Inside the Kentucky Derby

The "Run for the Roses" is much more than a two-minute horse race.

Inside the Kentucky Derby

The Kentucky Derby is the jewel of horse racing, but "The Run for the Roses" is much more than a two-minute horse race.

The Derby has almost 150 years of history, tradition and stories. And for the lucky few who cross the finish line first, life changes for everyone involved: the horse, jockey, trainer and stable.

But how did a win at Churchill Downs on the first Saturday of every May become the most prestigious honor in horse racing?

From how horses qualify to the hats to gonzo journalism, here's everything you need know about the Kentucky Derby.

How Was the Race Born?

The Kentucky Derby was first run on May 17, 1875, at 1 1/2 miles. It was shortened to 1 1/4 miles the following year, and that’s where it stands today.

In front of an estimated 10,000 fans, 15 3-year-old thoroughbreds competed, and jockey Oliver Lewis guided a colt named Aristides to the first victory in Kentucky Derby history.

Future Hall of Famer Ansel Williamson was the trainer.

How Do Horses Qualify?

Mike Smith rides Justify to victory during the 144th running of the Kentucky Derby in 2018.

Called "The Road to the Kentucky Derby," horses qualify under a points system. It covers many stakes races for 2- and 3-year old thoroughbreds.

There are 20 spots available for the race itself with four additional spots designated as "also eligible," meaning if a starting horse is scratched, the horse with the next highest point title is inserted in the race.

Two of the spots eligible go to the top points getter from the Japan Road and Europe Road, and the remaining spots go to the top U.S. horses, although the Japanese and European offers could be declined.

What Is the Greatest Performance?

Hands down, this goes to perhaps the greatest thoroughbred of all time, Secretariat.

With Ron Turcotte in the saddle, the 1973 Kentucky Derby is where Secretariat began his amazing run for the Triple Crown. He showed his complete dominance as he weaved through the field on the backstretch and took ownership on the final turn. He covered the 1 1/4 miles in a record time of 1:59.40 — which was the slowest of his three Triple Crown performances.

The irony of this race was that Sham’s time would’ve broken the Kentucky Derby record, but he had to settle for second place behind a legend.

What Is the Greatest Race?

The Fighting Finish — Brokers Tip, ridden by Don Meade, right, and Head Play, ridden by Herb Fisher, during the fighting finish at the 1933 Kentucky Derby.

This was a tough one to pick, but on May 6, 1933, Kentucky Derby race fans witnessed something they had never seen or will ever see in a major race.

Brokers Tip, ridden by Don Meade, and Head Play, ridden by Herb Fisher, had an epic battle down the stretch as the two jockeys began to grab each and, yes, whip each other instead of their horses. The two still were whipping each other as they crossed the finish line.

Brokers Tip was declared the winner of the race, and the two jockeys continued their fight in the jockeys' quarters. They were suspended for 30 days.

Who Are the Greatest Trainers?

Whirlaway, wearing the rose blanket after winning the 1941 Kentucky Derby, with trainer Ben Jones.

Ben A. Jones is the only trainer to bring home six Kentucky Derby winners. His winners included Lawrin (1938), Whirlaway (1941), Pensive (1944), Citation (1948), Ponder (1949) and Hill Gail (1952).

Under Jones, Calumet Farm in Lexington, Kentucky, became one of the greatest stables of all time. All but one of Jones’ Derby winners came from Calumet.

Three trainers have four victories each and should be mentioned: Bob Baffert, D. Wayne Lukas, and Henry J. Thompson.

Which Jockeys Have the Most Victories?

Jockeys Bill Hartack and Eddie Arcaro have the most Kentucky Derby victories with five each.

Hartack won with Iron Liege (1957), Venetian Way (1960), Decidedly (1962), Northern Dancer (1964), and Majestic Prince (1969).

Arcaro won with Lawrin (1938), Whirlaway (1941), Hoop Jr. (1945), Citation (1948) and Hill Gail (1952). Whirlaway and Citation both went on to win Triple Crowns.

Of note, Bill Shoemaker should have won five Kentucky Derby races, not Hartack. In 1957, riding Gallant Man, Shoemaker misjudged the finish line, and he stood up too soon, and Hartack steered Iron Liege past Shoemaker for victory.

How Many Women Jockeys Have Competed?

Jockey Rosie Napravnik rides Mylute during the 139th running of the Kentucky Derby in 2013.

