Dandy at the Derby 5-1-2013

A Gentleman’s Wager

A guide to betting on the ponies

Kentucky is known for two things, Bourbon and Horses. And on one glorious day each year these two American pleasures collide in the most exiting two-minutes in sports – the Kentucky Derby. Of Rogues and Gentlemen has covered the Run for the Roses from the sartorial perspective, but the Derby isn’t all seersucker and mint juleps.  Horse racing is a betting man’s game, a mix of skill and luck that necessitates ponying up a few sawbucks to test one’s relationship with that fickle mistress, chance.

The Basics

If this is your first time at the betting window, you may want to keep it simple. Pick a single horse and bet on him coming in first, second or third.

Win – Betting to “Win” means exactly what it sounds like, you’re betting that your chosen horse will cross the finish line first.

Place – Betting on your horse to “Place” means you believe your pony will come in first or second.  Obviously, hedging your bet this way reduces your potential winnings.

Show – As you may have surmised, betting to “show” spreads your bet on a single horse across the first, second and third placements.  If your horse finishes anywhere in the first three positions you will win back your money and a little more.

Mix and Match

Betting in combinations dramatically decreases your chances of winning. But, like in all things, the greater the risk the sweeter the reward.

Exacta – Betting the exacta requires you to choose the first and second place horses, in correct order.

Trifecta – You must pick the correct order of the first, second and third place horses.   This takes a little know-how and a lot of luck, but the payoff is astonishing.  In the 2005 Derby a $2 trifecta bet paid off a whopping $133,134.80.

Superfecta – This requires an expert knowledge of the horses, the track conditions, the jockeys and the trainer. You must correctly pick the first, second, third and fourth place horses. Probably best left to the professional gambler.


So, this Saturday, place a few bets and see how you fair.

And remember, a fool and his money are soon parted.

TAGS: Betting | Brooks Brothers | Horses | Kentucky Derby | Mint Julep | Run for the Roses | Will Rogers

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