A Girl's Guide to Gambling. How to Bet on the Kentucky Derby.

Gambling on horse racing is as American as apple pie.  Like anything else, there are terms to learn and rules to understand, but none of it is very complicated.  At first glance it might sound daunting, but I can assure you that anyone (literally, anyone, 18 and older) can bet on ponies.

When the horses charge through the gates on Saturday, make sure your bets have been placed and appreciate your new skill - a gambler! 


Horses Racing


There are two main rules of thought on gambling. Straight and Exotic.  

Straight wages allow you to bet on one horse.

  • WIN– You’re betting that your horse will come in first place. If your horse finishes in first, you collect.
  • PLACE– When you bet on your horse to “place,” you’re betting that he will come in first OR second. If your horse finishes in first or second, you get to collect. Payout for a place bet is less than a win wager, but you do have the security of being able to cash in if your horse finishes in the top two spots.
  • SHOW– You’re betting that your horse will come in first, second, OR third. Since you’re hedging your bets, you have a higher chance of winning, but the payout for a show bet is substantially less than a win or place wager.
  • ACROSS THE BOARD– When you bet across the board, you’re betting your horse to win, place, AND show. An across-the-board bet is what’s called a “combo straight wager” because it’s three different bets (win, place, AND show) in one. Across-the-board bets aren’t usually a good wager because they’re expensive and have less profit potential.
  • WIN/PLACE, PLACE/SHOW– Similar to an across-the-board bet in that you’re making multiple straight wagers in a single bet. In a win/place bet, you’re betting your horse to win AND place. If he wins, you collect both the win and place money. If he finishes second, you collect just the place money. 

Girl Looking at Bets

Exotic Bets allow you to bet on multiple horses in a single bet, which increases your profit potential. But, these are much harder to get right.

  • EXACTA– You’re betting on two horses to come in first and second in an exact order. For example, if you placed a $2 exacta on horses 3 and 5, you can only collect if horse #3 comes in first and horse #5 comes in second. You can also “box” your exacta bet which means your two horses can come in any order in the top two spots and you still win. 
  • TRIFECTA– You bet that three horses will finish in first, second, and third in an exact order.  
  • SUPERFECTA– You bet that four horses will finish, first, second, third, and fourth in an exact order. As with exactas and trifectas, you can box a superfecta at an additional cost. The minimum bet is often 10-cents, which makes it more appealing to many people.

Now for some horse betting strategy!  

The Kentucky Derby is an amazing race where anything can happen, from the favorite leading the pack all the way home, to hunch bet or long shot kicking it in gear up the back stretch and knocking our socks off!  The horse that wins this race will go on to enter the second, and hopefully the third, in series of races called the Triple Crown, which include the Kentucky Derby, The Preakness, and the Belmont.  Each of the races are held on a Saturday, two weeks a part from each other, starting with the derby, which is always the first Saturday in May.  The races also vary in length.  The Kentucky Derby is a mile and 1/4, the Preakness is slightly shorter at a mile and 3/16th and the Belmont Stakes is the longest of the three at a mile and 1/2.  The last horse to win the Triple Crown was American Pharoah in 2015.  Before then a horse had not ran and won all three races since Affirmed in 1978.  

The Sheets

Now there is a lot of strategy to horse racing, and a lot of handicappers will spend weeks doing the numbers, or what some refer to as "the sheets" which is a really detailed worksheet in which you analyze each horse, their past performances, their rate of improvement, and the track conditions under which they've performed.  They look forward at the weather reports for upcoming track conditions and even the past average speed time for the course itself.  Handicappers will even factor in numbers like wind direction and air/speed velocity.  If you are really interested in making a mathematical analysis and bet, you can go to www.thesheets.com and get the worksheets as well as all current racing data for both the horses and tracks there.  It's a lot of work and quite frankly, not as much fun as making, say, a hunch bet, or cheering on your favorite jockey or trainer.


Some people who follow racing are familiar with the most famous jockeys, trainers and stables that own the horses.  Jockeys who have won the Kentucky Derby before, like Victor Espinoza who has won it twice, and Calvin Borel, who has won the race 3 times, are crowd favorites.  Bob Baffert and Todd Pletcher are two top trainers that almost always have a horse, or several horses running in the derby each year.  While betting on one of these veterans doesn't guarantee a win, it may increase the odds having extensive experience with the race and racetrack. 

