The biggest underdog to ever win the Derby was a 91/1 shot
In 1913, the Kentucky Derby had its first big upset when the field’s absolute underdog, a horse called Donerail, bested the entire field and upset a whole lot of people’s exactas. Running at an astronomical 91/1, the horse asserted itself in the final sixteenth-mile for a win over favorite Ten Point. The $2 win payoff of $184.90 is a Derby record to this day. Ridden by Louisville’s own impeccably named Roscoe Goose, Donerail kept it slow and steady until the home stretch, when his relatively green legs carried him past horses with thousands more dollars on them.