Two American sports legends made their respective debuts during the summer of 1914. One was Babe Ruth, who at the time was a promising pitching prospect with the Boston Red Sox. The other was Regret, a four-legged phenom who spent two weeks that August establishing a reputation as a force to be reckoned with on the dirt oval at Saratoga Race Course. Ruth would punch his ticket to Cooperstown with an iconic career of walloping tape-measure home runs and breaking records with the New York Yankees. Regret, meanwhile, also became a Hall of Famer, securing her position in racing history as the first filly to win the Kentucky Derby.
But before she became a national sensation by winning the 1915 Run for the Roses at Churchill Downs, the New Jersey–bred Regret took the racing world by storm with three standout performances in 14 days at the Spa as a 2-year-old. Bred and owned by Harry Payne Whitney and trained by Hall of Famer James Rowe, Sr., Regret made her debut in the Saratoga Special on August 8, 1914. As the lone filly in the field eight, the chestnut daughter of Broomstick (winner of the 1904 Travers Stakes) stood out from her rivals. With “speed in reserve,” according to her Daily Racing Form past performances, Regret, with jockey Joe Notter in the irons, earned a stylish maiden-breaking victory by a length.
Regret’s Saratoga Special win, however, didn’t exactly produce big headlines. The race took place on the undercard of the Travers Stakes, which was won by Hall of Famer Roamer in record time. The New York Times reported that “The brilliant performance of Roamer was the occasion for long applause after the little bay horse returned to the scales, and Regret’s victory was also heartily applauded.”
Seven days later, Regret was the headliner at Saratoga as a “handy winner of the Sanford Memorial,” according to the Times. She was once again the only filly in a field of eight and carried top weight of 127 pounds to win by 1½ lengths “under restraint throughout.” The Times heaped plenty of praise on Whitney’s prized filly, stating she was “the same queenly lady that she was in the Saratoga Special.”
A week later, Regret was back at it. Saddled with a field-high weight assignment of 127 pounds, she entered the Hopeful Stakes against 10 colts. On a track described by the Timesas “heavy from recent rains and a particularly trying one over which to race,” Regret was positioned in the middle of the field for much of the six furlongs. Taking aim at the leaders in the stretch, the Whitney filly “had a long, hard chase, but she was equal to the task.”
With that, Regret became the first horse to win Saratoga’s trio of major 2-year-old stakes; only the colts Campfire (1916), Dehere (1993), and City Zip (2000) have since accomplished the feat. And then she wasn’t seen on a track again for nine months.
On the second Saturday of May 1915, following a hiatus of 259 days since her Hopeful victory, Regret was at Churchill Downs for the Kentucky Derby with a record crowd estimated at 49,000 in attendance.
Regret was sent off as the moderate favorite against 15 foes in the Derby. The lone filly in the field for the fourth time in as many starts, Regret quickly made the lead. Pebbles, an old rival from Saratoga, sat just off the pace and tracked Regret throughout the 1¼-mile contest. Pebbles made a move for the lead in the final quarter, but Regret once again displayed her superiority and won by two lengths in 2:052⁄5. Prior to Regret, 29 fillies had tried and failed to win the Kentucky Derby; since then, only Genuine Risk (1980) and Winning Colors (1988) have joined the mighty Regret as heroines of America’s most famous horse race. And to think, it all started in Saratoga.
