To illustrate my point, I ask you to join me in trying to name the best Jockey Club Gold Cup winner of each of the 11 decades the race has been run.
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Determining the best winner of the 1920s is fairly easy as well. Kummer and Glen Riddle Farm returned the next year with Man o' War. Thanks go to owner Harry Payne Whitney that year however, for entering his Damask and preventing a walkover for Man o' War, who still won by 15 lengths. Glen Riddle would later win the 1925 and '26 Gold Cups with Altawood and Crusader respectively and again in 1938 with War Admiral, who had won the Triple Crown the previous year.
Well that makes finding the best Jockey Club Gold Cup winner of the 1930s easy you say? Not so fast. In 1930, trainer Sonny Jim Fitzsimmons won his second Gold Cup with Gallant Fox, the second Triple Crown winner after Sir Barton in 1919. In fact, it was sportswriter Charles Hutton who coined the pharse "Triple Crown" that year in writing about Gallant Fox sweeping the Kentucky Derby, Preakness and Belmont Stakes. The Bel Air Stud-owned 3-year-old won nine of his 10 starts that year, losing only in the Travers to Jim Dandy. Gallant Fox also went on to become the only horse ever to sire a Triple Crown winner when his son Omaha won the title in 1935.
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His next start would be a losing one in the famous match race against Seabiscuit in the Pimlico Special.
Finding the best Jockey Club Gold Cup winner of the 1940s is also intriguing with two Triple Crown winners in Whirlaway and Citation.
Whirlaway won 32 of 60 career races including my favorite, an allowance between the 1941 Preakness and Belmont Stakes. As a 3 year old, he was second to Market Wise by a nose in the 1941 Gold Cup before winning the next year with the legendary George Wolf aboard. He was Horse of the Year in both 1941 and '42.
Citation won 32 of 45 career starts, but bested Whirlaways Triple Crown trivia note by throwing in a stakes victory at Garden State Park between the May 15 Preakness and June 12 Belmont of 1948. He was the Champion 3-Year Old Male, Champion Handicap Horse and Horse of the Year in 1948 and the last Triple Crown winner before Secretariat.
Nashua is perhaps the best horse to win the Gold Cup in the 1950s, having won it in 1955 and again in 1956 in the final race of his career. Only a runner-up finish in the Kentucky Derby away from being a Triple Crown winner, Nashua has a couple of interesting Gold Cup distinctions in that jockey Eddie Arcaro and trainer Jim Fitzsimmons are both JCGP record holders for most wins. Arcaro won the race ten times between 1935 and 1961. Fitzsimmons took home seven Gold Cups between 1929 and 1956.
Although Kelso was easily the best of the Gold Cup winners in the 1960s, four others were named Horse of The Year including Roman Ruler in 1965, Buckpasser ('66), Damascus ('67) and Arts and Letters in '69. And although it is easy to determine who was the best Gold Cup winner of the 1960s, to find the best of the 1970s is quite the challenge.
Forego, winner of the 1974 Gold Cup, won the Eclipse Award for Outstanding Older Male Horse four times between 1974-'77 and was Horse of the Year for three years straight: 1974, 1975 and 1976. Yet another Triple Crown winner in Affirmed ended his 29-race career with a thrilling 1978 Gold Cup victory over Spectacular Bid and Coastal and perhaps the best Jockey Club Gold Cup of all time saw Exceller become the only horse to defeat two Triple Crown winners in the same race when he took the 1978 Gold Cup over Seattle Slew and Affirmed.
John Henry, Slew o'Gold and Easy Goer are among the Gold Cup victors in the 1980s and Cigar probably gets the nod for the best of the 1990s. Curlin won consecutive Jockey Club Gold Cups in 2007 and 2008 to be considered the best of this decade so far, but only time will actually give us that answer.