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The 2011 Kentucky Derby produced a $3,952 trifecta payout for a $2 bet when Animal Kingdom prevailed over runner-up Nehro and third-place finisher Mucho Macho Man. (Photo courtesy of Eclipse Sportswire)

Choosing a Kentucky Derby horse among the 20 entries is no easy task. But it’s only half the battle. Much more difficult is figuring out the best way to bet the race to make some real money.

What’s that? You were just planning to bet your pick to win and be done with it? That’s fine, but you’re missing out on a rare-and-exceptional betting opportunity!

The Kentucky Derby is the most wagered-on sporting event in the United States. Even more money than is wagered on the Super Bowl gets bet on the Kentucky Derby! And a lot of that money goes into exotic pools, meaning higher-than-usual payouts – even when a heavy favorite finishes in the money!

Let’s look at the average and median payouts for the win bet versus the exotic bets over the last ten years.



















Still want to invest your whole bankroll into win bets? 

These amounts are skewed a bit by $100+ longshot winners. But there have been two of them in the last 10 years! It isn’t that uncommon in a huge field where the money isn’t very evenly distributed among horses. So it’s important to consider the averages, but I also included the median just to be fair.

So then how to bet? It’s tempting to say, “let’s play the super!” Those are some huge numbers. But keep in mind that the superfecta (choosing the correct order of the first four horses) is not only hard to hit, it’s very expensive to bet. Boxing 5 horses for $2 is $240. Boxing 6 is $720.

A much more economical way to try for a huge payday is to play the trifecta. The trifecta is easier to hit (you need to choose the correct order of the first three horses) and requires a substantially lower investment. Boxing 5 horses for $2 is $120. Boxing 6 is $240. Boxing 4 is only $48. 

What’s more is you can bet trifectas for as low as $.50, meaning you can cut these numbers by three-quarters. This also cuts your payoff should you hit, but a quarter of $19,000 is still a pretty good payoff for a $30 bet!


09Derby Inside

Photo courtesy of Eclipse Sportswire

If you want to add more horses but don’t want to pay exponentially higher prices, consider ranking your horses. 

Playing 8 horses in the trifecta by boxing them for $2 = $672

Or you could break those 8 horses into three categories: your top picks, your “wouldn’t be surprised” picks, and your honorable mentions. You should make sure that there are some live longshots in at least the honorable mentions, but probably your second choices as well. Then structure your ticket this way:

Top picks: 1,2

Wouldn’t be surprised: 3,4,5

Honorable mentions: 6,7,8 

1,2 / 1,2,3,4,5 / 1,2,3,4,5,6,7,8 = 48 combinations = $96

Even if you chose to expand it to 9 by adding another top pick your bet would only increase to $210. (1,2,3 / 1,2,3,4,5,6 / 1,2,3,4,5,6,7,8,9 = 105 combinations) Compare that with $1,008 to box 9 horses in the trifecta!! 

Obviously you can play with the structure to find the bet that works for your bankroll and the confidence (or lack thereof) you have in your selections. Having more horses in the top spot makes the bet more expensive, but makes it easier to hit. 

Of course you may only have $100 to bet on the race. Fine. Play the trifecta for $1 or even $.50.

Or, if you’d rather, put the whole $100 to win on your favorite horse and root him home. At an average of $41, you could be taking home thousands of dollars! Or you could be kicking yourself. In 2008 when Big Brown won the race as a huge favorite he paid $6.80 to win. The trifecta that year, very hittable with a solid “wouldn’t be surprised” horse Eight Belles running second, paid $3,445.00. 

I don’t normally play trifectas, but on Derby day this is how I’ll invest most of my money. However you choose to invest yours, I wish you luck. And Happy Derby!


Hill Mt BInside -Eclipse

Photo courtesy of Eclipse Sportswire

Image Description

David Hill

David Hill is a writer, an agitator, a comedian and a gambler. He grew up in Hot Springs, Arkansas near the Oaklawn Park. Today he lives in New York City. Further reading at

Image Description

David Hill

David Hill is a writer, an agitator, a comedian and a gambler. He grew up in Hot Springs, Arkansas near the Oaklawn Park. Today he lives in New York City. Further reading at

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