Sports News Without Fear, Favor or Compromise
Sports News Without Fear, Favor or Compromise

Let's All Get Filthy Rich Betting On The Kentucky Derby

Illustration for article titled Lets All Get Filthy Rich Betting On The Kentucky Derby

The Kentucky Derby, a/k/a “The Fastest Two Minutes in Sports,” is an event rich with tradition. It’s an opportune time to brush up on your Hunter S. Thompson, and/or drink cheap bourbon out of silver cups, and/or laugh along with rich assholes who give their horses ridiculous names for their own amusement.

It is also an incredible excuse to eat meat cooked in the sun, find a dead body or two, and gamble your balls off. I’d love to tell you I’m not bragging here—I clearly am—but I’ve picked three of the last four Derby winners correctly, and only whiffed last year on California Chrome out of pure unadulterated hubris.


If, like me, you suffer from an excess of unearned confidence, there are a few ways to get your betting fix in. Racetracks, casinos, and OTB parlors are usually legit, though laws vary by state. You can also look online, either in the same place you bet on the Super Bowl or the Derby’s official online partner. Finally, you’ve got friends and relatives with bookies—ask them nicely.

Don’t forget these, though.

The Three Big Rules Of Gambling

1. Never bet anything you can’t afford to lose. This one is obvious, right? I mean, pretty much all organized gambling is designed for the majority of people to walk out with less money than when they walked in. If that wasn’t the case, places like Goldman Sachs would go to casinos, instead of just acting like them (ZING!).


2. Quit while you’re ahead. This doesn’t really apply for the Derby, as it’s only one race, so if you lose, you’re fucked, and if you win, you’re golden. But it works for roulette, or at least you’ll realize it works only after you don’t do it. Especially at Harrah’s in New Orleans. Jazz is a lot sadder when you’ve given back a month of free rent. I digress.

3. Never listen to anyone else. You’re going to be tempted to listen to your blowhard friends who tell you to bet on the “mudder” or the “rail runners” or “that scratched horse.” Their advice is usually useless, and if you follow it, your original choice will win. Your fault for listening. (Side note: If you don’t follow their advice, their choice will win. And if they ask you for money for picks, look at them with sorrowful eyes and walk away.)

Bet Crazy Shit

Let’s talk about types of bets. First are your single-horse bets: WIN, PLACE, and SHOW. Bet on a horse to WIN, and if he wins, so do you. Simple enough. PLACE is like a win, except if your horse is First Loser, you’re still a winner. Bueno. Finally, you can bet on a horse to SHOW; if your horse is top three, you’ve got a winning ticket


Single-horse bets are fun and rah-rah and “Huzzah, Dortmund, quick to victory!” but they provide none of the filthy, balls-deep degenerative-gambling thrills and satisfaction of the exotic bets: the ‘fectas. The exacta (a/k/a perfecta), trifecta, and superfecta are the greatest bets. They are what you would bet if you got a sports almanac from the future and had to start your fortune with what you found in your couch. For an exacta, you have to pick the first two finishing horses, in order. A trifecta is the first three; a superfecta, the first four. You can also make these bets “boxes,” where you pick the same horses in every combination.

The order is key. In 2014, a year in which the heavy favorite won, a $2 exacta would have net you $340. In 2013, a relatively staid year, a $2 trifecta would have won you $6,900. In 2005, a bonkers year, a $2 superfecta would have net you just over $1.7 million. Those are big hits for a reason. Horse odds aside, your chances of picking three consecutive random numbers out of 20 is around 1 in 6,500.


But Bet Crazy Shit Strategically

I should note that “strategy” is an incredibly loose term here. Advanced statistics are a lot tougher for an animal-based sporting event held once a year with mostly new participants. You’re basically trying to parse a gorilla’s WAR on Opening Day of a 20-team Gorilla Baseball League where every gorilla is his own team and they all play at once. (Note to the networks: would watch.)


That said, four times in the last eight years, the favorite has won: California Chrome in 2014, Orb in 2013, Big Brown in 2008, and Street Sense in 2007. That doesn’t mean it’s a 50-50 bet, but a couple dollars on the favorite is a decent hedge against a fistful of weird trifectas.

Next, bet a fistful of weird trifectas. Long odds be damned, you’re buying lottery tickets where the drawing is held by tiny, dehydrated-to-the-point-of-near-mummification speed freaks whipping the shit out of enormous meat robots bred for nothing but two minutes of win-or-die speed. If that doesn’t do it for you, stay home and drink milk.


Last, bet one superfecta. Just one. It’s two dollars. Use numbers that matter to you, like an old address, or a locker combination, or your mother’s Social Security number.

Wait, Who’s Running This Year Again?

Post odds are likely to change, but the runaway favorite early is American Pharoah, coming in at 2-1. Fourth in points but second in winnings leading up to the Derby, he has three quality wins, and is being trained by Bob Baffert and ridden by Victor Espinoza, both past Derby winners who know what they’re doing.


Dortmund, who opened at 9-2, is another Baffert horse and the son of 2008 Derby winner Big Brown, who was a cracked hoof away from winning the Triple Crown. I like Dortmund a lot, but since I’m putting that in print, he will finish dead last after trampling an errant orphan.

Carpe Diem opened third in the odds on the back of a strong win at the Blue Grass and is being ridden by John Velasquez, a Derby veteran and 2011 Champion.


Also, not to be slept on are International Star at 25-1 and Materiality at 14-1. International Star was first in points in the Road to the Derby, but against weaker competition, and Materiality won the Florida Derby, a race that has picked its share of Derby champions.

Obviously there are other horses, but that’s enough to get you started if you’re lazy.


And They’re Off!

I Won!

Holy shit, really? Way to go. I’m assuming that you are now fabulously rich. The first thing you’re going to want to do is put your ticket someplace EXTREMELY FUCKING SAFE. God help you if you blow this for us. See any big losing tickets on the ground? Grab them. Gambling losses count against gambling winnings on Tax Day. If you mix up the winner in your hand and the losers on the ground, you will talk about it on your deathbed, where I will put you. Which means, among other things, that you’ll miss the Preakness.


Samuel Wadhams grew up hard in Vermont and now grows soft in New York. He is not an expert on anything. Occasionally, he tweets here.


Art by Sam Woolley.

Adequate Man is Deadspin’s new self-improvement blog, dedicated to making you just good enough at everything. Suggestions for future topics are welcome below.

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