How I'm Betting at This Year's Kentucky Derby

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A long-time horseracing fan decides to throw caution to the wind

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Reuters/Matt Sullivan

Horse racing is all about the odds. Well, it's mostly about the odds—some of it is about luck, too. But anybody who works the track or is a part of the industry is invested in making sure that you never believe that. And convincing you, the bettor, probably isn't very difficult; everybody who might be throwing down their weekly wages on the horses wants to feel like they can analyze the numbers and position themselves above the rest of the pack. You want to walk into the park absolutely convinced that you'll walk out with a fatter wallet. And you'll think that big wad of cash is even heavier, even more special, if you feel like you've earned it.

But you can only have so much fun if your nose is in the books the entire time you're sitting at the track. Preparing to attend the $2 million Kentucky Derby at Churchill Downs, I waited anxiously for the Wednesday afternoon lottery that would determine the horses—and their pole positions—that would make this year's field. As soon as the horses were chosen, I put aside some of my work and starting to dig into the statistics. But then I stopped. This will be my first time at the Derby and I'm going to this race for the spectacle and the experience—the rarefied gentry; the floppy, wide-brimmed hats; the seersucker suits—as opposed to one more chance to win some money. When I make my way to Louisville this weekend, I'm going to get drunk. So, taking a cue from my mom's lazy approach to gambling, I've devised a foolproof strategy that relies, for the most part, on luck, but adds just a hint of odds analysis. I'm only betting on two horses, those with the ideal pole positions. It's a strategy I plan to stick to so that, if I have a few too many mint juleps, I won't return to D.C. in debt, hundreds of useless tickets in my suitcase. And if I win? I'll claim it was all because of a couple of smart choices. Luck? Pft.

Story continues after the gallery of the 20 horses in this year's Kentucky Derby field.

When the pre-lottery favorite, Dialed In, drew the No. 8 pole, several sports websites cheered the position. "This isn't picking teams or bidding on starting positions," according to SB Nation. "It's simply hoping to see your number pulled in a position near the middle." No. 8 out of 20 is pretty close to the middle and Brian Floyd called the draw "excellent." The thinking is that, if you're too far on the outside of the pack, you'll never be able to find your way to the rail for the finish; and, if you're stuck starting near the rail, you'll be crushed and slowed down as 19 other horses invade your space. But a little bit of research challenges that argument. Over the long history of the Derby, positions 1 and 5 have produced the most winners with 12 each.

I'm putting my money on Archarcharch and Decisive Moment.

Currently at the top of his game, Archarcharch is a three-time stakes winner with a 6-3-1-1 record. He beat Nehro, another Kentucky Derby competitor, in the Arkansas Derby, his last prep leading up to the big race. Unfortunately, Jinks Fires, the horse's trainer, isn't happy with the pole position. "Not a good place to be," he told the Daily Racing Form. "I've never liked the one hole, but you got to do what you got to do." And you can be sure that Archaracharach's team, which also includes owners Robert and Loval Yagos and Grapestock LLC, will do just that. Fires has been waiting 50 years to get a horse, literally, in the race—and his, well, fire is clear. Archaracharch was one of the few horses training on the track this past Tuesday when the temperatures were low and the track wet. Despite complaints that this year has one of the slowest fields in recent Derby history, Archarcharch was running at 52 seconds per half-mile in the rain.

The first horse to arrive at Churchill Downs to begin workouts in preparation for Saturday's race, Decisive Moment is putting in extra hours to make up for his long odds; at 30 to 1 on the morning line, Decisive Moment is second-worst only to Watch Me Go, who is stuck all the way on the outside of the pack. But the team—Kerwin Clark in the saddle; Juan Arias training and Ruben Sierra, an owner who has been obsessed with the race ever since Cannonero II won the 1971 Derby the year he came to the United States as a six-year-old Venezuelan, offering guidance—is committed. "He's always on his horses," Sierra told a reporter from the the Kansas City Star of Arias, who has been riding Decisive Moment at Churchill Downs since late March. "I like everything about him," Arias said of his horse. "He's got good composure, good personality, and he's got ability. It is a wide-open race. He's the type of horse that goes out and tries every time. No matter how the race shapes up, he's always there to try."

Good enough for me.

Back when I lived in Chicago, I would take the train out to the suburbs to visit Arlington Park, the nearest track, with some frequency. Whenever my mom decided to accompany me, I would spend hours at a stand-up table, chewing on my red pen as I my eyes darted from one program to the next. She'd stand across from me, chatting and slurping on a Diet Pepsi. As I jotted down facts and figures—breeder, owner, sire, trainer—she'd go on and on about how her two aunts still weren't on speaking terms. Jockey, past odds, age, blinders. Once I had digested it all, I'd make my way to one of the automatic betting machines and feed a few $20s in. Tickets would spit out, at least a half-dozen per race, a half-dozen that would later be torn up and tossed into one of the trash cans that line the shameful walk leading from the fence that follows the dirt track to the betting machines, where another field of horses is always waiting.

I'm only 23 years old, but I've been playing the horses since before I could reach the touchscreen that allows you to place your bets. Over the past nine years or so, I've come out ahead, winning hundreds of dollars at a time on multiple occasions. But I haven't won so much as to make all of those hours spent in the books worth my time. I've always been a little bit envious of my mom's ability to throw her money at horses because they had a funny name or because the jockey was wearing a color she adored. I've always been a little bit envious of the rowdy frat bots who were on their third beer by the second race. This weekend, I will take a less mathematical approach to my game; I will throw caution to the wind, have some fun and see how it turns out. I'm hoping for a little bit of luck.

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Nicholas Jackson is a former associate editor at The Atlantic.

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