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How to Bet the 2021 Kentucky Derby

Churchill Downs

Churchill Downs

Jamie Rhodes-USA TODAY Sports

The Kentucky Derby is a horse race unlike any other in the United States, as a field of 20 three-year-olds will attempt to navigate the mile-and-one-quarter distance at Churchill Downs in Louisville, Kentucky this Saturday. Not only is the Derby the most famous horse race in the United States (and arguably the world), but it also presents one of the best wagering opportunities throughout the entire year in all of sports. The combination of twenty young, inexperienced horses running a demanding distance can lead to wild results - and wild results can produce potentially life-changing scores from a betting perspective. Opinions on how to bet the Kentucky Derby vary depending on who one is speaking with, but the beauty of betting the Derby - and horse racing, in general - is the ability to make a wager as simple or as complicated as the gambler would like to.

The most straightforward wager in all of horse racing is a bet to win. Simply put: if the horse you bet on to win the race wins the race, you cash your ticket. In most cases, cashing a win-mutuel is not going to lead to any sort of life-altering score, but because of the large number of entrants in the Kentucky Derby field, even betting the favorite to win can return a reasonable sum of money. Over the course of the past ten years, winners of the Kentucky Derby have paid the following amounts on a $2 wager: $43.80, $32.60, $12.80, $7.00, $7.80, $6.60, $11.40, $7.80, $132.40 (via disqualification), and $18.80.

Two wagers that are in the same family as the win bet are place and show bets. To cash a place bet, the horse you bet to place must finish either first or second; if they do, you cash your ticket. The same goes for a show bet, however we are now talking about having a horse finish first, second or third for a show wager to be cashed. Since a horse can finish in multiple slots (first / second or first / second / third), there will be multiple horses who pay to place and show. Because of this, the place and show payoffs will be, in most cases, considerably less than win payoffs will be. Over the course of the past ten years, winners of the Kentucky Derby have paid the following amounts on $2 place bets and $2 show bets: $19.60, $13.00; $13.80, $9.00; $7.40, $5.40; $5.60, $4.20; $5.80, $4.20; $4.80, $3.60; $7.20, $5.80; $6.00, $4.40; $56.60, $24.60 (via disqualification); $6.00, $5.00.

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When we venture away from the win / place / show wagers is when things become interesting. The “exotic” wagers are the wagers that typically pay considerably more than the win / place / show wagers do for two reasons: there are exponentially more combinations that could be winning combinations, and, because of that, the bets are much more difficult to successfully put together. The main exotics for the Kentucky Derby itself boil down to the exacta, trifecta and superfecta wagers (there are multi-race wagers as well as a super hi-five, but those will not be discussed here). How does one go about cashing an exacta, trifecta or superfecta wager? The answer is essentially in the name of the bet.

For an exacta to be successful, a bettor must correctly identify the horses who will finish first and second in the exact order. In last year’s Derby, one would have needed to have Authentic in the “first” slot and Tiz the Law in the “second” slot to cash their exacta, which paid $41.00 for every $2 bet. Two years ago, when 65-1 Country House was elevated to first place and 14-1 Code of Honor was elevated to second place following the disqualification of Maximum Security, the exacta returned $3,009.60 for a $2 wager. If you are not convinced that you are prepared to identify exactly who will finish first and who will finish second, but you like two (or more) horses, then “boxing” is an option. Whenever a wager is “boxed”, it then gives the bettor each of the horses they want to use in every slot of the bet – in this case, each horse they are using in first position as well as in second position. While this may sound like the simplest way to approach any of the exotic wagers, it is not the most efficient and can lead to cost prohibitive bets.

Why does the exacta pay as much as it does? The answer lies within the numbers, as there are 380 potential combinations for an exacta in a 20-horse field. When thinking of a trifecta, think of it as an exacta, but now also add the horse who you believe will finish third in the race. If you correctly identify the horses who will finish 1-2-3 on Saturday afternoon and play a trifecta, you will likely be a happy camper for the rest of the day. In last year’s Derby, 46-1 Mr. Big News finished third behind Authentic and Tiz the Law, producing a trifecta that paid $1,311.80 for a $1 bet. In the 2019 Kentucky Derby, the trifecta was comprised of horses whose odds were 65-1, 14-1 and 5-1 and paid $11,475.30 for a $1 bet. Simply adding the third-place finisher to the equation may not sound like it is that difficult but consider this: in a 20-horse field there are 380 potential exacta combinations, whereas there are 6,840 potential trifecta combos.

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Last but certainly not least is the superfecta, which, on Kentucky Derby day, reigns supreme. This is the wager that is far and away the most difficult to hit but is also the most enticing, as it often produces life-changing payouts. To illustrate the level of difficulty in hitting the superfecta (correctly identifying the horses who finish 1-2-3-4 in exact order) in the Kentucky Derby, refer to the trifecta. In a 20-horse field, there are 6,840 unique combinations for the trifecta (1-2-3 in exact order). Compare that number to the 116,280 unique combinations possible in the superfecta, and it becomes easy to understand why the wager pays as much as it does year in and year out. The superfecta in the Kentucky Derby routinely pays more than $20,000 on a $1 wager, drawing the attention of the serious horseplayer year in and year out. On occasion, the wager can pay north of $100,000 or more, with the largest superfecta payout in history coming in the 2005 Derby. In 2005, Giacomo shocked the world, winning the Kentucky Derby at odds of 50-1. Finishing behind Giacomo was (in order) 71-1 Closing Argument, 9/2 Afleet Alex and 29-1 Don’t Get Mad, resulting in a superfecta that paid $864,253.50 on a $1 bet.

When approaching this year’s Kentucky Derby, the best thing anyone can do is be realistic about their level of knowledge and understanding of horse racing. If you are someone who only bets one horse race a year, do not be afraid to play a horse to win / place / show and potentially collect a few bucks when all is said and done. If you are someone who has some knowledge and slightly deeper pockets, wading into the exacta pool and even the trifecta pool is not an outrageous approach, recognizing that these wagers are much more difficult to successfully navigate. The superfecta is likely to be too expensive for many people enjoying Saturday’s race, but, for some, it represents the Holy Grail of wagering in horse racing. Whichever bets you decide to partake in, do so responsibly and enjoy the 147th Kentucky Derby.