A total of six women have competed in the Kentucky Derby.

Diane Crump broke the barrier in 1970 and was the first female jockey in Derby history.

Since Crump, the other women riders were Patti Cooksey, Andrea Seefeldt, Julie Krone, Rosemary Homeister Jr. and Rosie Napravnik.

Napravnik has the highest finish among women with a fifth place showing in the 2013 Kentucky Derby.

Of note, a lawsuit was filed in the late 1960s that allowed women to become licensed jockeys.

Who Were the Biggest Longshot Winners?

Calvin Borel riding Mine That Bird won the 135th Kentucky Derby in 2009.

In the 1913 Kentucky Derby, Donerail went as a 91-1 betting underdog. At the top of the stretch, Ten Point was leading the pack, but Donerail turned it into a fight and stunned the crowd as he pulled away for victory.

The payoff for a $2 wager was $184.90, and his time of 2:04.8 was the track record.

Some other longshots who won the Kentucky Derby were Mine That Bird in 2009 (50-1, $103.20 payoff), Giacomo in 2005 (50-1, $102.60) and Gallahadion in 1940 (35-1, $72.40).

How Many Fillies Have Won?

A total of 40 fillies have competed in the Kentucky Derby, but only three have captured the roses: Winning Colors (1988), Genuine Risk (1980) and Regret (1915).

Of those three, Genuine Risk came the closest to a Triple Crown by finishing second in both the 1980 Preakness Stakes and Belmont Stakes. Winning Colors also competed in the three Triple Crown races, but finished third in the Preakness and sixth in the Belmont, and Regret did not compete.

Six fillies were post-time favorites, including Regret, Nellie Flag (finished fourth in 1935), Prudery (third, 1921), Althea (19th, 1984), Life’s Magic (eighth, 1984) and Serena’s Song (16th, 1995).

What Is the Purse?

Mike Smith celebrates after riding Justify to victory during the 144th running of the Kentucky Derby in 2018.

The purse for the 2019 Kentucky Derby is taking a huge jump from $2 million to $3 million. According to the Courier Journal, the increase stems from investments in historical racing machines.

This increase is the first boost in the purse since 2005, from $1 million to $2 million.

For the 2019 Kentucky Derby, the breakdown of the purses goes this way — $1.86 million for first place, $600,000 for second place, $300,000 for third place, $150,000 for fourth place and $90,000 for fifth place.

How Did Roses Become Part of the Winning Tradition?

Calvin Borel riding Street Sense gets a blanket of roses after winning the 133rd Kentucky Derby in 2007.

In 1883, roses became part of the Derby celebration as all ladies in attendance were presented with roses.

The roses were so popular that Colonel Meriwether Lewis Clark, the builder of Churchill Downs and founder of the Louisville Jockey Club, adopted the rose as the event’s official flower.

Now, they are part of the winning tradition at the Kentucky Derby. A garland of more than 400 roses blankets the Kentucky Derby winning horse, and the winning jockey receives a bouquet of 60 long-stemmed roses.

What's the Story With the Hats?

The Kentucky Derby is not only a special sporting event. It’s also a big dress-up event. The bottom line, however, is all about the hats.

The women wear wide-brimmed, "Southern Belle"-inspired Kentucky Derby hats. They are decorated with flowers, feathers, bows and ribbons of any color to express creativity and individuality.

When women select a dress, it is recommended they keep it simple, to not take away from their hat. Spring wear, with bright colors or floral patterns, is popular.

As far as the men, this is the one day to spread out with a variety of colors, stripes or plaid.

What Are the Favorite Foods Served?

The Derby offers many foods to whet the appetite.

One favorite is the Kentucky burgoo, a spicy meat stew that’s been a Kentucky tradition for more than a century. In fact, the one served at the Derby is made with pork, turkey and beef. And prepare yourself, because it can be quite the hot dish.

Another famous food is the benedictine, a bright green spread that's a mix of cream cheese, cucumber and green food coloring served on white sandwich bread.

Last but no least are cracklins with pimento cheese, or fresh baked pork rinds with a cheese spread, a great appetizer.

There are many other selections, but these are the three best.

How Much Food and Drink Will Be Consumed?

Derby Crowd — Fans crowd the paddock prior to the fifth race at Churchill Downs in 2006.

