For nearly the last 150 years, 20 Thoroughbred horses ridden by jockeys barely over 5-feet tall line up in a metal cage before a bell rings and they take off down a dirt track, galloping a mile-and-a-quarter to the finish line, where the winner is met with roses and a million dollar purse.

Now held every first Saturday in May, the Kentucky Derby is often referred to as “the most exciting two minutes in sports” — and for good reason. If you're great at probability, or lucky, you theoretically also have the chance to win some big bucks off a dime.

Let's get into the basics of betting on horse racing!

Basics of Betting

In my younger years, my betting strategy was built on navigating and experimenting with the information provided by previous performance tables in daily racing programs. This includes odds, career starts, trainer and jockey, among other aspects.

The most common and low stakes racing wagers are the

  • Win
  • Win Place Show, one horse that can place anywhere 1st through 3rd
  • Exacta, first two places in order
  • Trifecta, first three places in order

Most bets cost $1 to place and although not easy, it's low stakes and high reward to place a

  • Superfecta, first four places in order, minimum bet of $0.10

On top of this, any bet made in the exact order of finish, can be made a "box," where the order no longer matters. But these bets are often 2-3x as much to place. Larger chance of winning, more you pay, less you earn.

If you're like my dad and enjoy losing and low-risk bets equally, you'll place an insane amount of "10-Cent Superfectas" on each race, trying to guess tens of combinations for the first four places. In all the years we went to the races, I think he's won a Superfecta once or twice.

The best time to play a Superfecta to maximize your profits is when there is a large field to choose from. To give you perspective, in a 12-horse race, there are 11,800 superfecta combinations possible. With a 10-Cent denomination, that is a $1,180 bet. So imagine that once you've mastered the art of probability, how much you could win by placing $1 Superfectas!

The lowest-paying $1 Superfecta to be bet on the Kentucky Derby occurred in 1997 on Silver Charm, a horse with 4/1 odds. Bettors won $350.00 – a considerable prize back then and today. But in the last 20 years, the Superfecta has paid a median prize of $40,000. The three greatest payouts reached $101,285, $557,000, and $864,253 respectively.

As mentioned, this is dependent upon the horse's odds, which are determined by the total money wagered on the horse. When the odds are greater, the horse is considered a "longshot," and the payout rises directly and considerably. Horses with low odds have a higher chance of winning and therefore, pay much less as a reward for predicting their success. The next question is, how do you know who to bet on?

In short: Earnings are dependent on odds, which are determined by the total money wagered on the horse. If everyone is betting on a particular horse, the odds decrease and perceived chances of winning increases,
and everyone wins less $ since the earning pool is split among more of you!

Research Questions

To retrieve this data, I performed a simple HTML webscrape on Wikipedia tables from the Kentucky Derby page.

I manually added each horse's Triple Crown status, the state they were bred in, their odds, starts, wins/places/shows, chances they placed 1st through 3rd in their races, and the superfecta payouts for horses since the late 90s.

These are the variables in the dataset

Based on horse:

  • Triple Crown status
  • State bred in
  • Odds
  • Career starts
  • Career wins, places, shows
  • WPS ratio (wps/starts)

Based on human:

  • Jockey
  • Trainer
  • Owner
  • Jockey's total derby wins
  • Trainer's total derby wins


  • Track condition
  • Time
  • Superfecta payout

Moreover, I aimed to answer these questions:

  • Are the same trainers winning more derbies?
  • Which era has the most Triple Crown winners?
  • Racehorses retire early. Do career starts indicate experience?
  • Is betting on the longshot worth it?

Performance Report of Kentucky Derby Winning Horses by Era

Choose an era to view more information about each horse.

Won at least the Kentucky Derby
Triple Crown winner
Longshot (Odds > 20/1)
Trainer's total derby wins (1 to 6)

Findings Based on Research Questions

Yes, the frequency of dark pink points increases, indicating that trainers seem to be getting better at winning the derby multiple times!

During the second era, between 1925 and 1974, there were two more Triple Crown winners than the most recent era.

More career starts ≠ more experience ≠ more wins. The number of career starts has decreased drastically over the past century from over 100 to 40 at maximum. If anything, the more races a horse runs, the higher the chances of them not always placing 1st-3rd.

And yes, there seems to be more longshot winners than there used to be $$$

How can this chart inform your betting strategy? A few takeaways:

Horses with Triple Crown potential often have (1) lower odds and (2) higher WPS ratios. Horses with high odds
can still win the derby, just usually not all three races.

Even when a horse's WPS ratio is low, look into the trainer's record for previous wins.

Incorporate betting on the long-shot, even just for $0.10.

More racehorse career starts ≠ more experience...they're probably tired!