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Horse racing takes place nearly every day of the year. However, the Kentucky Derby (also known as the Run of the Roses) doubtless draws the most attention, fanfare, and betting volume of any other event on the horse racing calendar.

The Kentucky Derby is run on the first Saturday in May at Churchill Downs in Louisville, KY. It might be the biggest horse racing event of the year, but what makes the Derby different than all other races, and how should you bet on it?

In this guide you’ll learn:

  • Why the Kentucky Derby is such a big deal
  • Several strategies to successfully handicap the Kentucky Derby
  • Ways to wager on the Run for the Roses

The Kentucky Derby Explained

While Churchill Downs is a historic venue for horse racing on the vast majority of race days it is mostly empty. Everything changes on Kentucky Derby day, as over 100,000 people flock to the track to take in the highest profile race of the year.

Let’s delve into what makes this race bigger than all others.

A Brief History of the Kentucky Derby

The Kentucky Derby has been run since 1875.

A laundry list of the greatest horses of all time have won the Kentucky Derby. Secretariat, the fastest thoroughbred in history, prospered in a record time 1973. The previous mark was held by champion Northern Dancer in 1964. War Admiral, Whirlaway, Citation, Seattle Slew, Affirmed, and American Pharoah all were first across the finish line in Louisville.

The combination of longstanding traditions and a history of elite participants provides the Kentucky Derby with its prestigious reputation.

The Kentucky Derby Is a Component of the Triple Crown

One of the most difficult things to accomplish in all sports is winning the Triple Crown. As such, it’s no wonder that the Triple Crown generates such attention with the horse racing community. Winning the Triple Crown requires a three-year-old horse to win all three races, which are all races at different distances at separate times over a five-week span.

The Kentucky Derby is the first of three racing legs of the Triple Crown’s series. Two weeks later the Preakness Stakes takes place in Baltimore, followed by the Belmont Stakes in New York.

More Horses Participate Than Normal

Most horse races have somewhere between 5 and 10 runners. The Kentucky Derby is significantly larger, welcoming an elite crop of 20 entrants.

A series of prep races that help determine who the fastest three-year-old horse is in the lead up to May ensures that all of the top contenders get a spot in the Kentucky Derby.

In the days leading up the Kentucky Derby, the great jockeys and trainers throughout the country descend upon Louisville to prepare to compete against each other on Derby Day.

The Kentucky Derby Is Chaotic

Like all sports, horse racing involves a significant degree of luck. The more obstacles present during a race, the more likely for something unusual to happen in a race.

If you have 20 horses racing, it’s almost inevitable that someone is going to get bumped or jostled. While you see this from time to time in horse racing, it is a near certainty in the Kentucky Derby. It’s yet another element that makes the race consistently unpredictable.

With more horses on the track, it’s likely that some horses will get stuck behind a wall of equine (created by the sheer volume of horses on the track) and have no room to get around after the race’s initial stages. Other horses will be forced to run wider than normal because not every entrant gets to sit right along the rail and save ground on the turns. With such a high density of horses racing, it often creates traffic problems.

If racing wasn’t a big enough problem, the weather is notoriously up in the air on Derby Day. This means that the track conditions can change in a hurry. If it pours rain, you can expect the dirt surface to turn to mud, drastically altering the complexion of the race.

Even if a horse is the best in the world racing on a certain surface, that doesn’t necessarily imply that they’ll be able to translate that to such radically different conditions. Sometimes a big longshot loves the mud.

What to Expect From the Overall Environment

Horses feel pressure and so do their human connections (jockey, trainer, owner). Different people and horses react to stress in varying ways, and the Kentucky Derby is definitely one of the most stressful events on the racing calendar.

When tension is high people often make mistakes. A trainer could work his horse too hard or not hard enough leading up to the big race. A jockey could make a move too early or wait until it is too late to get his horse moving at its fastest down the stretch. Whether it be an error riding or training, mistakes tend to happen when tension is high.

