The Beginners Guide to Betting on the Kentucky Derby

Let Maxim and the folks at show you how to make the 140th Run for the Roses the most memorable one ever.

Betting on the Kentucky Derby is a no-lose proposition. What? Think about it. Derby day falls squarely in the sweet spot of spring. Classy women in the grandstand and at parties everywhere don crazy hats and colorful décolleté dresses. You’re more than entitled to muddle and mix up a happy hour pitcher of delicious mint juleps for you and your friends. And with 20 of the blazingest Thoroughbreds on the planet bursting out of the gate at about 6 p.m. eastern on May 3rd, the Most Exciting Two Minutes in Sports is absolutely guaranteed to provide ample thrills, heartbreak…and substantial payouts.

Fortunately, you don’t have to be a seasoned railbird—or know how to decipher the arcane data in the racing forms—to give yourself a decent chance at hitting the board at Churchill Downs. Hell, you don’t even need to drive to the nearest track or queue up with the grumpy old dogs at the local OTB.

At—now open for business in 38 states—you can set up an online account in minutes, with as little as a few bucks, and then place your Derby wagers from the comfort of your living room right up to post time…while enjoying that julep. The account is free, and TwinSpires will even throw you a $100 credit to get you started.

Now, about the wagering. With the help of expert handicapper Ed DeRosa of, the official online betting partner of the Kentucky Derby, we’ve created a handy primer on the wide variety of wagers and betting strategies that can boost your odds to cash in on the Run for the Roses. “When I talk to someone who’s new to horse racing, I tell them the two extremes when it comes to betting. There’s win wagering, on one side, and superfecta wagering on the other, where you have to pick the top four finishers in the race. It’s tough to pick, but the payouts are huge.” Here’s a bit about those wagers and everything in between.

One-Horse Bets

Win: Everything pays pretty well at the Derby, partly because there are so many horses. “Last year the favorite, Orb, won, and it still paid $12.80 on a $2 bet,” DeRosa points out. So if you really love a certain horse, keep it simple and play it to win. A $10 win wager on Orb and you would have walked away $54 to the good. And don’t be afraid to try out a long shot. Twice in the past nine years, the winner paid in excess of $100 on a $2 bet (Giacomo, 2005; Mine That Bird, 2009)

Tip: If you’ve never placed a wager before, remember to play the horse by the number, not the name.

Place, Show: It can be pretty hard to pick the Derby winner. Playing a horse to place or show allows you to hedge a little and still earn some decent cash. (A place bet pays if your horse finishes at least second; show pays for at least a third-place finish.) How decent? Last year 34-1 shot Golden Soul sneaked up in the stretch to take second and paid a healthy $38.60 on a $2 bet. His show money ($19.40) wasn’t too shabby, either.

Across the Board: Playing a horse across the board means you wager for win, place, and show, three separate bets. If the horse just finishes third, you’ll usually get your money back and sometimes better. If the horse wins, you get all three payouts. For instance, the 2011 winner, Animal Kingdom, paid $43.80/$19.60/$13, so if you played him across the board for $2 (a $6 wager) you got $76.40.

Exotic Bets

Exacta: To hit an exacta, you have to pick the two top finishers – not the easiest thing to do out of a field of 20. But the upside? Last year’s exacta paid $981.60 for $2. For the same two bucks, you can play a $1 exacta box, where you pick the top two finishers, but they can come in in either order. With a box wager, you only get half the payout, but your odds are better.

Trifecta: For this bet you have to pick the top three finishers. At the Derby, you can play a trifecta with as little as 50¢. Last year if you hit that wager it was good for a cool $1,731.40. You can also box a 50¢ trifecta for a total of $3. Then you’d get paid regardless of the order if you picked the top three horses. Trifectas are still harder to hit, but so tantalizing, and the average payout over the past decade has been about $2,000 on a buck. Maybe you want to pick a couple of favorites and throw one long shot in the mix. That was the recipe for last year’s trifecta.

Superfecta: If you really want to shoot for the stars, try picking the top four horses. It gets a bit in the land of the lottery, but you can play a handful of superfectas for a total of five bucks, and if you catch lightning in a bottle, you could be shopping for a Mercedes. Three times in the last nine years, the score for a dollar superfecta reached six figures. In 2005, 10-18-12-17 paid in excess of $432,000. Are any of those your lucky number?


You have a few days left, so you have a chance to do a little research and see how the wise guys are playing it. For the latest trends and breaking developments with the field—see which horses did bullet work in their training runs, whatever that means—pay a visit to’s The Handicapper’s Edge newsletter. And check out Derosa’s Blog while you’re there for tips and insights.

Feeling a little more, uh, intuitive? Nothing wrong with that. Some people like to bet their birthday. If you’re birthday is October 18, you can play a 10-18 exacta each year. That number was good for four grand in 2005. Maybe you take a fancy to a certain horse’s name. This year Wicked Strong, with its reference to Boston standing strong after the marathon bombing, should be a sentimental favorite.

Or, if you’re going for the girl power, Rosie Napravnik will be aboard Vicar’s in Trouble at long odds bidding to become the first female jockey to win the Derby. There’s no wrong bet. Just make sure you keep it in your budget!

And however you decide to play the race, be sure enjoy Derby Day, one of the greatest events on the American sports calendar.

See you in the winner’s circle.

Photos by Photo: John Gress / Rueters / Lanov