Biggest Upsets Ever to Win the Kentucky Derby

Biggest Upsets Ever to Win the Kentucky Derby

26 April, 2023

The Kentucky Derby is right around the corner. That means spring has sprung and summer is right around the corner. This year’s Derby is on May 6, 2023.

Seeing a long chance racing horse win the Kentucky Derby is one of the most exciting moments in all of sports. One of the greatest surprises in Derby history was pulled off by Rich Strike only last year, who was 80-1 at the start. Rich Strike narrowed the deficit and finished just a hair ahead of the competition as it seemed like the entire nation watched with bated breath. The biggest upset in Kentucky Derby history, however, was not Rich Strike.

The top five long shots to ever win the Kentucky Derby are highlighted below.

5. Giacomo, 50-1 (2005)
Giacomo, who was ridden by Hall of Fame jockey Mike E. Smith, started in 17th position and quickly closed a significant distance in a half-mile time of :45.2. In the race, Smith won the Derby for the first time. Giacomo would lose races at the Preakness (third) and Belmont (seventh), like many Derby longshot winners. But his triumph in 2005, which was at the time the second-largest upset ever, is remembered as one of the classic performances.

4. Mine That Bird, 50-1 (2009)
Mine That Bird improved from a far last to a distant first on a muddy track, winning by over 16 lengths. The margin of victory in that triumph was the greatest at the Kentucky Derby in more than 60 years, and it tied for the second-longest upset in history at the time. He surprised the horse racing community by riding the fence from last to first coming off the second bend.

3. Country House, 65-1 (2019)
The Derby course in 2019 was among the most challenging in recent memory. He left Gate 20 and quickly positioned himself behind the majority of the group. The first horse to cross the finish line, Maximum Security, was later disqualified for swerving into two other horses. Although jockey Luis Saez was able to straighten him up, Maximum Security was ruled to have been disqualified. Despite the contentious outcome, bettors on Country House received their winnings.

2. Rich Strike, 80-1 (2022) 
On Friday, May 6, 2022, at 8:00 a.m., Rich Strike was not a participant in the Kentucky Derby. On Saturday, May 7, he had won it by 7:00 p.m. Rich Strike, who finished with unbelievable odds of 80-1, entered the race as a last-minute scratch. In addition to defeating one of the strongest Derby fields in recent memory, Rich Strike’s rider Sonny Leon skillfully threaded him through the pack rather of taking an inside or outside channel. He finished with one of the quickest final stretches ever and won by a hair.

1. Donerail at 91-1 (1913)
Donerail’s upset is still unmatched and could continue to be so even after a number of long odds failed to win the Kentucky Derby in the 2000s. Coincidentally, Churchill Downs had recently finished a major renovation in time for the 1913 season, during which time betting limits had been reduced to $2. Due to the “overcrowded” nature of the field this year, Donerail was housed three miles from the track. Donerail walked to the racetrack since it was 1913. He established a track record for the day’s final event of 2:04.8.