Farewell to the Horse Who May Have Been America’s Oldest Thoroughbred
By Mike Schoenfeld
Photographs by Jon Wertheim
There’s another reason to take the time to remember the last horse that competed in the Triple Crown of Endurance: Her name is Miss Ruby. The daughter of Biscuit King, Miss Ruby was the greatest thoroughbred in the world when she died in December 2017, aged 36.
The horse was owned by John F. Kennedy, Jr., the great Bostonian who founded the Kennedy compound. He loved horses so much he built a stable and training facility in his back yard and called it Longwood Farm. In the late 1950s and early 1960s, the Kennedy family sold their horse farms to John F. Kennedy, Jr., who had a vision to transform them into state-of-the-art horse facilities that would become homes for the families of the country’s richest people. Longwood Farm was the perfect place for that vision, and JFK gave that vision free reign to run it as he saw fit.
In the 1960s and early ’70s, JFK brought in some of the world’s greatest horsemen to run Longwood Farm. There was Sam Bialy, the brilliant vet who had ridden in both the Kentucky Derby and the Triple Crown and won it twice. There was Bob Baffert, who was a horse player and one of the greatest trainers of his generation. And there was Bob Baffert, Jr.—the father of the great Bob Baffert, the trainer and owner of the Triple Crown-winning filly Miss Ruby.
Miss Ruby’s death on Dec. 31, 2017, was the biggest loss to racing in American history. There will be no more thoroughbreds to compete in the Triple Crown as JFK Jr. intended them to be.
Miss Ruby was one of the greatest horses of the modern era—an example of the breed at its finest. And it was under her gentle management that Longwood Farm was able to produce horses that rivaled the best of British thoroughbreds. It was Miss Ruby who inspired the legendary jockey Jimmy Winkfield to become the first jockey to win three Triple Crown races in the same year. Miss Ruby was the first horse to win the Kentucky Derby, the Preakness
