Fun Prop Bets for the 2020 Kentucky Derby

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2020 Kentucky Derby Prop Bets
The first-ever Kentucky Derby happened on May 17, 1875. Approximately 10,000 spectators gathered to watch 15 Thoroughbred horses race a one-and-a-half-mile track.

The Derby has since undergone many transformations including changes to betting methodologies, competition rules, and even the racetrack itself.

Traditionally held in May, The Derby moved to Saturday, September 5th, 2020 in response to the pandemic. “We believe that moving our iconic event to Labor Day Weekend this year will enable our country to have time to contain the spread of coronavirus,” Churchill Downs Inc.

With the Derby fast approaching, I felt inclined to share some fun Kentucky Derby props for 2020 with you. Betting odds are provided courtesy of MyBookie. Wager cut off is September 5, 2020, at 5:30 PM. Get your bets in!

Which Gate Will the Winner Break from?

Gate Payout
1-5 +300
6-10 +170
11-15 +200
16-20 +250

Since 1930, The Derby has used two starting gates. The main starting gate holds 14 stalls while the auxiliary gate holds 6 stalls.

There have been different perspectives on which gate provides the most optimal starting point. For example, some may feel gate 1 is the worst spot to start from because there is more distance to cover before rounding the first bend.

However, others feel gate 1 allows for less bumping and jostling as racers come pummeling out of the gates, allowing said horse to gain its stride much more easily. A majority have agreed gates 14 and 15 are the worst due to the gap between the post that sits between the two gates.

These perspectives may all change this year as The Derby introduces a new gate to Churchill Downs. “We believe that a new custom made, 20 stall starting gate will deliver a clean start for all horses and enhance safety for horses and riders in the Kentucky Derby,” said Mike Ziegler, Executive Director of Racing for Churchill Downs Inc.

This new gate will eliminate the wide gap between gates 14 and 15 that existed with the previous starting gates. With the use of the new gates, this may mean that all positions are equally favored spots to start from.

Let’s take a look at which gates have produced winners. Keep in mind, this is before the introduction of the new gates, which we will see at this year’s race.

Here are some key stats since 2000.

  • 9 horses broke from gates 13 or higher
  • 7 horses broke from gates 15 or higher

Over half of the winners in the last two decades have come from gates higher than 15, except for gate 17. This gate has not produced a top 3 placement since 1988.

Looking at other statistics, we know gate 10 produces about 10% of winners. Still minimal odds.

With the payout at +250, I plan to bet on gates 16-20. The data points to these gates producing the most winners, even though 17 continues to produce goose eggs.

If you would like a safer bet, you can apply the same info above to the following market

Gate Payout
Gate Payout
1-10 +100
11-20 -130

The payouts are less attractive because the bets below require less accuracy. In this case, I would bet gates 11-20 produce the winning horse.

Starting Letter of the Winning Horse’s Name

Letter Payout
A-I +115
J-Z -155

In addition to betting on the winning horse, you can also bet on what letter the winning horse’s name starts with. Let me give you a hint. It is the letter “S.”

Surprisingly, the letter “S” has produced a whopping 19 winners. The letter “B” is the next closest letter with 13 winners.

On the contrary, letters Q, X, and Y have not produced a single winner. While each letter has its own record for winners, simple math tells us to bet J-Z.

The alphabet has 26 letters. Betting A-I only gives you nine shots of hitting the right letter. Even if you removed Q, X, and Y, you would still have at least 13 chances to win.

Bet J-Z.

Number of Words in the Name of Winner

# of words Payout
1 word +700
2 words +600
3 words -155

The names of the horses at The Derby make for a fun time. The names are creative, but the naming process can be quite difficult.

According to, The Jockey club enforces nomenclature rules that include stipulations such as limitations on the number of characters and restrictions on naming horses after famous people.

Horse naming is quite interesting once you dive into it. For betting purposes, I have my money on a horse with two words in its name winning the race this year.

Since 1980, 18 horses with two words in their names have won a Derby title. One and three-word names both came in with eleven total winners each.

There are 15 different horses with two words in their names racing in The Derby this year. In other words, two-thirds of the horses racing have two-word names.

While there may be some favored horses out there with more than two words in their name, the betting return is so much better on two words. With two-thirds of the horses’ names including two words and a +600 return, the risk is worth the reward.

Bet two words.

Age of the Winning Jockey

Age Payout
Over 40.5 years +300
Under 40.5 years -500

At the age of 16, a rider can apply for a jockey’s license. While there is an age minimum, there is not a cap on how old a jockey can be. The age range of working jockeys varies widely between 16 and 58.

Looking at last year’s jockey roster, only a couple of riders are over 40.5 years old. Neither of these jockeys has won a Derby title in ages.

I have not seen an official roster for this upcoming event yet. If we assume the same jockeys will be returning to Churchill Downs this year, I plan to bet the under based on the average ages on the 2019 jockey roster.

If only 2 out of 20 jockeys are over the age of 40.5 years, you are looking at a 10% chance of winning.

Although the return on this bet is not great, if you want to win, bet the under.

Final Thoughts

The Derby is known for its tradition of Thoroughbreds, Mint Juleps and fancy hats. Along with those fun traditions are the quirky bets you can make.

There are plenty of other bets you can place, including which horse will be the prize winner this year. To access those other bets, visit any of the top online betting sites.

The bets which require more precision and accuracy obviously pay a higher return. The bets I discussed give you a little compromise between accuracy and payout.

For best payout, bet these.

  • Winning horse comes from gates 16-20 for +250
  • Winning horse has two words in their name for +200

For some safe bets with a focus on just winning, bet these.

  • Winning horse name starts with “S” for -155
  • Winning jockey is under 40.5 years for -500

You have my thoughts. Grab a Mint Julep and place your wagers!