to be set to take the place of Hoppertunity, one of the favored horses who has to be withdrawn for health reasons. Kudos to trainer Bob Baffert for not pushing the horse, and hopefully Hoppertunity will be ready for the Preakness Stakes in two weeks.

I find We Miss Artie to be the most intriguing of this group, if only because he has won a stakes race (albeit a low-grade race at Cincinnati, a minor track). And he does have an able jockey in Javier Castellano, one of New York’s best, and Pletcher is the trainer. The combo of trainer, jockey and longshot odds makes this horse interesting.


The four horses I would go to the mat on would be…

Intense Holiday
Wicked Strong
Vicar’s In Trouble
Dance With Fate

My win bet is going to be with Intense Holiday for $6. Then I’m taking all these horses and putting them into an exacta and trifecta box. In this case, a $2 bet, means you bet $2 on every possible combination order of finish. The amount of the wager is $60, but so long as the top two finishes are in the box, I can cash the exacta (which has averaged $769 over the last two years) and if the top three are in the box, I get the tri (which averages in the thousands).

At this point, I’ve bet $68, so to keep it an even number and to reflect my interest in a longshot, I’ll slap two more dollars on We Miss Artie to win. That’s $70 down the tubes—at least hypothetically. 


May 5 Postscript: Well, apparently all that’s needed for a favorite to win is for me to point out the historical record of how favorites do at the Kentucky Derby. It reminds me of 2011 in the baseball playoffs when I went on a national podcast and said that the historical record in the Division Series showed there were a lot of sweeps. Over the next two years, seven of the eight series went the full five games.

Anyway, terrific performance by California Chrome. The way he pulled away from the field at the end makes me believe he can win the Belmont Stakes in June, a race that often breaks the hearts of Triple Crown aspirants because of its length. The Preakness is the shortest of the three races, so we’ll see how he handles that in two weeks.

Commanding Curve finished second and undoubtedly destroyed a lot of exotic boxes around the country. With Danza and Wicked Strong placing third and fourth, I’m sure a lot of bettors were in line to hit the trifecta or super, especially if they boxed the horses, but a longshot coming in second place renders it all for naught.