Zen Betting The Roses: A Kentucky Derby Preview for Beginning Betters

Pete Hausler


There’s this, like, lattice o’ coincidence that lays on top o’ everything. Give you an example: suppose you’re thinkin’ about a plate o’ shrimp. Suddenly someone’ll say, like, plate, or shrimp, or plate o’ shrimp out of the blue, no explanation. No point in lookin’ for one, either. It’s all part of a cosmic unconciousness.

—Miller (Tracey Walter), Repo Man

There’s an old saying around the racetrack: White snows in March, bet the white silks in May. Since there was an inordinate amount of snow this winter in many parts of this great land, and since there is an equally inordinate number of jockeys who will be sporting white-colored silks (the uniform jockeys wear, representing the horse’s owner) in Saturday’s 134th running of the Kentucky Derby Presented by Yum! Brands (henceforth to be referred to as the Derby), it seems like a good year to put this adage to use.

Erm, ah, seriously? I’m kidding. I made that up. There is no adage equating snowy Marches to white silks in the Derby. But I made up this little white lie to make a point: it’s fun to bet the Kentucky Derby, probably the only horse race which busts out from its usual rear-of-the-sports-pages home, to burst into the public consciousness for a week. Even if you know nothing about horseracing, why not make up a saying of your own and go with it? If you want to weed through printed website pages of Byzantine turf data and jargon-laced “professional” analysis that would probably—literally—stretch to the moon, go right ahead. If you want to have a little fun handicapping this year’s race, read on.

Horserace handicapping—picking winners—is not an easy game. I got hooked about ten years ago, partly because one of my old friends—we’ll call him Mr. Joe from N.O.—did it for a living. It took me a full year of intense daily study, obsessive notebook-keeping, nerdy newspaper clipping, and dozens of phone calls to Mr. Joe, to understand the intricacies. I’m not necessarily saying I’m good at picking winners, just that I know what to look for on the stat sheets (usually called the racing form).

One problem is the veritable mountain of stats. If you come to horseracing cold, like I did, it’s hard to figure out the nuanced difference between a Beyer speed figure and track variant. Or if a 21-and-two-fifths seconds in the first quarter is blazing, average, or plodding (it’s blazing). Another part of the problem: if a horse, trainer, or jockey, in their career, wins even a mere 25% of their races, that’s considered stupendous. So how are we semi- or unenlightened pikers supposed to guess who is going to win a race, when one in four is considered tip-top? Imagine if a baseball team went 40-122 for the season!

Picking winners is all about subtraction; you just throw out the horses you don’t like. Sounds easy. Problem is, the longer you look at the form, all the horses start to look bad. Or worse, they all start to look good. Sometimes the subtraction process can be abetted by—call it what you will—tuning into the cosmic unconsciousness, a la Repo Man (see epigraph above); or using The Force (no explanation necessary); or by employing something I like to call Zen-betting.

Zen-betting refers to any time I make a bet where I haven’t previously pored over the racing form or even the entries in the sports pages (which give bare-bones information like jockey/trainer combination and brief analysis). Zen-betting started for me, rather circumstantially, five years ago, after my first daughter was born. Basically, I had less free time to read the racing form, and increasingly less money to fritter away on betting. But, more, it was the time thing.

In my early years of The Obsession, i.e., before kids, I had essentially boundless amounts of time. Every night, I could intently comb the racing form; Saturdays dawned as empty days just crying out to be filled, which I was more than happy to do by schlepping out to my local tracks—Belmont (classy) or Aqueduct (no comment)—or visiting one of New York City’s fine off-track betting establishments. When the free time disappeared, that’s when I turned to the free-association method of Zen-betting.

As embarrassing as it is to admit this, I’ve had almost as much success with Zen-betting as informed betting. Zen-betting appears in many incarnations: plucking numbers (you always bet horses by their program number, not their name) out of the ether; choosing, as a lottery player would, personally significant numbers, like your kid’s birthday; circling a name you like, or that nags at you (sometimes the universe attempts to whisper to you); or pairing horses via some sort of name connection—like, if there just happen to be two horses in a race named for, oh, I don’t know, writers with one-syllable.

In an ongoing, pre-Derby email parley with the abovementioned Mr. Joe from N.O., we discussed this notion of Zen-betting. The occasional foray into some sort of hunch or cosmic betting is a topic we’ve bandied about over the years. His experience in handicapping goes much farther back, and his knowledge of the game is far deeper than mine. Not surprisingly, he has many stories of either successful Zen-betting forays or times when he kicked himself for not taking the cosmic plunge. To wit, the man himself says, “One time I left Keats and Yeats at 50-1 out of a trifecta [this so-called exotic bet picks the first three finishers in a race]. A [writer’s] trifecta [with] 50-1 horses? Yet I did it. I left out Keats and Yeats, for Christ’s sake.” Keats and Yeats indeed finished in the top three, sending the trifecta payment out the roof.

In the last few months, I’ve walked into the OTB, and three times have hit trifectas on sheer luck. One time I was walking and said, the next three numbers I see, I’m boxing in a trifecta. They were 7-8-9, I bet the next race running on the simulcast in the John Street OTB in lower Manhattan, and they hit. It paid over $300. I’m not saying this happens every time, but it feels good when it does, heading back to work $300 richer.

