Tall Tales of the Track: Alan-A-Dale Goes Trotting for Roses

Each Kentucky Derby winner comes with a unique story. Sometimes they are underestimated and make history as the biggest win bet in the storied race’s history (Donerail in 1913). Maybe they come to Louisville as the assumed rabbit for a stablemate and then prove to everyone that perhaps this horse is better than anyone could have predicted, as Sir Barton demonstrated in 1919.

In 1902, Alan-a-Dale won the roses thanks to an unconventional course of training and a savvy jockey who knew just what to do to keep the mount and score another historic victory under the Twin Spires. 

Family Traditions

Thomas Clay McDowell had a purple pedigree of his own before he even planned his breeding season at his family’s Ashland estate in Lexington, Ky. His great-grandfather was Henry Clay, a long-time senator from Kentucky who also served as Secretary of State under President John Quincy Adams. His father, Henry Clay McDowell, was a breeder of Standardbreds for harness racing, standing Dictator, one of the four sons of Hambletonian that became foundational sires for the breed. Thomas became a breeder like his father, but of Thoroughbreds rather than their trotting brethren, and also worked as a trainer for owners like William K. Vanderbilt, a founding member of the Jockey Club. But McDowell is most famous for the horses he bred and raced in his own colors.

At Beaumont Farm stood Halma, winner of the 1895 Kentucky Derby, the last contested at 1 1/2 miles, whose wins in the Run for the Roses, the Latonia Derby, and the Clark Stakes made him an ideal fit for McDowell’s mare Sudie McNairy. A record setter at Washington Park in Chicago, the chestnut mare had also produced Maid Marian, who set a record for a mile and 20 yards at the same racetrack for McDowell. In 1899, Sudie McNairy’s cover by Halma produced a splashy chestnut colt that the breeder/owner named Alan-a-Dale (also spelled Allan-a-Dale in other sources), his name honoring McDowell’s fondness for the story of Robin Hood.

From the start, Sudie McNairy’s colt stood out from his peers. The Morning Telegraph described him as “a good, big, wiry, well-grown colt. He will make a big horse, and one of a great deal of quality.” McDowell thought so much of him that he turned down several offers for Alan-a-Dale during his two-year-old season, including one for $20,000, but the breeder/owner, who also trained the colt, was not willing to part with him. In his juvenile season, he won three of four races, including the Brighton Junior Stakes at Brighton Beach Race Course in New York. By mid-October, the Daily Racing Form reported the colt had been turned out for the winter, with McDowell’s eye on the great three-year-old stakes in 1902. 

Winkfield’s Winning Ways

Compared to other top two-year-olds of 1901, including the filly Endurance By Right, who started 18 times and won 16, Allan-a-Dale’s first season on the track was rather brief. The reason for this was simple, but one that would not have been clear from accounts of his on-track exploits: he had bad legs, a lingering injury from trying to jump a fence as a yearling, keeping him from being as durable as some of his peers. Fortunately, jockey Jimmy Winkfield was more than aware of the flashy chestnut’s faults.

The prominent African American rider, who won the 1901 Kentucky Derby on His Eminence, had worked Alan-a-Dale in the spring as McDowell prepared the colt for his first start of the year, which happened to be the Kentucky Derby. An injured knee led the young breeder/owner/trainer to keep the colt in shape by working him pulling a sulky, the small carts used in harness racing, rather than carrying the weight of a rider. McDowell would only put a saddle on the colt occasionally, and more than once, the man in the saddle was Winkfield. He knew what Alan-a-Dale was capable of and wanted to ride him in the Derby, but the stable’s primary jockey was Nash Turner, who would have his choice of either The Rival, McDowell’s other good three-year-old, or the son of Halma. Winkfield purposefully held Alan-a-Dale back in several workouts, and that perceived slowness prompted Turner to choose The Rival. Winkfield would get the nod for Sudie McNairy’s colt.

The 1902 Kentucky Derby came during the race’s nadir, a decade-plus downturn with small fields and even smaller purses. But the Derby was still a race with value, and McDowell arrived in Louisville with both The Rival and Alan-a-Dale. They faced only two others on Derby Day: Abe Frank, the favorite who would win the Tennessee Derby, and Inventor, a longshot. Winkfield had an advantage over his fellow riders: not only was he familiar with Alan-a-Dale, who he knew the others would not pay much attention to, but he also knew the racetrack itself. He knew that the surface was covered in sand when it was not in use, and then crews pushed the sand to the outside during the season. The legendary jockey put that to good use in the Derby.

Because Abe Frank’s jockey Monk Coburn was eyeing Nash Turner on The Rival, Winkfield was able to keep Alan-a-Dale out of trouble on the lead, slowing the pace down to save his colt for the race’s end. But he felt his mount bobble, and he knew he was going to have to do something drastic to pull off the win. Each time a horse got close to Alan-a-Dale, Winkfield would push them wide out into the sandy areas of the racetrack, and then he would push his mount back to the rail. He was able to save enough of Alan-a-Dale for the finish, holding off Inventor by a nose. “When it was over, it was a sight worth going a thousand miles to see,” author John L. O’Connor wrote in his "History of the Kentucky Derby 1875-1921." “It seemed as though everybody was looking for the popular owner, T.C. McDowell, to shake him by the hand and congratulate him.”

For his ride, Winkfield got a $1,000 bonus and the unfortunate title of being the last African American rider to win the Kentucky Derby, as Jim Crow laws and other efforts drove black horsemen out of the sport. Though he was victorious, Alan-a-Dale came away from his valiant effort with an injury that prevented him from running again in 1902, meaning that this Kentucky Derby winner’s only start and win at three was in the big race. He would race again at age four and ended his career in 1905 with 17 wins in 37 starts and then stood stud at McDowell’s Ashland. He would go on to sire a Kentucky Oaks winner in Ellen-a-Dale and live until 1925, passing away at an Illinois farm where he stood as a sire for hunters and jumpers.

Winkfield would move on from riding in the United States and find his fortunes as a jockey and then trainer in Europe, the last of those early African American riders to find success under the Twin Spires and beyond.