Ways to Win on the Kentucky Derby


Some aspects of the Kentucky Derby are unpredictable: the weather in Louisville is highly variable come the first Saturday in May, and how stiff I want my mint julep changes from year to year.

Others aspects remain constant: tears will flow when My Old Kentucky Home is played; the winner of the Derby will be showered with roses; and there will be a myriad ways to bet on the Super Bowl of horse racing and no end of factors to consider.

I’m here to demystify Derby betting before you “pony up” (so to speak) your hard-earned cash.

The most common ways to bet on the Derby are to pick the horse(s) that will win, place (come in the top-two), and/or show (come in the top three). Those who have accounts at sportsbooks may have even more ways to bet in addition to standard win, place, show, exacta, and trifecta wagering

Those who study the Daily Racing Form will consider many factors when handicapping. These include pace, class, and human connections.

Whether you are an experienced horse racing fan or a novice, it isn’t hard to put together a reasonable opinion, and you can get some action for only two bucks.


Pace handicappers try to envision how the race will be run: which horses will quickly assume the lead, how quick will they run, how much pressure will be on the pace setters, which horses will make their move first, and who does it benefit? A quick pace tends to hurt the horses who are trying to win by going wire-to-wire because they are under pressure for the full mile and a quarter. If your favorite horse is a deep closer, they will need a fast tempo to rally into, and a path to circle the field. Many experts believe you can narrow down a race because, what good is it to bet the secondary pace horse, or the third best closer? You want a horse that is elite at something, whatever their style is.


Those who bet based on class are looking at bloodlines and what horses have done thus far in their careers. Horses who have run against the best of the best and done well are likely to succeed against a large and talented Kentucky Derby field. If a horse’s parents or grandparents are champions, they are more likely to be special on the track. Also, looking at how relatives run at longer distances, at certain tracks, and on various surfaces or weather conditions can help predict what a horse might do on Saturday.

The Human Element

Jockeys and trainers can also impact the race. Among active riders, Gary Stevens, Kent Desormeaux, and Calvin Borel have each won three Kentucky Derbys. Borel’s rail-riding wins aboard Mine That Bird and Super Saver are not only memorable, but largely attributable to his tactics. By a big margin, Javier Castellano has been the best rider in the country this year.

The last 13 editions of the “Run for the Roses” have been won by 13 different trainers. Todd Pletcher, largely regarded as the best in the business, has just one victory all-time. Bob Baffert has guided three horses to the winners circle. Not coincidentally, Pletcher and Baffert are the top two earners this year. Among trainers with a lot of horses who work at primarily major tracks, Steve Asmussen tops the field with 90 wins, while Chad Brown hits at the highest percentage.

Head-to-Head Bets

While the majority of cash wagered on the Kentucky Derby will be placed into large pots via parimutuel wagering, sportsbooks often have prop and head-to-head bets available for big races.

Head-to-head betting is a great way to take advantage of a strong opinion on a horse you don’t think will win. If a 15-1 shot is not your choice to win, but you think is the third or fourth-best horse in a race, you can bet that horse to beat a bunch of other contenders.

Conversely, if you have a negative opinion on one or two horses, you can bet that other horses will beat them in a 1-on-1 match-up. Of course, more than just the two horses race, but if your horse finishes ahead of the contender you dislike, you cash.


Betting on the Kentucky Derby can be a lot of fun because the investment doesn’t have to be great, there are a bundle of different factors you can consider, and there are lots of different ways to put your money down. This Sunday, remember to consider the pace that’s likely to be set, the pedigree of the horse you’re betting on, and the track record of the associated jockey and trainer. Then simply pick how you think that horse will do in the race, as a whole, or against another contender.

Best of luck out there, Derby fans!

(Photo credit: Bill Brine (Flickr: Kentucky Derby 2014-0202) [CC BY 2.0 (http://creativecommons.org/licenses/by/2.0)], via Wikimedia Commons. Photo has been cropped.)

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