Kentucky Farm Time Capsule: Castleton’s Prowess Touched Three Breeds

by | 01.09.2019 | 5:14pm
Undated lithograph showing a bird's eye view of Castleton. The front columns of its 1840 mansion house are visible in the upper left portion of the picture

Many subjects of our Kentucky Farm Time Capsule series thus far have seen their development mirror that of Lexington as the top Thoroughbred nursery in the country. The oldest Thoroughbred farms may sometimes trace their roots to a family homestead in the late 1700s, maybe to use as pastureland for cows, and then make the switch to racehorses, never to look back. Castleton Farm (now known as Castleton Lyons) saw top horses of at least three different breeds fill its pastures, and it distinguished itself in more than one sport.

The property now located at the corner of Newtown Pike and Iron Works was established in 1793 by Virginia native John Breckinridge, who purchased 2,467 acres. Breckinridge named the property Cabell's Dale, presumably for his wife's family. Mary “Polly” Cabell was part of a prominent political family in Virginia's early history, and Breckinridge himself would go on to serve in Kentucky's legislature and the U.S. Senate before becoming U.S. Attorney General under Thomas Jefferson.

Breckinridge grew corn, wheat, hay, and hemp on the property, and also started a Thoroughbred breeding operation, mixing English and American bloodlines. Upon the marriage of his daughter Mary Ann to David Castleman, Breckinridge gifted the couple a portion of Cabell's Dale which they renamed Castleton Farm. Castleman, who came from a long line of horsemen himself, built a Greek revival mansion on the farm in 1840 (which still exists today) and grew to love the land. Tragedy struck in 1816 when Mary Ann died giving birth to the couple's first child. When the child died too, Castleman and the Breckinridges engaged in a nasty legal battle over the property.

Ultimately, one of Castleman's sons from a later marriage would own the property and introduced Saddlebreds to the mix at Castleton. By the late 1800s, Castleton included two training tracks, 100 stalls, and even its own equine hospital. It was the perfect property for James R. Keene, who by then had enjoyed success in the Thoroughbred business as the owner of 1879 Belmont Stakes winner Spendthrift and 1881 Grand Prix de Paris winner Foxhall (the first American horse to win the race). Keene lent his Wall Street funding to Castleton and made it one of the most prominent studs in Kentucky. According to a 1996 feature in Spur magazine, Castleton owned or bred 113 stakes winners between 1893 and 1911. Keene purchased brilliant but short-lived Domino, who sired Commando, sire of Peter Pan and Colin. The vision of Keene and manager Maj. Foxhall Daingerfield had a strong influence on Col. E.R. Bradley and therefore Idle Hour, another bloodstock force of the time.

When gambling was briefly outlawed in New York in 1910, Keene began looking for a buyer for Castleton. He found interest in New York merchant David Look, and the old legend went that in their negotiations over the purchase, Look became frustrated at Keene's lack of documentation for the farm. Look wanted a surveyor's accounting of the real estate and acreage. “I understand that, Mr. Look,” Keene is supposed to have said. “But you're not buying real estate and acreage. You're buying Castleton.”

Look constructed the now-iconic stone fence that surrounds Castleton, and turned the farm's interests more intently to Standardbreds. Look struck gold when he bought broodmare Emily Ellen, who produced 14 foals, most of whom proved influential on the breed. She was second dam of Spencer, 1928 Hambletonian winner.

A Standardbred yearling takes exercise at Castleton in July 1966

By the mid-1940s, Look had run into financial woes. Castleton's fences were falling down; its barns were dilapidated. Frances Dodge Johnson, daughter of John Dodge of the automobile fortune, spied a diamond in the rough.

Dodge had been riding Saddlebreds from a young age after the activity was prescribed by her doctors as physical therapy for a hand injury. She started a breeding program in her early twenties, and had three World Champion mares as her foundation. Dodge (who eventually remarried to Frederick van Lennep in 1949) bred Wing Commander at her Michigan base and transferred the World Champion Five-Gaited stallion to Castleton to begin his stud career. Dodge also began dabbling in Standardbreds in the mid-1940s, using an eye for conformation to pick out future successes. Castleton-breds won Horse of the Year, Hambletonians, and Little Brown Jugs. All the while, she repaired barns and fences and built a brick stallion barn which is still used today, restoring Castleton to a new level of glory. Bret Hanover, winner of 35 straight races in the 1960s, would stand stud there, as would champion pacers Niatross and Abercrombie (sire of winners of $100 million).

A Saddlebred is spotted leaving a Castleton barn in August 1962

The van Lenneps could not be talked into bringing Thoroughbreds back to the property, however. The feature in Spur suggests van Lennep was teased by Thoroughbred stalwarts for her involvement in the flashy Saddlebreds, which left a bad taste in her mouth. “Harness horses were a lot more fun,” she said. “You could go out and drive them. With a Thoroughbred, you'd watch him run a mile and go back to the barn and talk about what a helluva horse he was.”

After Frederick's death in 1987, the farm was managed by John Cashman Jr. in the name of a family trust for more than a decade.

When Castleton came up for sale in 2000, a horseman once again saw potential in the property. Dr. Tony Ryan, owner of Europe's Ryanair and Lyons Demesne in Ireland, had not been looking for such a large property, according to a 2003 Keeneland magazine feature, but the chance to buy the legendary Castleton was too good to pass up. Ryan added his own style to the property, refurbishing some barns and importing the enormous and intricate iron gates at the farm's entrance from a fruit and vegetable market in London. He also changed the farm's name to its modern-day moniker of Castleton Lyons.

Since Ryan's takeover, Castleton Lyons has stood Malibu Moon, Bernstein, Wiseman's Ferry, Gio Ponti, Justin Phillip, and others. Current president Shane Ryan took over upon his father's death in 2007.

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