Some horses suffer from the long walk to the starting gate, waiting for 19 competitors to get situated, and the defining noise of a massive crowd. Others thrive under those conditions.

Betting the Kentucky Derby

With many options comes great opportunity. It is difficult to parse 20 horses and predict who will bow to pressure. Betting the Derby is no doubt a challenge, but it’s a lucrative one if you’re successful.

In addition to normal handicapping strategies such as closely examining each horse’s most recent races, and trying to determine how the race will be run (who will be ahead early, who will look to rally from behind), there are several strategies unique to the Kentucky Derby that are worth knowing and considering before betting.

Consider the Pace of the Races

The pace of any race is important. If the early leader is able to go slowly and exert little effort, he has a pretty good chance to save his energy and have enough kick left late to go wire-to-wire. Conversely, if there is a speed battle in the early going, the front runners are likely to get tired. As such, this sets up horses who have something left in the tank down the stretch.

Because the Kentucky Derby has 20 horses, it is very rare for a horse to get loose on the lead.

There are always horses amped up and aggressive early who end up falling out of position. However, taking it really easy early on and having to pass 17 or 18 or 19 horses is challenging. It is really difficult to find racing room and avoid going too wide if you are too far behind.

The horses that win the Kentucky Derby are very often those sitting in a good position just off the pacesetters. When handicapping, you are looking for tactical speed, enough to keep up and be in a good spot, but not blazing front running early speed that is hard to harness.

Stamina Matters

The Kentucky Derby is a 1.25-mile race. That is the longest race that most, if not all of the contenders have ever been in.

Assessing which horses prefer distance races to sprints is important. This can be done by looking at how they have done in previous changes in distance, and by checking out their bloodlines. If mom and dad were adept at longer races, that is a good sign that horse has a good chance to fair well in the Kentucky Derby.

What Class Are Horses From?

Some contenders will be more battle tested than others. Consider who horses have raced against previously, and how have they fared.

For example, winning at smaller tracks against lesser competition is not as impressive as beating the best horses at the top venues.

Who Are the Jockeys?

The track record on three-year-old horses is not vast. Some have run as few as two or three races in their life. None have competed in a race as long or with as many entries at the Kentucky Derby,

Meanwhile, the jockeys racing these horses tend to be the same people year in and year out. Considering which humans have been around winners consistently is worthwhile.

Whether it be owners, trainers, or jockeys, they have a much longer resume to examine than the horses themselves.

While trainer Bob Baffert certainly doesn’t win the Kentucky Derby every year, of the two Triple Crown winners in the last generation, he has conditioned both of them. Over the last 10 runnings of the Kentucky Derby three jockeys (Calvin Borel, Victor Espinoza, and Mario Gutierrez) have accounted for six of the victories. Pay attention to these trends.

Recently, Favorites Have Dominated the Derby

In recent years, favorites have dominated the Kentucky Derby. During the past five runnings, the highest priced payout for a $2 win bet was $11.40. However, in the five years previous, each winner paid at least $12.80 and three of the horses that won paid $30 or more.

Alternative straight bets include wagering to place and show. While neither pay as much as a win bet, there is a greater chance to cash these type of gambles. Betting to place means your horse must finish first or second in order for you to cash a ticket. A show wager requires the horse you select to finish first, second, or third in order to win your bet.

Bet to Win!

An informed bettor has the greatest opportunity to be a winning one. Our guides are a great way to learn the in’s and out’s on a wide variety of sports betting topics.

While we can’t pick the winner for you, hopefully, learning the methods of sports betting will point you in the right direction. Betting on sports is great fun and can be profitable if approached in a thoughtful way.

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Dave has been working in sports journalism for over 16 years. He has broadcast, written about, and reported on the NFL, NBA, MLB, the Olympics, horse racing, golf, tennis, and college sports. Dave has created content for the Associate Press, Metro Networks, ESPN, and numerous local publications.