Biggest Longshots to Win at the Kentucky Derby

Bourbon, big hats and bluegrass are the hallmarks of the Kentucky Derby. But then, so are big bets and longshots. Of the 14 longshots that have won the Run for the Roses, four of them had 21/1 odds, meaning you’d have walked away with a very nice profit on a win ticket and would be taking everyone to dinner if you had the winner in an exacta or trifecta.

Longshots with 21/1 odds or higher have won the Derby nearly 10 percent of the time, dating back to the first race in 1875, and more than a third of those winners (five) have won the roses since 2002. But more recent history is different: five consecutive betting favorites have won the Kentucky Derby. Time for another longshot?

Post time for the 144th Run for the Roses is 6:34 p.m. ET and NBC will provide live television coverage. More than half of the 20 horses entered in Saturday’s race face taller odds to win — in fact, 11 horses have odds higher than 25/1. If any of these five major longshots win, they would vault high on this list below (check here for latest odds): Firenze Fire (50/1), Lone Sailor (50/1), Instilled Regard (50/1), Bravazo (50/1) and Combatant (50/1) from the 20th gate. The favorite is Justify, currently at 3/1.

Kentucky Derby long shots: We at Sports Handle love the underdog, so below is a list of horses to wear the roses after overcoming tall odds

91/1 Donerail (1913): The biggest longshot to ever win a Kentucky Derby, jockey Roscoe Goose was off the lead, but within striking distance the entire race and won by half a length. He set a track record with at that time with a time of 2:04 4/5. Secretariat currently holds the Kentucky Derby record his 1973 run of 1:59 2/5.

50/1 Mine That Bird (2009): This horse didn’t just win the Derby, he went from eight lengths back to win by 6 ¾ lengths on a muddy track. Mine That Bird is one of only nine geldings to win the Run for the Roses and he went on to finish second at the Preakness and third at the Belmont.

50/1 Giacomo (2005) : Tied with Mine That Bird as the horse with the second longest odds to win the Derby, Giacomo earned owner Jerry Smith the biggest check in the history of the race – $1,639,600. He went on to finish third at the Preakness and seventh at Belmont. He was retired to stud in 2006 and stands in Oregon.

35/1 Gallahadion (1940): The son of Reigh Count, the mare that won the Derby in 1928, Gallahadion had little success going into the Derby and little after, but on that day in 1940, got his 15 minutes of fame. The horse was owned by Ethel M. chocolate magnate Ethel Mars, who couldn’t attend the race due to a cold. Gallahadion was third in the Preakness and didn’t place at Belmont.

31/1 Charismatic (1999): On a slow track, Charismatic won by a head and then went on to win the Preakness. But what most remember about this horse is the Belmont – where he was in the lead in the stretch before pulling up painfully lame. Charismatic broke his foreleg during the race and the image of jockey Chris Antley gently cradling his leg post-race is one of the most moving and enduring in sports. Charismatic healed, never raced again, and was named 1999 Horse of the Year.

30/1 Proud Clarion (1967): Posting what was then the third-fastest Kentucky Derby time, Proud Clarion was fifth entering the homestretch, where he and jockey Bobby Ussery made a move between the second- and third-running horses and ultimately won the race by a length. He went on finish third in the Preakness and fourth at Belmont before being retired to stud.

[Be sure to check out: Kentucky Derby Preview and Picks for 144th Run for the Roses]

29/1 Exterminator (1918): Referred to as “that truck horse” or “that goat” by his owner, Exterminator only got to Run for the Roses because the horse in his stable he was bought to help train developed ringbone. Exterminator hadn’t raced in two years, but he went ahead and, ahem, exterminated, the competition, winning by a length. The horse went on to race until he was nine, before being retired for leisure.

25/1 Thunder Gulch (1995): In a year when owner D. Wayne Lukas entered three horses in the Derby, Thunder Gulch did him proud, winning not only in Kentucky, but at the Belmont, too. He finished third at the Preakness. He stood at stud until 2015 and before his death in March of this year, was a companion horse to Triple Crown winner American Pharoah.

Kentucky Derby long shots: We at Sports Handle love the underdog, so below is a list of horses to wear the roses after overcoming tall odds — Thun-der!

25/1 Dark Star (1953): Even jockey Hank Moreno was surprised to win. Saying after the race that he had hoped to finish third, Moreno rode Dark Star behind the field until the backstretch, when he found an opening and held off 3/5 favorite Native Dancer by a head. His racing career ended at the Preakness, where he injured a tendon while finishing fifth.

24/1 Stone Street (1908): A wet track was all Stone Street, who had never won a graded stakes race, needed to become a surprise winner at the Derby. In fact, the wet track must have been perfect for him, as he never won a major stakes race again. The winning time of 2:15 1/5 remains the slowest in history.

21/1 Animal Kingdom (2011): In his first race on dirt with an unfamiliar jockey, Animal Kingdom ran to a 2 ¾-length victory. Jockey John R. Velazquez ended up on Animal Kingdom after his mount fell ill and Animal Kingdom’s planned jockey was injured. The horse went on to win two more stakes races, the 2012 Gulfstream Park Allowance and 2013 Dubai World Cup.

21/1 War Emblem (2002): In an ironic twist of fate, War Emblem won the Derby as a longshot and went on to win the Preakness, before stumbling out of the gate Belmont and finishing behind a 70/1 longshot. Jockey Victor Espinoza hadn’t even seen the horse until the morning of the Kentucky Derby. War Emblem stood at stud in Japan from 2002-15 and sired only 119 foals. Back in the U.S., Animal Kingdom stands at stud for $30,000 in Kentucky.

21/1 Gato del Sol (1982): This horse may be better known for what he didn’t do – race in the Preakness – than for his Derby win. Gato del Sol was in the back of the 19-horse pack early in the race, but inched his way into the running and ultimately won by 2 ½ lengths. His owner then skipped the Preakness, marking the first time in nearly a quarter century that a Derby winner didn’t run the Preakness. He went on to finish second at Belmont.

21/1 Bold Venture (1936): Bold Venture survived an incredibly messy Derby start to win, but the win didn’t convince anyone that the horse – who had never before won a stakes race – or the jockey – who was an apprentice – were worthy. But after going on to win the Preakness, as well, some minds were changed. Bold Venture retired after his Preakness win with a bowed tendon. He went on to sire Triple Crown winner Assault (1946) and Derby and Belmont winner Middleground (1950).