The biggest historical upsets at the Kentucky Derby of all-time came in 1913 when Donerail won as a +9100 underdog. When the horses take their gates at the 147th Run for the Roses this Saturday (May 1st), it’s unlikely that any of them will be listed much longer than +5000. But when it comes to betting, there could still be big payouts if the favorites falter. And there is a modicum of precedence for just that in the recent history of the race.

In 2019, Country House won as a +6500 longshot in arguably the most controversial Derby ever. 

A decade earlier, Mine That Bird was full value for the win as a +5000 underdog, blowing away the field by 6-and-3/4 lengths despite sitting dead last for the first 75% of the race. In the image below, you can see Mine That Bird about eight lengths back of the entire field on the back stretch.  

Just four years before Mine That Bird’s epic comeback, Giacomo also won as a +5000 underdog, barely edging out Closing Argument (a +7100 longshot, himself) by half a length. 

Last Saturday, Derby pundits were keying in on two relative longshots who have a real chance to surprise. They aren’t nearly as long as Donerail, Mine That Bird, or Giacomo, but their odds were long enough to grab some attention. 

King Fury (+2000) was described as an unseasoned horse with a huge upside, and upside is what bettors should be looking for in a viable longshot. King Fury had been on a long hiatus before coming back with a vengeance at the Stonestreet Lexington Stakes. 

If he had another race or two like that under his belt (career-best 95 Beyer Speed Figure), he’d be among the favorites, especially considering the stamina he showed in Lexington. Bettors aren’t willing to give him the benefit of the doubt just yet, though. 

Another longshot that got some attention was Soup and Sandwich (+3000). A daughter of the legendary Tapit, Soup and Sandwich is a frontrunner that dominated her first two races and then nearly held on against a great field at the Florida Derby, ultimately finishing second to Known Agenda, a top-three favorite last Saturday. If the pace is right in the first three-quarters of the race, she could have enough to hold the lead she’s likely to have.