Modern horse racing fans in America naturally think of the Triple Crown races as a set: that a talented three-year-old’s connections will view the Crown as its own goal, rather than three separate opportunities. Certainly, in recent decades, the races have been marketed that way, with each successive Kentucky Derby winner immediately becoming the subject of the question, “But can he win the Triple Crown?”
However, this was not always the case. The concept of the American Triple Crown is far younger than the races themselves; the races were not connected to each other until the 1930s, while the Kentucky Derby, Preakness, and Belmont originated in 1875, 1873, and 1867, respectively. In many years in the early part of the 20th century, the Kentucky Derby and the Preakness dates were so close that contesting both would not have been possible; in fact, in 1917 and again in 1922, the two races were held on the same day.
The Triple Crown exploits of the father-son duo Gallant Fox (1930) and Omaha (1935), however, caused racing connections in America to start looking at the races in a manner similar to how the British viewed the Two Thousand Guineas, the Derby Stakes, and the St. Leger (the races that make up the Triple Crown in England).
The concept became wildly popular, and over the next decade and a half, five horses won the Triple Crown (War Admiral in 1937, Whirlaway in 1941, Count Fleet in 1943, Assault in 1946, and Citation in 1948). Although there was a 25 year gap between Citation’s sweep and that of Secretariat, the series remained a primary goal for three-year-olds.
In the post-Secretariat era, the Triple Crown is still America’s top racing prize, but there have been a few cases of Kentucky Derby winners who have chosen not to contest the Preakness Stakes. You can find a complete list of past Preakness winners here: twinspires.com/preakness-stakes/winners
Gato del Sol (1982)
A gray son of *Cougar II, Gato del Sol was a surprise winner of the Kentucky Derby due to his deep closing running style and unimpressive prep races. After winning the Derby, his connections were in agreement that the Preakness was unlikely to suit Gato del Sol, and they believed that they would have more success in the Belmont Stakes.
Gato del Sol got second in the Belmont, but it was a very distant second behind the dominant Conquistador Cielo, who would eventually be named Horse of the Year. Gato del Sol would meet up with Conquistador Cielo again in the Grade I Travers Stakes that summer, along with Preakness winner Aloma’s Ruler, but all three were bested by longshot Runaway Groom.
Gato del Sol continued to race until age six, and although he had several good races, he never again won a graded stakes race.
Spend a Buck (1985)
Spend a Buck’s modus operandi was as different from that of Gato del Sol as two Thoroughbreds can get. His running style was to go immediately to the lead and hold on for dear life, a tactic that made him formidable in the inaugural Breeder’s Cup Juvenile in 1984. He earned a respectable third in that race and was pointed toward the Triple Crown.
That year, Garden State Park in New Jersey announced a million-dollar bonus to any horse who could win the Cherry Hill Mile Stakes, the Garden State Stakes, the Kentucky Derby, and the Grade III Jersey Derby. Spend a Buck’s connections saw this as a lucrative opportunity for their colt, who cruised through the first two Garden State races and then ran the Derby competition off their feet, winning by over five lengths.
Trainer Cam Gabolati’s declining of a Triple Crown pursuit in favor of the easier and richer Jersey Derby prompted the creation of the Triple Crown Challenge (sponsored first by Chrysler and later by Visa), which not only provided for a million-dollar bonus to the horse who performed the best in all three Triple Crown races but also a five million dollar bonus for any horse who won the Triple Crown. The five million went unclaimed, and Visa ended the sponsorship in 2005.
Spend a Buck, however, won both the Jersey Derby and his million-dollar bonus. He was second to Skip Trial in the Grade II Haskell Invitational, but secured Horse of the Year honors with a win against his elders in the Grade I Monmouth Handicap.
Grindstone (1996)
Unlike the uproar that came about when Spend a Buck skipped the Preakness, Grindstone’s reasons for missing the Preakness Stakes were straightforward. Four days after his dramatic closing rush in the Kentucky Derby, resulting in a winning margin of a few inches, Grindstone was discovered to have bone chips in his knee.
He was immediately retired to stud, where he had moderate success. His best offspring by far was 2004 Belmont Stakes winner Birdstone, himself the sire of 2009 Kentucky Derby winner Mine that Bird and 2009 Belmont Stakes winner Summer Bird.
Country House and Maximum Security (2019)
The 2019 Triple Crown season was an odd one. Two horses could claim some form of Derby victory, and neither one of them ran in the Preakness.
Disqualified Kentucky Derby first-place finisher Maximum Security was eliminated from Preakness consideration by his irate owner, Gary West, who felt his colt had been a deserving winner. Maximum Security later finished second in the Pegasus Stakes but then rattled off victories in the Grade I Haskell Invitational, Grade III Bold Ruler Handicap, and Grade I Cigar Mile to be named champion three-year-old.
Official winner Country House was said to be doing well immediately after the Kentucky Derby, but he developed a cough in the days after and required antibiotics and treatment from the nation’s premier equine hospital, Rood and Riddle. After finishing the medications, trainer Bill Mott tried to get Country House back to the racetrack, but it was discovered that the horse suffered from bone bruising and was beginning to develop laminitis, necessitating his retirement.
Mandaloun (2021)
It is likely that had Medina Spirit’s disqualification come quickly and not been contested, Mandaloun would have run in the Preakness. However, when trainer Brad Cox announced his intention to rest Mandaloun to save him for a fall campaign, he was not technically a Derby winner yet. That proclamation came at the end of 2021, by which time Mandaloun had added the Pegasus Stakes and the Haskell Invitational to his resume.
While the Kentucky Derby winner does not always automatically run in the Preakness Stakes, skipping the second jewel, as shown above, is often a source of controversy and drama.