Bring your appetite. According to Churchill Downs, this is the average breakdown of how much food will be consumed at the Kentucky Derby:

300,000 strawberries
142,000 hot dogs
32,400 jumbo shrimp
30,000 cookies
18,000 barbecue sandwiches
13,800 pounds of beef
11,520 Niman Ranch gourmet sausages
9,700 pounds of chicken
9,000 scallops
8,000 pounds of potatoes
6,480 pounds of Kentucky hydro tomatoes
4,500 pounds of Niman Ranch pork loin chops
1,892 sheets of Derby Pies
560 roasted Niman Ranch turkeys

For drinks, Mint Juleps are the favorite, and 120,000 of them will be consumed at the Derby.

The other most consumed drinks include:

475,000 pounds of shaved ice for mint juleps and oaks lilies
425,000 cans of beer
40,000 oaks lilies (vodka, cranberry juice, triple sec and sweet and sour)
7,800 liters of bourbon
2,250 pounds of locally grown mint

What Are the Specialty Drinks?

The mint julep has been the traditional beverage of Churchill Downs and the Kentucky Derby since 1938. It's been a Southern tradition for more than a century, but people save it for Derby day. Now, it's served with Old Forester bourbon, sugar, water and crushed ice.

While the mint julep is the most traditional drink, other beverages served at the Derby include the Kentucky gambler punch, Basil Hayden’s bourbon thyme julep, a rose for Emily, Cruzan hats off julep, Sunset Boulevard, Woodford Spire, Brown Derby, cucumber julep, and the steeplechase.

We recommend you ask the server what goes into these drinks.

What Are the Betting Options?

Wagering windows — People place bets during the 134th Kentucky Derby at Churchill Downs in 2008.

You can bet many ways at the Kentucky Derby, but here’s the basics.

You can bet on a horse to win, which means the horse has to win for you to win.

You can be on a horse to place, where your horse has to finish in the top two.

Or you can bet on a horse to show, where your horse has to finish in the top three.

The minimum bet is $2.

There’s also exacta betting, where you pick the top two horses in order of finish, or trifecta, where you pick the top three in order.

In the cases of the exacta and trifecta, you can "box" those bets, meaning your top two or top three choices just need to finish in the top two or three, respectively, but the amount of your wager increases.

How Do You Bet?

Betting tickets — A spectator checks her betting tickets after the seventh race before the running of the 139th Kentucky Oaks at Churchill Downs in 2013.

Be prepared when you approach the teller so you’re not fumbling around and the teller may not understand how you’re betting. Also, you don’t want to hold up the line, especially if it’s nearing post time. (Bettors get very nervous if post time is just a few minutes away.)

Make sure you say specifically, for example, "race No. 11, 2 dollars on No. 2 to win," or whatever way you are betting, such as "race No. 11, $2 dollar exacta on No. 2 and No. 5 in that order."

You hand the money to the teller, and a ticket is printed. Before leaving, check the ticket to make sure that’s how you want to bet.

If you’re at a satellite track making a bet, include the track when you talk to the teller, for example, "Churchill Downs, race No. 11, 2 dollars on No. 2 to win."

And good luck.

What Is the Best Way to Bet?

2005 Kentucky Derby — Fans celebrate after placing a winning bet on the seventh race at Churchill Downs in 2005.

This can be tricky. Normally, you would think that the favorite is the sure thing to bet on, but keep in mind that about only a third of the favorites have ever won at the Kentucky Derby.

There is no surefire way to bet. If you can learn how to read the Racing Form, that would be a good start because it gives a detailed resume of each horse from how it performed in previous races to the times it posted, and you can compare that to other horses in the field. A program will not give you that type of information.

If you don’t want to go too deep, have some fun with it. Pick your favorite numbers or names, color of horses or how they are acting, maybe a favorite jockey, and maybe box an exacta bet to increase your chances.

Seriously, the average bettor is not going to make a mint, but if your horse wins, it sure makes for some serious bragging rights.

How Much Money Is Wagered at the Derby and Satellites?

It looks like the amount of money wagered for the Kentucky Derby is on the rise. According to Churchill Downs, wagering from all-sources on the Kentucky Derby Day program in 2018 totaled $225.7 million, an 8 percent increase over the 2017 total and previous record of $209.2 million.

Wagering from all-sources on the Kentucky Derby race increased 8 percent to $149.9 million from the previous record of $139.2 million.

