By Kevin Martin

The Kentucky Derby is a difficult race to handicap and bet. The most popular horse race in America includes a huge field of twenty three-year-old colts, most with less than ten career races, running a distance they have never run before in front of the largest and loudest crowd they will ever see. Add to that the unpredictability that comes with any horse race and the logical play is not a play at all. However, few that bet on horse racing – from the casual to avid horseplayer – can pass up placing a wager on the Kentucky Derby.

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The $100 Bet

I’ll put $40 on Dortmund’s nose to win. He has yet to lose and it’s hard to find a fault with the son of 2008 Kentucky Derby winner Big Brown. He has shown versatility in running on the lead and winning from off the pace. He looked great in winning his lone start at Churchill Downs last year. He has had to overcome adversity in his six race career, coming back after being passed in the stretch to win the Robert Lewis Stakes earlier this year. His jockey, Martin Garcia, has won big races including the 2010 Preakness and the 2014 Breeders Cup Classic. At odds that could hover around 4-1 come post time, Dortmund is a sound investment in the win pool.

Along with playing him to win, I will key Dortmund on top of a trifecta with seven horses underneath to fill out the second and third positions. Only in the Kentucky Derby can such a bet be considered prudent or even sane. Boxing seven horses under a favorite is not a common tactic but the trifecta pool in the Derby routinely pays over $1000 on a $1 bet. There are many ways to play trifecta but i’m going to take a stand in the win slot with Dortmund so I can spread wide underneath where I will include favorites American Pharoah and Carpe Diem as well as colts that will likely be 15-1 or greater in Upstart, El Kabeir, Bolo, International Star, and Firing Line. To win on this play, Dortmund must finish first and the second and third place finishers must come from the seven on my ticket.

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I will hedge slightly with a three horse trifecta box with my top three choices in the race in Dortmund, American Pharoah, and Firing Line. If those three finish in the top three in any order, I would cash in on that ticket. It’s not terribly creative using the likely top two choices in American Pharoah and Dortmund but barring a bad trip — always a possibility in the Derby — they should be among the top three when they hit the wire. Firing Line has run within a head of Dortmund in two starts and crushed an overmatched Sunland Derby field in his last start. He will have a determined jockey in Gary Stevens, the 52-year-old Hall of Fame rider seeking his fourth Kentucky Derby win.

When betting the Derby, you have to take a stand against colts that some very sharp handicappers will pick to win. None of the three that follow would surprise should they win but you can’t bet them all. I will take a stand against Materiality, Frosted, and Mubtaahij. Materiality ran great in the Florida Derby but, with just three career races, I think his inexperience catches up with him this Saturday. Frosted ran the race of his career in the Wood Memorial but he has shown enough inconsistency in his career to make him a play against. Mubtaahij has seemingly divided handicappers into two camps – those that love him and those that don’t. I don’t. He won the UAE Derby in Dubai in an impressive performance but there are significant differences between racing in Dubai and the U.S. No UAE Derby winner has come close to winning the Kentucky Derby and I feel confident in betting against him.

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How to Place the Bet

When it comes to placing the wagers proposed here, it requires some knowledge in the language of betting on horse races. When placing a bet, you need to use the track name, race number, type and amount of the bet, and the program number(s) for the horse(s) you are playing.

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The first one is easy, a $40 win bet on Dortmund would sounds like this:

“Churchill Downs race 11, $40 to win on the 8.” (The Kentucky Derby is the 11th race at Churchill Downs on Saturday.)

To box Dortmund, American Pharoah, and Firing Line in a trifecta, ask for the following:

“Churchill Downs race 11, $2 trifecta box on the 8, 10 and 18.”

The above includes six combinations. On a $2 bet the total cost will be $12 (6 x $2).

The bet where we key Dortmund over seven other horses is a trifecta key bet. The key horse is Dortmund in the win position with seven horses in both the second and third position. Ask for the bet as follows:

“Churchill Downs race 11. $1 trifecta key. The 8 over the 2, 7, 9, 10, 12, 18, and 19.” The total cost of this bet is $42. (There are 42 combinations, so for a dollar it costs $42.)

The total cost of these three bets is $94. That leaves us $6 for a beer or, if we are at Belmont Park in New York, a down payment on a beer.

Good luck!

Of course, its more fun to make your own picks, you can learn do that at Hello Race Fans. You can also see a rundown of all the starters with their annual Kentucky Derby Cheat Sheet.

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Kevin Martin is the founder of the thoroughbred racing history site Colin’s Ghost and a contributing editor at Hello Race Fans