Kentucky Derby’s Lucky Losers: Devil Diver (1942)

Aug 20, 2025 Jennifer Kelly / TwinSpires.com

Devil Diver and Eddie Arcaro up in the Pheonix Handicap at Keeneland. (Photo courtesy of the Keeneland Association)

Helen Hay Whitney’s Greentree Stable was a force in the first half of the 20th century, with multiple classic wins and four Hall of Famers racing in their pink silks with striped sleeves. After inheriting Greentree from her husband, William Payne Whitney, Helen partnered with her son John Hay Whitney, better known as Jock, and campaigned horses like Twenty Grand and two three-year-olds of 1942, both of whom took a shot at the Run for the Roses.

While Devil Diver may have finished behind stablemate Shut Out in the 1942 Kentucky Derby, this Greentree-bred made his name in the handicap division, turning his losing shot under the Twin Spires into a Hall of Fame career.

Homebred Brilliance

Foaled March 11, 1939, the bay colt with a dribble of white on his forehead and one short white sock, was the product of Greentree breeding: his sire St. Germans, an English-stakes winner, had already sired two Kentucky Derby winners by then, Twenty Grand (1931) and Bold Venture (1936), while his dam Dabchick won once in five starts. His name, Devil Diver, is inspired by the Pied-billed Grebe, also known as a dabchick or a devil diver, a species of waterbird native to North and South America. As a yearling, the colt joined stablemate Shut Out in the barn of Greentree trainer John Gaver for their education as racehorses.

Devil Diver broke his maiden in his fourth start and then took the Sanford and Hopeful Stakes at Saratoga before trying the Futurity at Belmont and the Remsen at Jamaica, where he finished second. His other stakes wins at two included the Breeders’ Futurity at Keeneland, where he finished ahead of future Blue Hen mare Miss Dogwood. At the end of his 1941 season, he finished with a record of 4-7-1 in 12 starts, the third-highest money earner in his division.

To prepare Devil Diver for his Kentucky Derby try, Gaver sent him to Keeneland for the Phoenix Handicap on April 9. The distance was short, only six furlongs, but the field included Whirlaway, the previous year’s Triple Crown winner. From the break, jockey Eddie Arcaro had Devil Diver on the lead but faced pressure from other horses throughout the race. Whirlaway unleashed his trademark late run in the stretch, but the Greentree colt was able to hold off the four-year-old by a head. Given the choice between Devil Diver and Shut Out in that year’s Kentucky Derby, Arcaro chose the St. Germans colt, believing that he was the stronger of the two.

Durable Superstar

The field of 15 for the 68th Kentucky Derby included Alsab, the previous year’s two-year-old champion purchased as a yearling for $700 by Al Sabath of Chicago; Shut Out, Blue Grass Stakes winner; and Devil Diver, who would have Arcaro, already a two-time Derby winner, in the saddle. Saving ground, Devil Diver was fifth early but never improved his position while Shut Out waited until the stretch to make his bid, taking over the lead inside the final quarter and winning by 2 1/4 lengths over Alsab. Two weeks later, Alsab turned the tables on both Shut Out and Devil Diver and took the Preakness Stakes.

Wheeled back to seven furlongs ten days later, Devil Diver won the Domino Handicap by a head. He won two more times in 1942 before taking a break ahead of his four-year-old season, a six-month layoff that prepared the hard-trying colt for his move up to the handicap division.

Though he wrestled with a malformed right front foot, where the inside quarter of that hoof was flat rather than concave, as a result, his heel took quite a bit of force when racing, and that forced Gaver to stop on him at times. Despite this, Devil Diver found a home in the handicap division, gradually stretching out from seven furlongs to ten and twelve furlongs. He won the Toboggan, Brooklyn, Carter, and Metropolitan Handicaps at four, beating horses like Market Wise, but came out of his try in the Stars and Stripes Handicap sore and was sidelined until the following April.

He started his five-year-old season in 1944 with five straight wins, including his second straight wins in the Toboggan and the Metropolitan. During the Saratoga-at-Belmont meet, held downstate because of wartime restrictions, he bested Princequillo to win the Whitney Stakes, named for the late husband of owner Helen Hay Whitney. Devil Diver won two more times that season, but with Shut Out already at stud for Greentree, the St. Germans colt remained in training for one more season.

At six, he took his second straight Paumanok and then his third Metropolitan Handicap. He then met Stymie in the ten-furlong Suburban at Belmont Park. Laden with 132 pounds, the short field threw what they had at the experienced handicapper, but to no avail. He took the lead from the break, repelled challenges by Olympic Zenith and Great Rush, and then stretched out his advantage even as Stymie mounted his own bid. He had two-thirds of the Handicap Triple Crown under his belt, with only the Brooklyn left. There, he would meet Stymie again and give him 16 pounds: the difference was enough to stop the Diver. Stymie passed the Greentree hope in the stretch and won by 1 1/4 lengths, denying Devil Diver his triple.

That foot became a problem again, prompting the Whitneys and Gaver to retire Devil Diver to stud at Greentree. He was a useful sire there, his daughter Make Sail winning the 1960 Kentucky Oaks, notching a victory under the Twin Spires, the place where Devil Diver himself had fallen short almost two decades earlier.

Though Devil Diver was unsuccessful in the Run for the Roses, he went on to a stellar career for the legendary Greentree Stable, still the only horse to win three Metropolitan Handicaps, a star who came close to becoming only the second horse to win the Handicap Triple Crown. His durability despite a chronic foot issue made him one of those legendary racehorses of the World War II era, his speed and talent helping him win at a variety of distances and defeat other stars of this era, including Stymie and Whirlaway.