Kentucky Derby Handicapping: Winning Picks and Guaranteed Expert Predictions

Kentucky Derby Handicapping: Winning Picks and Guaranteed Expert Predictions

The Kentucky Derby has been held on the first Saturday in May on 89 occasions and every year except last year, thanks to the Covid-19 pandemic, since 1946. It had been contested on a Saturday for 111 occasions and every day of the week except Sunday. Before 2020, the last time the Derby wasn’t staged on a Saturday was in 1910 and thankfully returns to its normal spot on May 1 this year.

Also before last year, the Derby has been staged outside the month of May only twice: Monday, April 29, 1901, and Saturday, June 9, 1945.

The Kentucky Derby is the oldest continuously held major sporting event in the United States. It has been contested every year at Churchill Downs without interruption since the inaugural running on May 17, 1875 – the first day of racing at the track then known as the Louisville Jockey Club. The Westminster Kennel Club Dog Show, first held on May 8, 1877, is the second oldest.

Kentucky Derby Predictions

In addition to the Derby, the Kentucky Oaks and Clark Handicap have been also been held every year at Churchill Downs without interruption since 1875.

In the time when the Derby was first held and for several decades after, it was common for men and women to wear hats daily, but especially for special occasions and most outdoor events. At Royal Ascot in Berkshire, England, for the Royal Enclosure area, hats are a required element for ladies, so in many ways the Kentucky Derby hat tradition is a reflection and has continued through today.

As the popularity of the race grew, people – especially women — began to wear extravagant hats and fascinators. Men got in on the fun and it’s become a tradition now for many to wear fedoras, bowlers, pork pie, panama and many others to keep up with their dates.

Kentucky Derby Expert Handicapping

Every year Churchill Downs hosts a hat contest (even last year during the  patron-free event, The Kentucky Derby Museum invited people to enter their hats for inclusion in the 2020-2021 “It’s My Derby” fashion exhibit, which was a virtual contest.)

An expert panel of industry insider judges will select 15-20 hats worn by spectators. Three specialty awards will be granted: the “Judges’ Choice Award” for best overall entry, the “Most Representative of Derby Award” for the hat that best captures the essence of the Kentucky Derby, and the “Employees’ Choice Award.”

This year the weather in Louisville on Saturday is expected to be warm and beautiful with highs in the lower 80s, the nice day coming after several days of rain in the area. But a fast track lately for Derby Day has been almost a rarity. Last year the weather was warm and dry with temperatures hovering in the low 80s, but the race was delayed by four months due to the Covid-19 pandemic and held in September, which in Kentucky is a vastly different weather scenario than the first week of May.

However, two years ago Country House (and Maximum Security) won over a track labeled “sloppy” as did Triple Crown winner Justify in 2008. Other runners to have won on a main track labeled sloppy are Orb (2013), Super Saver (2010), Mine That Bird (2009), Smarty Jones (2004), Go For Gin (2004), Citation (1948) and Flying Ebony (1925).

In 2017, Always Dreaming won over a track labeled “wet fast.”

Unbridled in 1990 was the last Derby winner to capture the race over a “good” main track and joined Dust Commander (1970), Carry Back (1961), Venetian Way (1960), Pensive (1944), Omaha (1935), Brokers Tip (1933), Gallant Fox (1930), Plaudit (1898), Joe Cotton (1885) and Buchanan (1884).

Kentucky Derby Expert Picks

Dual classic winner Sunday Silence won the first jewel of the Triple Crown over a “muddy” track, as did Tim Tam (1958), Hoop Jr. (1945), Clyde Van Dusen (1929), Exterminator (1918), Worth (1912) and Riley (1890).

The track condition label of “slow” isn’t used anymore and to prove it, the last time a horse won the Derby over a “slow” surface was Jet Pilot in 1947. Other winners on a “slow” track were Assault (1946), Whiskery (1927), Paul Jones (1920) and Wintergreen (1909).

“Heavy” is also not an often-used track condition, but in 1928 Reigh Count won on a “heavy” main track, as did Stone Street (1908), Pink Star (1907), Agile (1905), Typhoon II (1897), Azra (1892) and Leonatus (1883). One track condition nobody is still alive to remember is a “dusty” track condition and three horses a very long time ago won on a “dusty” track – Ben Brush (1896), Fonso (1880), Day Star (1878).

The beverage of choice and the signature cocktail for both Churchill Downs and the Kentucky Derby since the 1930s is the Mint Julep. Old Forester was introduced in 1870 as America’s First Bottled Bourbon and is currently he manufacturer of the official Churchill Downs mint julep, but also is the founding brand of Brown-Forman Corporation, which now manufactures Early Times Bourbon, formerly the main ingredient for “the Official Mint Julep of the Kentucky Derby” from 1987 through 2014.

Each year, approximately 127,000 mint juleps are served over the two-day period of Kentucky Oaks and Kentucky Derby weekend at Churchill Downs, requiring more than 10,000 bottles of Old Forester Mint Julep mix, 2,250 pounds of freshly harvested mint and 475,000 pounds of ice. The Old Forester Mint Julep is served at Churchill Downs year-round and produced at the Brown-Forman Distillery in nearby Shively, Ky. The highest-priced mint juleps at the Kentucky Derby, which are sold in limited quantity for a whopping $1,000 each, use unique ingredients and bourbon from the Brown-Forman sister brand Woodford Reserve, which is marketed as the “Official Bourbon of the Kentucky Derby.”


Here is the recipe to make your own mint julep:
Simple syrup
· 2 cups sugar · 2 cups water

-Boil together for five minutes, set aside to cool, add a dozen mint sprigs and chill in covered container overnight

· Sprigs of fresh mint

  • Crushed ice
  • Bourbon Whisky


Fill julep cup with crushed ice, adding one tablespoon mint (simple) syrup and two ounces of Bourbon Whisky. Stir rapidly with a spoon to frost the outside of the cup. Garnish with a sprig of fresh mint.

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