With this year’s edition of the Kentucky Derby coming up fast, let’s look at something that a horse rarely can be entering Derby week: a maiden. With the Derby now requiring a certain number of points in order to make it into the gate, a horse will need to finish in the money in more than one race or finish second in the right races to join the cavalry charge of horses in Louisville. Before the points system became reality, a horse could come into the Derby as a real maiden; nine have done it since 1937. Their chances of winning, though, might not be as good since they may not have the experience or the talent to be the one in front at the wire at Churchill Downs.

These three maidens defied the odds and did just that, making the Run for the Roses their own.

Buchanan (1884)

In the last part of the 19th century, African-American jockey Isaac Burns Murphy won three Derbies (1884, 1890, 1891), his first on a firebrand chestnut named Buchanan.

Buchanan had not won a race prior to his start in the 1884 Kentucky Derby and was, from contemporary accounts, a difficult horse to ride. Murphy was one of the best jockeys of the day, though, and managed Buchanan well enough for the colt to break his maiden in the Run for the Roses. Buchanan went on to a record of 35: 8-14-10, winning the Ripple Stakes and the Clark Handicap before retiring at the age of three.

Buchanan stood stud at Senorita Stock Farm in Lexington, KY, the site of the present -day Kentucky Horse Park. He didn’t make much of an impression at stud, siring only three stakes winners, and died in either 1894 or 1897 (contemporary accounts differ) of an inflammation of the bowels.

Sir Barton (1919)

Sir Barton made his last start of 1918 in the Futurity at Belmont in September; he was due to make additional starts in his two-year-old season before an illness put him out of commission for the remainder of the year. Trainer H.G. Bedwell declined to start the colt in any races in the first part of 1919, though stablemate and fellow Kentucky Derby starter Billy Kelly did have three starts prior to Derby Day. Sir Barton prepared instead through a series of workouts with other horses in the Ross Stable, demonstrating just how good the three-year-old son of Star Shoot* was.

Saturday, May 10th dawned rainy and wet, with the Churchill Downs oval heavy from rain. Twelve went to the post and one left the barrier flying: Sir Barton. He led at every pole and never surrendered, not even to Billy Kelly, for whom he was supposedly there to clear the way. Sir Barton went on to follow up that spectacular win with another speedy performance four days later in the Preakness. From there, he won the Withers and then the Belmont Stakes, completing America’s first Triple Crown.

From maiden to legend in the space of thirty-two days, the most successful horse to break his maiden in the Kentucky Derby.

Broker’s Tip (1933)

Black Toney had sired a Kentucky Derby winner already, a colt named Black Gold who won in 1924. His son Broker’s Tip had shown little of the form that Black Gold had and thus no one expected to see Broker’s Tip in a stretch battle in the 1933 Kentucky Derby and the near-fistfight that broke out as a result.

Broker’s Tip’s jockey Don Meade sent his mount to the inside of frontrunner Head Play, ridden by Herb Fisher. Incensed that Meade had snuck up on him, Fisher tried to push Broker’s Tip into the rail, to which Meade responded by pushing back and attempting to pull Head Play’s saddlecloth. Fisher took a couple of swings at Meade with his whip and suddenly the two jockeys were exchanging blows as their mounts dueled down the stretch. At the wire, Broker’s Tip managed to get his nose in front, or at least that’s how the judges saw it. Fisher lodged an infraction claim against Meade, which went nowhere, and then the two continued their fight in the jock’s room. (The two made up and even came together years later to talk about that Derby.)

Both jockeys received suspensions for their rough riding in the Derby. Broker’s Tip got a trophy, the purse, and his lone win of his career, but that photo of Meade and Fisher fighting down the stretch stands more iconic than the horses involved.

These three horses show that it is possible to break your maiden in America’s most famous race. Could that happen again? Only time will tell.