It’s that time of year again! Grab a mint julep, put on a flamboyant hat (considered to be good luck), and join the millions who will watch the Kentucky Derby on TV this Saturday. In honor of the Derby, I’ve dug up some of my favorite Derby trivia for you to ponder…

Aristides Thoroughbred horse

Aristides, the first winner of the Kentucky Derby

How many horses have won the Triple Crown — the Kentucky Derby, Preakness Stakes, and Belmont Stakes?
A total of 11 horses have won the Triple Crown: Sir Barton (1919), Gallant Fox (1930), Omaha (1935), War Admiral (1937), Whirlaway (1941), Count Fleet (1943), Assault (1946), Citation (1948), Secretariat (1973), Seattle Slew (1977), and Affirmed (1978).

Another interesting bit of trivia is that three of the jockeys of those horses, William Saunders on Omaha, Warren Mehrtens on Assault, and Steve Cauthen on Affirmed, rode the Kentucky Derby only once in their careers — and won!

Assault wasn’t the favorite in any of the three races of the Triple Crown. He was from Texas and there was obvious bias against Texan horses winning the big three races.

Everyone in racing knows Secretariat was the first horse to finish the Derby in under two minutes, but many people mistakenly believe he’s the only horse to do this. The truth is, two other horses finished the Derby in under two minutes, and one of them didn’t even win! Who were they?
Sham ran the Derby in less than two minutes, but finished second to Secretariat in 1973. Monarchos (2001) won the Derby in 2001 in less than two minutes, but didn’t beat Secretariat’s record of 1:59 2⁄5.

Meriwether Lewis Clark, Jr., founder of Churchill Downs and grandson of General William Clark of the Lewis and Clark Expedition.

Who built Churchill Downs and founded the Kentucky Derby?
Meriwether Lewis Clark Jr., grandson of General William Clark of the Lewis & Clark Expedition, built Churchill Downs on property given to him by his cousins, John and Henry Churchill. “Lutie,” as he was called, had a volatile personality and managed to get himself in trouble with his family as a result. Even though he built and managed Churchill Downs and wrote many racing rules that still exist today, he was fired from his position and became a steward at the track. He committed suicide in 1899 after struggling with poverty, isolation from his family, and aging.

What Kentucky Derby winners sired a Kentucky Derby winner?
Twelve horses that won the Kentucky Derby went on to sire a Derby winner: Halma (1895), sire of Alan-A-Dale (1902); Bubbling Over (1926), sire of Burgoo King (1932); Reigh Count (1928), sire of Count Fleet (1943); Gallant Fox (1930), sire of Omaha (1935); Bold Venture (1936), sire of two Derby winners — Assault (1946) and Middleground (1950); Pensive (1944), sire of Ponder (1949); Count Fleet (1943), sire of Count Turf (1951), the third generation to win the Derby in his sireline; Ponder (1949), sire of Needles (1956), also the third generation in his sireline to win the Derby; Determine (1954), sire of Decidedly (1962); Swaps (1955), sire of Chateaugay (1963); Seattle Slew (1977), the only undefeated Triple Crown winner and sire of Swale (1984); and Unbridled (1990), sire of Grindstone (1996).

Regret Thoroughbred horse

Regret, the first filly to win the Kentucky Derby

What fillies have won the Kentucky Derby?
Regret (1915), Genuine Risk (1980), and Winning Colors (1988). Genuine Risk is the only Derby-winning filly to have finished in the money in all three Triple Crown races. has a list of all the fillies that finished the Derby.

Who is currently the oldest living Kentucky Derby winner?
Go For Gin (1994) is the oldest living winner and a resident of Kentucky Horse Park. Sea Hero (1993) was previously the oldest, but he died in July 2019.

See a list of all the winners of the Derby at Wikipedia.