April 2026 Issue

April 2026 | EAST COAST EQUESTRIAN 34 Of Timber & Trees The Maryland Hunt Cup as Family Business Continued from page 29 Hunt Cup, finishing sixth on Whackerjack after her 1968 legal victory against theMarylandRacing Commission.Womenwere not formallywelcomed into the race until 1979, when Toinette Neilson rode. Slater’s win the next year completed the arc. Cancottage would go on to become one of the great timber horses of the era, winning the Hunt Cup three times—in 1980, 1981, and 1983—with Slater aboard for the first two. Both Kusner and Slater had entered timber racing with substantial show-jumping mileage behind them, another re- minder that the Hunt Cup’s family tree intersects constantly with the wider horse world. Smith “He scared me,” Tommy Smith said of the plain Thoroughbred he claimed in 1962 for $1,250. “He took off with me and I was strictly a passenger.” The horse was Jay Trump, and few Hunt Cup stories better show how an unlikely champion can emerge from humble beginnings. Smith himself came from foxhunting stock. His father, Crompton Smith Jr., rode early American steeplechases, including the inaugural Carolina Cup, and his grandfather, HarryWorcester Smith, was an internationally known foxhunter and sport- ing writer whose work helped shape American hunting culture. Tommy firstmade hismark bywinning the 1959 Hunt Cup on Fluctuate, owned by H. Robertson Fenwick. Soon after, recovering from a separated shoulder, he went scouting for inexpensive pros- pects at Charles Town and found a plain 16.2-hand Thoroughbred offered for claiming. That horse became Jay Trump, later called by Peter Winants “the most versatile steeplechaser of the era, maybe ever.” Preparing for the 1963 Hunt Cup, Jay Trump’s boldness was already evident. “Sometimes he stood off the fences two or three strides,” Smith said. “At the twelfth he stood back so far he landed on the top rail with his girth.” Jay Trump still set a new course record of 8:42 1/5. By 1966, Jay Trump and Mountain Dew were both chasing their third Hunt Cup victory and the race’s Fourth Challenge Cup. Smith planned the race as Jay Trump’s final timber start. “We challenged Mountain Dew at the sixteenth,” he said. “I knew we had too much horse for him this time.” Smith and his former claimer galloped home eight lengths clear, retiring the trophy. Smith trained Jay Trump throughout his career and rode him to two of his three Hunt Cup victories. Smithwick “He always tried—gave you his best,” Mikey Smithwick said of his brother Paddy. “Some riders quit on you after a couple of fences. Not Paddy.” The Smithwick brothers, Alfred Patrick “Pad- dy” and Daniel Michael “Mikey,” grew up at the Elkridge-Harford Hunt Club, where their father, an Irish immigrant, served as huntsman and sta- ble manager. From that hunt-country foundation emerged two of the most influential figures in American steeplechasing. Mikey’s big chance came in 1956, when he be- came trainer for Mrs. Ogden Phipps, whose stable soon became one of themost powerful in the sport. Within a year the operation produced 38 winners and $220,000 in earnings—nearly 30 percent of the available steeplechase purse money. Between 1957 and 1970, Mikey was leading trainer twelve times, saw career earnings exceed $4.5 million, and developed three future Hall of Fame horses: Neji, Jay Trump, and Ben Nouvel. Meanwhile Paddy built one of themost respect- ed riding careers in American steeplechasing. Riding professionally from 1946 to 1996, he won nearly 400 races and five national championships, despite standing an unusually tall 5’10” for a stee- plechase jockey. “He had a great sense of pace,” Mikey recalled. “Marvelous timing into and over fences. And what hands.” The A.P. SmithwickMemorial steeplechase, run each August at Saratoga, now honors that legacy. Casting the Widest Shade “Foxhunting is not a sport for a season; it is a way of life.” — Nancy Penn-Smith Hannum That way of life is the quiet foundation beneath theMarylandHunt Cup and the families who have shaped it. Within the long history of the race, two lineages stand out as the architecture behindmuch of its story: the Fenwicks and the Penn-Smith/ Hannum family. The Fenwicks represent the most visible trunk of the sport’s family tree, touching nearly every dimension of theHunt Cup itself.ThroughCharles C. “Cuppy” Fenwick, who served as secretary of the race for three decades, and his sonCharlie Fenwick Jr., a five-time winning rider and six-time winning trainer, the family’s influence extended from the saddle to the stable to the governance of the race. Their lineage reaches even further through the Stewart family, linking them to the Hunt Cup’s founding generation. If the Fenwicks have often been the race’s most visible dynasty, the Penn-Smith/Hannum family represents a more quietly woven network across the broader hunt-country world. Beginning with Nancy Penn-Smith Hannum, the legendary Master of Mr. Stewart’s Cheshire Foxhounds, the family bridged the foxhunting traditions of Vir- ginia, Pennsylvania, and Maryland—traditions stretching from the timber courses of Maryland and Pennsylvania to the storied hunt country of Middleburg, Virginia. That foxhunting culture has donemore thanpro- duce riders and timber horses. Across this tri-state hunt country, conservation easements, land trusts, 1980 Maryland Hunt Cup winner Joy Slater (center) with owner Mrs. Miles Valentine (left) and trainer Jill Fanning (right). The victory of Valentine’s Cancottage marked the first time a woman won the race and stands as a vivid example of the Hunt Cup’s family-driven tradition, where owners, trainers, and riders often come from the same intertwined hunt-country community. Courtesy of the Alex Brown archives. Continued on page 38