HomeThe ShuffleKentucky Derby Trivia: Test Your Horse Sense

Kentucky Derby Trivia: Test Your Horse Sense

How well do you know your Kentucky Derby trivia? Hoist a mint julep and prepare to play Derby Jeopardy!

Dating back to 1875, the Kentucky Derby is the longest-running sporting event in the United States. It’s never been canceled, and has been held through two world wars, the Great Depression and the Covid-19 pandemic. It’s the first jewel in the fabled Triple Crown, which also includes the Preakness and the Belmont Stakes.

Take a look at five horses who have a chance to win the Kentucky Derby. Do you want to pick a winner for this weekend’s Kentucky Derby? Statistically speaking, your best bet is a colt whose name starts with the letter “S” and who will break from post position No. 5. Here’s why.

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What’s in a Name

Since 1875, the Derby’s inaugural year, 19 horses with “S” names have won the race. They include Spokane in 1899, Swaps in 1955, Spectacular Bid in 1979, Smarty Jones in 2004, and most recently, Super Saver in 2010. Another “S” horse, Seattle Slew, won the Triple Crown in 1977 and was undefeated in his career.

The most famous name in horseflesh also starts with an “S”: Secretariat, who won the 99th Run for the Roses in 1973 and went on to win the Triple Crown (Secretariat still holds the record for fastest Derby run, completing the course in 1:59:40).

There’s never been a Derby winner whose name began with the letters “Q,” “X” or “Y.” And so far, only three fillies have won the trophy: Regret in 1915, Genuine Risk in 1980, and Winning Colors in 1988.

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Post Position: Winless 17 & the ‘Dreaded Rail’

Historically, the winningest post position has been No. 5 with 10 wins, followed by No. 10 with nine wins.

The only post to never host a Derby winner is No. 17. In 2020, when the favorite Tiz the Law drew post 17, fans were both anxious about the jinx and hopeful to see an old superstition finally disproven. Then the lineup changed. Some horses dropped out of the pandemic race, and Tiz went inside to post No. 14. But Authentic took an early lead, and Tiz the Law finished second.

In the Derby, posts closer to the outside rails (18, 19, and 20) tend to do the worst, and the far inside post—the so-called “dreaded rail”—is also a disadvantage, because it gives horse and jockey no room for error out of the gate. Though eight horses have won from the rail, most were in races that had fewer than 20 contenders. And no horse has won the Derby from the rail since Ferdinand in 1986.

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Test Your Derby Smarts

Statistics, bloodlines, and other minutiae are all part of the race fan’s betting strategy. Before post time this Saturday, let’s see how much you know about the famous Run for the Roses:

Who founded the Kentucky Derby?

Meriweather Lewis Clark Jr., grandson of famous explorer William Clark and namesake of Clark’s partner, Meriweather Lewis. Clark fashioned the race after the Epsom Derby in England. The Derby began as a 1.5-mile race, until 1896, when it was shortened to 1 ¼ mile, or 10 furlongs.

Who won the first Kentucky Derby?

On May 18, 1875, thoroughbred Aristides won the first Derby in a field of 14 horses, under 19-year-old African American jockey Oliver Lewis. Aristides won a purse of $2,830 (about $85,000 today). After the historic win, Lewis hung up his spurs and became a bookie.

How many horses have run in the Kentucky Derby?

Over the past 147 years, there have been 1,957 starters in the Kentucky Derby.

Who was the biggest longshot to win the Kentucky Derby?

In 1913, 91-1 longshot Donerail won against a field of eight horses. A $2 ($58) win bet on Donerail paid out $184.90 (about $5,550 today).

Which jockey has the most Kentucky Derby wins?

Eddie Arcaro and Bill Hartack are tied with five wins each. Arcaro’s winning mounts include Lawrin (1938), Whirlaway (1941), Hoop Jr. (1945), Citation (1948), and Hill Gail (1952). Hartack won with Iron Liege (1957), Venetian Way (1960), Decidedly (1962), Northern Dancer (1964), and Majestic Prince (1969).

