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Every so often in the Kentucky Derby, a relatively unaccomplished 3-year-old will manage to step up on the first Saturday and May and shock the racing world with a longshot win in America's greatest horse race. In fact, that has become even more of a possibility in recent years as the Derby field now almost always has the maximum 20 horses entered. These large fields often create havoc and vastly increases the amount of racing luck needed to be successful. Below is a look at some of the highest win payouts for a $2 wager in the history of the Kentucky Derby. 1. Donerail, $184.90, 1913—After several scratches left only a field of seven in the 1913 Kentucky Derby, Donerail still managed to be completely ignored in the wagering. The son of McGee had shown little to nothing while prepping for the Derby in nearby Lexington, Ky. On Derby day, though, he managed to put it all together. The comments in the chart for the 1913 Derby say Donerail, “showing startling improvement over his Lexington form,” was restrained early under jockey Roscoe Goose, made a move on the stretch turn and then proceeded to shock the world under a drive through the stretch. Donerail would go on to add a couple of Stakes wins in Canada in his career before retiring with 10 wins in 62 starts and earnings of $15,156. 2. Mine That Bird, $103.20, 2009—The gelding was a multiple Stakes winner in Canada as a 2-year-old, but finished dead-last in the Breeders' Cup Juvenile when sent to the U.S. to conclude the year and showed little in defeat in two starts in the backwoods of New Mexico as a 3-year-old prior. However, in the Kentucky Derby, Mine That Bird rallied from far back along the rail, aided by a brilliant ride from jockey Calvin Borel and perhaps a sloppy track, to spring the second-largest upset in Kentucky Derby history. Mine That Bird would be narrowly beaten by Rachel Alexandra in the Preakness Stakes, but never managed to regain his Triple Crown form. He never won again in nine starts following the Derby and was retired. 3. Giacomo, $102.60, 2005—The son of Holy Bull entered the Kentucky Derby as an unheralded runner from California, but exited as the third-highest priced winner in the history of the race. Owned by Jerry Moss and trained by John Shirreffs, Giacomo was disregarded largely because he failed to win any of California's prep races and was off-the-board in the Santa Anita Derby. Like Mine That Bird, Giacomo was far back early in the Kentucky Derby, before mounting a wide bid on the turn that proved to be a winning one. Giacomo would go on to finish third in the Preakness Stakes and seventh in the Belmont Stakes. He is currently a stallion at Adena Springs. 4. Gallahadion, $72.40, 1940—This year's Kentucky Derby featured a heavy odds-on favorite in Bimelech, which caused the odds of the other seven horses in the race to swell. Gallahadion had managed to win the San Vicente Stakes at Santa Anita prior to the Derby, but still remained the third-longest shot on the board. Gallahadion would race prominently throughout in the Derby and surge past the field late to win by 1 1/2-lengths. Gallahadion would win five races as a 3-year-old, but the following season was 1-for-14 before retiring without ever having won another Stakes race.
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