When it comes to the Kentucky Derby, chalk bettors have had it easy. Those horse racing handicappers who love to back the favorite to win the Run for Roses have cashed ticket after ticket.
The favorite won the Kentucky Derby five straight times from 2013 through 2018. Orb won the roses in 2013, followed by California Chrome, eventual Triple Crown winner American Pharoah, Nyquist, Always Dreaming, and, like his stablemate, TC winner Justify in 2018.
If the stewards hadn’t disqualified Maximum Security in 2019, he too would have won the Kentucky Derby as the bettors’ choice. Authentic upset favored Tiz the Law in the 2020 running.
But Authentic’s victory came in the coronavirus-affected year. If we put an asterisk next to Country House in 2019 and Authentic in 2020, we realize favorites have dominated America’s most famous horse race.
Before 2013, though, favorites struggled to get it done. Derby history is littered with chalk equines who couldn’t get their picture taken on the first Saturday in May.
5 Most Disappointing Derby Favorites
1. Native Dancer – 1953
Heading into the 1953 Kentucky Derby, Native Dancer had built an 11-0 record. He had dominated his competition in the Hopeful, the Grade 1 Futurity, the Wood Memorial, and the Gotham.
Most expected Native Dancer to not just win the Kentucky Derby. They thought he was a Triple Crown horse.
But Native Dancer failed in the Run for the Roses, losing to longshot Dark Star. He’d go on to win the rest of his races, including the Preakness and Belmont, and end his career with a 21-1 record.
2. Point Given – 2001
Bob Baffert won the Kentucky Derby in 1997 with Silver Charm and 1998 with Real Quiet. Baffert believed that Point Given was better than both his previous Derby winners.
The Santa Anita-based trainer says instead of giving Point Given three preps, he provided him two, and that’s why the big horse with a red hue to his coat failed to run his best in the Kentucky Derby.
Florida Derby winner Monarchos ran past Point Given, who finished fifth. Point Given would end his career winning four Grade 1 races in a row, the Preakness, Belmont, Haskell, and Travers.
3. Holy Bull – 1994
Warren Croll Jr. trainedHoly Bull wasn’t bred to be a champion. Sired by Great Above and from an Al Hattab sired broodmare, Sharon Brown, most didn’t expect the greyish colt to be the best three-year-old in 1994.
Holy Bull had won the Grade 1 Futurity as a two-year-old. He won 3-of-4 before the Derby try, the Grade 2 Hutcheson, Grade 1 Florida Derby, and Grade 2 Blue Grass Stakes.
Because he had won two of the four most essential preps, the Florida Derby and the Blue Grass, handicappers made Holy Bull the chalk to win the first jewel in the Triple Crown.
Leading up to the race, though, many said Bull didn’t have the breeding to run in the slop. So when the Churchill Downs racetrack came up muddy, Holy Bull failed to make an impact, finishing twelfth.
Nick Zito trained Go for Gin won. Go for Gin wouldn’t win again. He finished second to Tabasco Cat in both the Preakness and the Belmont.
Holy Bull won six straight to grab horse of the year honors. Four of the six wins were grade 1 events, the Metropolitan, the Haskell, the Travers, and the Woodward.
4. Empire Maker – 2003
The great Bobby Frankel had never won the Kentucky Derby. Frankel had his best shot ever when he put the saddle on Empire Maker.
After the 2003 Wood Memorial, Empire Maker’s Derby victory was a close to sure thing. The Juddmonte Farm owned, Unbridled sired colt had gotten past rival Funny Cide in the Wood Memorial.
Funny Cide turned the tables on Empire Maker in the Derby, holding off his foe to become the first gelding to win the Derby since Clyde Van Dusen in 1929.
Empire Maker had a bruised heel heading into the race. Although many believe that’s why Frankel’s runner failed to catch Funny Cide, the truth may be simpler.
The chalk had yet to develop into a dominant racehorse. Five weeks later, in the Belmont Stakes, Empire Maker put on a show, dusting Funny Cide by7 to 8 lengths.
5. Arazi – 1992
In hindsight, Arazi should not have gone off the favorite to win the 1991 Kentucky Derby. He had impressed so much winning the 1991 Breeders’ Cup Juvenile that many believed he was a super horse.
Arazi had not developed from his two-year-old season. Not only that, but the equine based in France had prepped in a single turf race before the Derby.
So when Lil E. Tee won the Run for the Roses and Arazi finished eighth, it shouldn’t have surprised anyone. But it did because bettors had wagered Arazi down to 4-to-5 odds.
Undefeated 2020 Breeders’ Cup Juvenile WinnerEssential Quality will go off the favorite to take the roses on May 1. The Brad Cox trained runner and Godolphin owned horse sired by Tapit has the tools to win the Derby.
Will he get it done? Individual racebook operators that provide free betting software through individual-run sportsbooks have noticed an increase in future Derby bets flowing to John Sadler trained Rock Your World.
Essential Quality must get past the Candy Ride sired monster in the 2021 Kentucky Derby. If he doesn’t, he may bump one of the failed five from the current list.