Who were the oldest and youngest Kentucky Derby-winning jockeys?

Bill Shoemaker was 54 when he won aboard Ferdinand in 1986. Both Alonzo Clayton (1892 on Azra) and James “Soup” Perkins (1895 on Halma) were just 15 years old when they won. This year, 56-year-old jockey Mike Smith might break the “oldest” record, aboard Taiba. Smith has won 225 Grade 1 races, more than any other North American jockey. He’s won 27 Breeders’ Cup races, more than any rider in history. And he’s won seven Triple Crown races, taking Justify to the Triple Crown in 2018.

Has a woman jockey ever won the Derby?

Not yet. Six women have competed in eight races, starting with Diane Crump in 1970. Although Crump didn’t win at Churchill Downs, she went on to have as many as 235 wins throughout her career.

How old are Kentucky Derby horses?

Three. In North American horse racing, all thoroughbreds turn a year old on January 1, even those born on December 31. So horses get just one shot to win.

How did the Derby become part of the Triple Crown?

In 1919, the thoroughbred Sir Barton became the first horse to win all three races, in just 32 days: the Kentucky Derby at Churchill Downs in Louisville, the Preakness at Pimlico near Baltimore, and the Belmont Stakes at Belmont Park in Elmont, New York. Other owners began sending their horses on the same circuit, simply because they had larger purses. The term “Triple Crown” came into use in 1930 when Gallant Fox became the second horse to win the three races. An American tradition was born.

How did the Kentucky Derby become an international event?

The first network radio broadcast of the Kentucky Derby took place in 1925, with 5 million to 6 million listeners tuning in to hear Flying Ebony win the Derby. By 1932, the race was being broadcast on the BBC radio network. In 1949, the 75th Kentucky Derby was locally telecast for the first time—Ponder won—and went national in 1952. An estimated 10 million to 15 million viewers tuned in to watch Hill Gale enter the winner’s circle. In 1984, the Kentucky Derby was first simulcast at 24 racetracks in the U.S., and a North American record was set for wagering on a single race—more than $18.9 million. The winner that year was Swale (another “S” name!).

Why is the Kentucky Derby called the Run for the Roses?

In 1904, the red rose becomes the official flower of the Kentucky Derby. In 1925, New York sports columnist Bill Corum coined the term “Run for the Roses.” But it wasn’t until 1932, during the depths of the Great Depression, that the 58th winner, Burgoo King, was draped in a garland of red roses. That blanket weighs about 40 pounds, but the Kentucky Derby trophy itself only weighs 3½ lbs.

How much does winner take home in purse money?

$3 million. The winner pockets $1.86 million, or more than 60% of the total purse; the jockey gets 10% of that.

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Here’s to the Horses!

For nearly a century, the Mint Julep has been the traditional beverage of the Kentucky Derby. According to KentuckyDerby.com, almost 120,000 Mint Juleps will be consumed at this weekend’s Kentucky Oaks and the Derby itself. Here’s the classic recipe:

Old Forester Mint Julep

• 2 cups sugar
• 2 cups water
• Sprigs of fresh mint
• Crushed ice
• Old Forester Straight Bourbon Whisky

Make a simple syrup by boiling sugar and water together for five minutes. Cool and place in a covered container with six or eight sprigs of fresh mint, then refrigerate overnight. Make one julep at a time by filling a julep cup with crushed ice, adding one tablespoon mint syrup and two ounces of Old Forester Kentucky Whisky. Garnish with a sprig of fresh mint.

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For more recipes and party tips, visit KentuckyDerby.com.

Watch the Kentucky Derby

Known as “the most exciting two minutes in sports,” the Kentucky Derby generates millions of dollars in bets each year.

In 2020, with no fans in the stands and the race postponed from May to September, the total dropped to just $79.4 million. But it bounced back last year, with fans wagering $233 million on the race.

The 148th Kentucky Derby will take place Saturday, May 7. The festivities start at 2:30 p.m. ET, with a call to post of approximately 6:57 p.m. ET. Watch the race on NBC-TV, at NBCSports.com, and on the NBC Sports App.

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