The largest win payoff did not come when Mine That Bird won the Kentucky Derby in 2009. It came in 1913 when Donerail won the Kentucky Derby and paid $184.90 for a $2 win wager.
The lowest payoff for a $2 win wager has happened twice. It first occurred in 1943 when Count Fleet won the Derby and returned $2.80. It happened the second time, five years later, when Citation wore the roses in 1948.
Before pari-mutual wagering was introduced in 1908, three winning horses went off at odds of 1-3 (a return of about $1 for every $3 wagered)—Hindoo in 1881, Halma in 1895, and Agile in 1905.