BOMBS AWAY: Five Live Long shots to Die For, A 2009 Kentucky Derby Preview

Pete Hausler


“Twenty fucking five to one
Me gambling days are done
I bet on a horse called the Bottle of Smoke
And my horse won.”

—From “Bottle of Smoke” The Pogues

Just after 6 p.m. on Saturday May 2, twenty horses will load in two starting gates under the twin spires of Churchill Downs, while millions around the world watch on television, while one-hundred-thousand-odd bourbon-sotted bettors watch live, holding their mint-julep breath until that starting bell rings. The gates burst open to a roar and a trill, and even people who have never placed a bet in their life, who don’t know a quarter-horse from a quarter-crack, are at least vaguely aware that the race is going off.

So, why should you care? Well, because you can make a lot of money on Derby day. The Derby is always loaded with live long shots, or ‘overlays’ in the vernacular. An overlay is a very good horse who has been overlooked at the betting window for various or no good reason, and therefore his odds are higher than they should be. In assessing a race, an overlay is a horse who seems to have a better chance of winning than his odds indicate.

Why are there so many long shots in this year’s Derby? The same reason there are every year: Because everyone wants to run their three-year-old in the Derby. There are a maximum of 20 spots, and any given year, 15 or so of those horses have a legitimate shot to win it. And because, mathematically, they can’t all be favorites, a lot of those horses will be overlooked, and their odds will rise. Which doesn’t mean they are bad horses. It just means that the favorites have gotten more attention. There is only one way to cash a big ticket big: show a little fortitude at the betting window by showing tough love to the vaunted favorite(s).

Favorites always look good on paper—that’s why they’re favorites. The last two years have been kind to the favorites, with Big Brown romping in last year’s Derby, and Street Sense the year before that. But this year I’m betting that we’re going to cycle back around to a long shot winning. Overall, in the last 25 years, only Big Brown, Street Sense, Smarty Jones (2004) and Fusaichi Pegasus (2000) have won as the chalk. The blanket of Roses in this time period has usually gone to a long shot. Why?

A variety of factors, but mostly because three year old horses are still learning the game, are still maturing physically and mentally, and therefore tend to run inconsistently from race to race. One thing to always remember when betting horses: they are athletes––splendid athletes––and like human athletes, subject to under- or overachieving, to monster runs or dismal failures. Maybe a horse wakes up one day and doesn’t feel well, or has a nagging injury, maybe he loves or hates a particular track. To paraphrase Mickey Rourke (paraphrasing “The Mickey Mouse Show”) in the film “Angel Heart:” Derby Day is anything-can-happen day.

The mother of all recent Derby long-shots would be 2005, when the previously underwhelming gray colt Giacomo crossed the wire at 50-1 (followed closely by the 71-1 Closing Argument). If you somehow were savvy or lucky enough to take a chance on Giacomo, a $2 win bet paid $102.60. The exotics were even kinder: exacta, trifecta and superfecta wagers (wagers where you guess, in the correct order, the first two, three, or four finishers of a race, respectively) paid $9,814 for the exacta, $133,134 for the trifecta and a jaw-dropping $1.7 million for the superfecta (these were all based on a $2 bet).

Now, granted, these 2005 numbers are a (not-so-)gross aberration from normal or even average exotics payouts, and aren’t likely to be duplicated any time soon. But, one thing every bettor is good at is dreaming, whether it’s the professional dropping $500 a day on the races, or the once-per-year, casual fan betting on a cute name in the Kentucky Derby.

So, then, let’s take a closer look at this year’s field. I won’t mention every horse; instead, I’ve picked out five primary long shots who might be worth taking a flyer at, and added a few honorable mentions for luck. For the odds in this article, I’m using the official morning line track odds, set by Churchill Downs’ oddsmaker, Mike Battaglia. I mention this, because by the time you read this, by the time the race goes off, these odds will have changed. The number in parentheses next to the horses’ name is his post position/program number; remember, you always bet by saying the horse’s program number not his name.

West Side Bernie (post 1) at 30-1: Two wins out of seven lifetime races, but six of those races have been graded stakes, the most competitive class of race. In other words, this guy has been ambitiously placed in the Gifted and Talented class, and even if he’s not getting straight-A’s in the smart-kid tract, he’s being well-tested every race. Another plus: his jockey, Stewart Elliott, won the Derby in 2004 on Smarty Jones, so he has experienced the zoo of Derby week.

Musket Man (post 2) at 20-1:  A horse who has won 5 of his 6 races and is at 20-1 odds? Why is that? Well, the knock on The Man is that his sire, Yonaguska, was known more as a sprinter. So the conventional wisdom says that the sire’s progeny can only sprint, and specifically, that MM won’t make the long, mile and a quarter Derby distance. Dunno, this always seemed a half-baked argument to me, because sometimes the apple DOES fall far from the tree, and at 20-1, I’m willing to risk that this 5-for-6 horse can run beyond his sprinter’s pedigree.

Regal Ransom (post 10) at 30-1: One of two horses in this race owned by the international powerhouse Godolphin Racing, out of Dubai. The other Godolphin horse, Desert Party, is also a long shot (15-1), but I’m touting Ransom because of a piece of super-insider track wisdom I’ve come by: if a big name outfit has two or more horses in a big race, look to the one(s) with higher odds to win. Why? Not exactly sure, it just seems to happen enough to––what’s that Latin expression––nota bene. Regal Ransom has speed, so look for him to be on the front end early. Plus, his daddy sired the 2003 Derby winner Funny Cide (and yes, in this case, I’m willing to hypocritically hope that the apple doesn’t fall far).

Chocolate Candy (post 11) at 20-1: A California horse who has run multiple times against (and finished behind) this race’s morning line favorite, I Want Revenge, and second favorite Pioneer of the Nile. I like this ‘turning the tables’ angle, where he’s right up there with these other two, deserves to be in the same race, and I feel it wouldn’t take much for him to actually pass them on Saturday. He’ll take a lot of “name” money, because his alliterative name kinda rolls off the tongue, so his odds will be lower than 20-1 at race time, but still fair value

General Quarters: (post 12) 20-1: A feel-good story, whose 75-year-old trainer, Tom McCarthy, is in the Derby for the first time. GQ is the only horse in the race with a win at this track (in fact, only two others have even raced previously at Churchill), so you know he likes a track often considered quirky. Plus, Kentucky-based jock Julien Leparoux will be riding at his home base, a fact that shouldn’t be overvalued, but nonetheless, is worth something.

And two bonus Honorable Mention horses for luck: There are two 50-1 horses in here who bear mentioning for one reason: their savvy trainers, time and again, have shocked and amazed bettors and fellow-horsemen, by entering their seemingly-crap horses in big races and winning at deservingly-huge odds. In fact, there’s an old saying around the track that describes this very scenario: Big Race, Big Trainer, Big Price, Big Bet. The trainers are Nick Zito, training Nowhere to Hide, and D. Wayne Lukas, training Flying Private, and this adage fits them to the proverbial T. You ignore these two trainers and their apparently-overmatched horses at your own peril. Just saying.

There’s absolutely nothing wrong with the favorite, I Want Revenge, it’s just if you bet him to win, you won’t win a whole lot of money. In “The color of Money,” Paul Newman’s Eddie Felson observed  “Money won is twice as sweet as money earned.” So let’s go ahead and dream a little long shot dream, take a flyer on a 30-1, because earning money, like the favorite in The Kentucky Derby, is for suckers.

*Now see Hausler’s Postmortem of the Derby here.