Hunch Bet  

My favorite way to bet on the Kentucky Derby is most definitely a "hunch bet".  A hunch bet is really just when you look at the list of horses, and fine the one name that calls out to you or that you can relate to and you go with it.  It's much more fun than doing math, and if you'll win you'll always remember.  Racehorses always have fun and crazy names so go down the list and see what speaks to you!  

Most people are going to bet on the calculated track favorites, and majority of the time they will win/place/show, however, when you put 20 horses and 20 riders in the most exciting race of the year, anything can and will happen.  My handicapper friends talk odds all day long, and myself, having grown up around racehorses my entire life, I always tell them, horses are spirited, unpredictable animals with good days and bad... if there are 20 horses in that field, as far as I am concerned, each horse has a 20/1 chance of winning that race, despite the math!  I felt more confident of that statement when in 2005 a 50-1 long shot came in to win the derby named Giacomo.  The only reason I bet on that horse was because I had met a man named Giacomo the day before!  It was a complete hunch!   In 2012 I saw a horse on the field named "I'll Have Another."  As a bartender in my younger days, I related to this as a bar tending reference meaning, "I'll have another drink."  He wasn't the favorite to win, but he did!  In 2014, I actually owned an off-track racehorse, so I looked down her lineage and the lineage of the horses running that year and found a horse named Commanding Curve who was a direct nephew of my horse.  I had to cheer for family!  While the horse did not win the race, I had exacta and trifecta boxed him in over the favorite and ended up having a really great day at the track!  

The way others choose their winners, some simply pick their favorite numbers or dates without looking at the field. Other people even choose horses just based on the colors they like.   The grey thoroughbreds are the easiest horse to spot in the pack during the race making them a favorite of many derby day gamblers.  I'm personally partial to the big reds (chestnuts) like the great Secretariat.  

Always bet on a long shot

You definitely don't have to do this, but if you win, you'll be thrilled you did!  Long shots are the horses with the worst odds, and deemed by the track as the horses least likely to win the race.  They usually have odds of anywhere between 30-1 all the way up to 50-1.   So why would you bet on a long shot to win?  Because if they do, the pay out is much much higher than it would be if you were betting the field on a favorite that goes off at 5/2.  So every day I'm at the track, I'll put a bet on a long shot to win.  After all, it is gambling right?  

Making your bet interesting because, long shots are more fun!

While yes, there is a really good chance the "favorite" horse will win the race, and you do want to bet on the horse that is going to win, it's not as much fun.   From a gambling perspective, the more likely your horse is to win the race (the better his odds) the less his payout will be if he does win.  Which at times, almost makes it not really worth it to make the $1-5 dollar bets on all of the favorites.  You won't make any money, or you'll only make a few dollars here or there, especially if you are betting the horse to win, place or show.  There is just no payout.  So to make your bet fun and interesting, instead of betting $10 on the favorite horse you want to win and only earning $5, you can make 10 $1 Trifecta bets, or 5 $2 exacta bets by pairing your favorite to win, with a long shot or two!  The reason this makes it interesting is if the favorite comes in first, second or third, (and in a large percentage of the time the favorite either wins, places or shows) and you have him boxed with a long shot that wins, places or shows, you're going to have a nice pay day!  Depending on the odds of the horses w/p/s along side the favorite, that $2 exact or trifecta can win you a few hundred dollars or more.  If your bet consists of only long shots and they win, you will get to take a really nice vacation.   

The year that the long shot Giacomo (the 50-1 long shot) won the race in 2005, a $2 exacta bet payed out $8,814.80, and a $2 Trifecta bet paid out $133,134.80!  If you were lucky to have picked all four horses in the superfecta, you were winning $864,254.20 on a $1 bet!  Does this happen often?  Definitely not, racetracks aren't operated on winners... but it does happen in different degrees, like winning the lottery. So don't be afraid to place your hunch bets and cheer your favorites.  Whether you're working the sheets or choosing your favorite name, just remember to be responsible with your bets and keep them modest!  With a long shot and a little luck a $1-2 bet can go a long way!   Have fun and best of luck!  


Fashion at the races KY Derby

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