What Is the Greatest Payoff in Kentucky Derby History?

Thomas and Meryl Ritchie — Thomas Ritchie, with his wife, Meryl, holds a copy of their winning $1 dollar Kentucky Derby superfecta ticket and the check they got for one half of the winnings at their home in Kinnelon, N.J., in 2005. Ritchie and his friend, Brian Wien of Allentown, N.J., bet the first four horses in the correct order to win the superfecta and split the $622,262.50, the remainder of the $864,253 after taxes.

In 2005, a person set the all-time record for Kentucky Derby day betting by winning a superfecta bet that paid out a whopping $1.7 million.

Superfecta wagering is when you have to pick the top four horses in exact order, a tall feat to accomplish.

Interestingly, the second-highest payoff in history came in 2018 from an unidentified Austin, Texas, woman, who wagered $18 on a pick five — choosing winners in the four races leading up to the Kentucky Derby and the Derby itself. She came away with $1.2 million.

Where Are the Best Places to Stay?

First and foremost, fans need to book their hotel as early as possible because vacancies fill up fast. Among the best hotels are the Hyatt Regency Louisville or the Brown Hotel. Of course, there are plenty of travel websites to fit your need for location and price.

If you really want to spend some bucks, there’s Hermitage Farm in Goshen, Kentucky, a 700-acre thoroughbred farm that is breathtaking. The house is fully stocked, you have VIP accommodations, and the place can sleep up to 14.

Or check out the Inn at Woodhaven or Bashford Manor. You also might want to check out some vacation rentals around Louisville, or if everything is booked up, you can try neighboring cities like Indianapolis or Cincinnati, which are about two hours away from Louisville, and they are cheaper options, too.

What Are the Best Restaurants?

Welcome to Jack Fry's, an old-school Louisville classic.

Searching through a number of reviews, including Yelp, you can’t really go wrong with most places around Churchill Downs depending on your tests.

The Derby Cafe, for one, is located in the Kentucky Derby Museum and is a solid place for breakfast or lunch, but it’s not open for dinner. It prides itself on hot browns, mint juleps and 50 brands of bourbon, but it also serves fresh pastries, muffins and kolache for breakfast and deli-style sandwiches and the Derby pie for lunch.

For dinner, the betting favorite looks like Jack Fry’s, which features American bistro, Southern-style food, with a live jazz band. The restaurant was established in 1933, and it still has that old-time feel. The dinner menu is loaded with a great variety, such as halibut, ribs, pork chops, lamb chops, Jack’s burger and more.

There are many great restaurants, but these two look like the best bets before and after the Derby.

What Are Some Historical Places to Visit?

The obvious place to visit right out of the gate is the Kentucky Derby Museum, where the history of the greatest horse race is laid out in exhibits and historical artifacts, but you will need to reserve early to book a tour.

Other historical places include the Louisville Slugger Museum and Factory, the Louisville Slugger Walk of Fame along Main Street, Museum Row on Main Street that includes Frazier International History Museum, Kentucky Science Center, Kentucky Museum of Art and Craft, Muhammad Ali Center, Kentucky Center for the Arts, Evan Williams Bourbon Experience, and Kentucky Peerless Distilling Co.

What Are the Best Attractions?

There are definitely plenty of places to have fun around Louisville leading up to and past the Kentucky Derby.

If you want a little adventure, check out the Louisville Mega Caverns, especially the Mega Zips that cover around 17 miles of underground passageways and feature six zip lines and two challenge bridges.

Or how about an amusement park, where you can find some awesome rides at the Kentucky Kingdom, including six roller-coasters.

If you want something a little more tame, try the Louisville Zoo or Waterfront Park for some great views.

Gonzo Journalism

Ralph Steadman illustration — Ralph Steadman's illustration that accompanied Hunter S. Thompson's famous story on the Kentucky Derby.

The Kentucky Derby was the birth of gonzo journalism in 1970 ,thanks to a sort-of-sports article written by Hunter S. Thompson, who took on the style during the 1970s.

Gonzo journalism was more of a first-person account of a story that lacked objectivity.

Thompson wrote "The Kentucky Derby Is Decadent and Depraved" on the 1970 Derby for Scanlan's, but the real motivation for the piece was Thompson had no real story as his deadline approached.

Thompson had a bad vantage point of the race, so he focused more on the race’s celebration and depravity that surrounded the event. The rest is history.