But just as many, or more, get away from you. You’re given the sign, and don’t act on it. A few weeks ago, I was watching American Idol, the one where Andrew Lloyd Webber is the mentor, and he did this odd thing. He commented on the eyes of two consecutive contestants. First, he said something about Irish eyes smiling (to the now-booted Carly) and then shortly thereafter, to the next contestant, something about how the eyes have it. I don’t know why I found it striking, I guess the repetition of “eyes” made it stick out, and I wondered what it is with Webber and his eye obsession. The next day, I was looking at the Aqueduct entries in the paper and there was a horse in one of the late races, Them There Eyes. I saw it; I remembered Webber’s eyes comments. I passed, bet another horse. Them There Eyes won at 7-2 odds.

But let’s get specific here. The Derby is its own special challenge. I don’t think there’s a single race, game, match, tournament, etc. in all of sports that has a longer lead-up for one single afternoon. And it’s a short afternoon, at that, the race lasts just north of two minutes (you’ve heard the slogan, the most exciting two minutes in sports). Semi-officially, the so-called Derby Trail begins on January 1, though you could argue that it actually begins the previous autumn, when the cream-of-the-crop 2-year olds are scrutinized with an eye toward next May. (The Derby is for 3-year-olds only. Horses get one and only one shot at winning).

Looking at this year’s crop of Derby entries, it’s the perfect year to try out some Zen-betting. There are a lot of decent horses and one standout—the possible monster, Big Brown—but all of them have flaws. The 20 horses entered, as of deadline, are kind of like that Whitman’s Sampler box, where the chocolates all look really good in their pristine condition, but when you bite into them, they’re filled with old and not-quite-identifiable citrus whip. If you look too closely, there’s something not to like about all of them, even Big Brown (a history of bad hooves).

So, without further ado, here are six Zen-betting strategies to consider for this Saturday’s Derby. Most of these scenarios will cost you under $10, and of course, you can do a win bet at the OTB for as little as $2. When you have something riding on a race, even a couple dollars, it makes watching 100 times more exciting. Good luck.

1. Bet the White Silks.
Seriously. There are currently seven horses entered in the Derby field whose jockey’s primary color will be white: Tale of Ekati, Colonel John, Gayego, Big Brown, Court Vision, Cowboy Cal, and the filly Eight Belles. It doesn’t hurt that this group contains probably the top three contenders (Brown, Colonel, and Ekati) and the other four have a legitimate shot to win, and should be considered live longshots. Why am I harping on the randomness of the white silk thing? Because it’s unusual to see so many in the Derby, there are usually one or two, not seven. I think the universe is trying to tell us something. Box up some combination of these in an exacta (a bet that picks the first two finishers in the race), or bet one of them to win. (Remember, bet the horse’s post number, which you can find in your local sports pages.)

2. Bet the Z pair.
There are two similarly named horses, owned by the same outfit: Z Humor and Z Fortune. A $2 exacta box will cost you $4, and if these two hit first and second, it would be a very nice return on investment, as they are both longshots.

3. Bet the gorgeous grays.
The rarest color for a thoroughbred is gray. Most horses are brown like a brown shoe, or chestnut. There are three grays entered this year: Monba, Z Fortune, and the above-mentioned filly, Eight Belles. Monba happens to be trained by one of the top three horseman in the U.S., Todd Pletcher. Monba also has the same sire (daddy) as Monarchos, another gray, who won the Derby in 2001. Box up these three in a trifecta, or bet one of them to win.

4. Bet the “Rudy” horse.
That’s Rudy, the cinematic love note to Notre Dame football, not erstwhile GOP candidate and 9-11 exploiter extraordinaire Rudy Giuliani. Every year there is a feel good story. Either the horse or the trainer or the jockey has done something to tug at the heartstrings. I say this in all earnestness, this is what makes sports worth following, the behind-the-scenes stories. This year’s Rudy is Smooth Air because of his trainer, Bernie Stutts. The Florida-based trainer is 70 years old, and in 40 years of training, this is his first Derby starter. Stutts himself likens his situation to “the third string quarterback that is starting the Super Bowl.” Realistically, the horse is a longshot, and Smooth Air didn’t help his chances by spiking a fever early this week. But if he crosses the wire, get set for the media to crank up their schmaltz-meter to 11.

5. Bet the plate o’ shrimp.
When the universe throws you a name, ignore at your own peril. Yesterday, I received a monthly newsletter from the online rare and used book retailer Abe Books. I love Abe Books, and because I browse their site so often, I rarely, if ever, open the monthly newsletter. Something made me open it yesterday, and to my shock, a 2008 Derby horse name was staring me right in the face. Abe was touting the sale of limited issues of a rare and valuable arts and culture magazine called (pause for effect) Visionaire. Chills. Visionaire the racehorse is in my bets now. He has to be.

6. Bet your favorite name.
Pick a name, any name, read through the list of twenty starters, and choose one that sings out to you. Employ your kids in this task; I always read the names to my daughters, and put a fiver on each one they pick. This year, my favorite horse-name is Denis of Cork. I don’t know why I love this name so much. There’s something charming about horses with simple people names (a few years back, one of my faves was David.) Plus, I like saying this: How can you not love a horse named Denis? And to top it off, he’s from Cork!

Good luck and good betting. Remember, when you’re at the betting window, no second guessing. And don’t bet the mortgage.

Pete Hausler edits nonfiction for Post Road magazine, is a contributing editor to Field: New Sports Journal, and writes book reviews for a large, daily financial newspaper. He lives in Brooklyn, N.Y. and Milanville, PA with his wife, two daughters, and a dog named Boo. He is (and forever shall be) working on a bar memoir.