In the spring of 1912, by the small town of Red Bank, NJ, a legend was born into the Harry Payne Whitney stable. There had been much anticipation for this foal, as it was by the mighty stallion Broomstick out of the great mare Jersey Lightning. The foal was a filly. The owners, slightly disappointed, named her Regret… as in, they regretted she wasn’t a colt. How they would change their tune in the years to come.
Trainer Jim Rowe saw something special in the blaze faced chestnut filly. He brought her along slowly and carefully, and thought her to be the best of the Whitney yearlings in 1913. Regret was to make her first start as a 2 year old at the Saratoga meet of 1914. From her very first race, Regret was tested. Instead of a maiden or allowance race, she went out to start in the Saratoga Special, where she would go against colts, including the season’s top 2 year old Pebbles. She entered as co-favorite based on her reputation for fast works, and she did not disappoint. Jockey Joe Notter sent Regret straight to the front and there she stayed, winner by a length over Pebbles and the rest of the field.
Her next race would be the Sanford Memorial only a few days later, and this time she would be under an impost of 127 lbs. The weight did not seem to have any effect on the filly, and she sauntered home half a length in front of the rest of the field. A week later she went postward for the Hopeful Stakes, again carrying 127 lbs, this time in a deep and muddy track. After getting boxed in on the rail, Regret prevailed. She won by half a length, giving thirteen pounds to the second place horse, while Pebbles finished third.
Having won three stakes races in the span of only 14 days, Whitney and Rowe took Regret home to rest and wait for her 3 year old season. She was the undisputed queen of the juvenile division, having beat top colts in all three starts and remaining undefeated.
Regret made her 1915 by shocking the country. The “Legend of the East” would make her first start as a 3 year old in the Kentucky Derby. This guaranteed the race would get national attention, as the Derby was not a prominent race so early in the 20th century. Rowe and Notter slept in the stall next to the filly’s for a week prior to the race. Regret went off as the favorite in a 16 horse field. It would be her first race at a distance longer than 6 furlongs, and her first race of the year, but that made no difference to the fans who had followed her 2 year old career. And Regret lived up to their expectations, leading the field wire to wire to win by two lengths over Pebbles. She became the first filly to win the now prestigious race (14 others had tried before), and no other filly would match strides with her until Genuine Risk won 65 years later, in 1980. Regret won the race in 2:05 2/5. She was accredited as having made the Derby “an American institution” by Churchill Downs general manager Colonial Matt Winn.
She had come out of the Derby with a breathing defect that stayed with her the rest of her life, and some believed Regret never quite recovered from her Derby victory. The chestnut only made one more start at 3, the Saranac Handicap at Saratoga in August. After a 3 month layoff it would be another stern test for her. She was co-highweight with Belmont and Withers winner The Finn, who only conceded her the three pound sex allowance. (The Finn carried 126lbs, while Regret carried 123lbs.) Regret was up to the task, and ran in her usual wire to wire style and keeping her undefeated record intact. Even though she had only raced twice that year, she was considered by many the best horse in training for 1915, regardless of age or sex.
An entire year went by before Regret made another appearance for the 1916 Saratoga meet. Here Regret would be handed her first defeat. She started in the Saratoga Handicap and set a fast pace, but faded to last after the first half mile. Rowe then placed her in an allowance race, where she won easily and defeated Flittergold, a full brother to Fair Play. Afterwards she returned to the farm. This would be her only season where she wasn’t regarded a champion.
Regret’s 5 year old season was next to flawless. For the first time, she started in a race restricted to her own sex, an overnight allowance at Belmont Park. She won without being challenged, giving weight to all the competitors. From there she went to the Brooklyn Handicap, which marked the first meeting of Kentucky Derby winners on a racecourse. Old Rosebud was the winner of 1914, along with 1917’s victor Omar Khayyam. Regret broke sharply and led throughout the first mile and sixteenth, turning back one challenger after another. But in the final hundred yards, she was caught and beaten by a nose by her stablemate Borrow.
Controversy surrounded that race. Some believed that Willie Knapp, Borrow’s jockey, had ignored Whitney’s orders to hold him back and let Regret win. Others report that there were tears in Knapp’s eyes as he led Borrow to the winner’s circle after the race. A third group insists that Old Rosebud made a bid for the win at the same time as Borrow, and Knapp had simply been trying to hold him off and keep Regret ahead of the older horse. The truth is open for speculation but will never truly be known.
The mare’s next race was the Gazelle Handicap, her only sex-restricted stakes race. She raced under 129 lbs but had no problem defeating her rivals, which included Coaching Club American Oaks winner Wistful. Regret’s next and final race was an overnight at Aqueduct, and it was more an exhibition than a race. She carried 127 lbs and only had one opponent, Ima Frank, who carried 109 lbs. Regret won by three lengths without being pushed, and set a new track record of 1:24 1/5 for seven furlongs. She was declared the leading older female champion that year even though she only raced four times.
Regret became a legend in her own right. She raced 11 times, winning 9 and only placing off the board once. She was the first filly to conquer the boys in the Kentucky Derby, and also the first NJ-bred to win that race. She was never beaten by a member of her own sex, and was undefeated at ages 2 and 3. She was a champion of her division three out of her four racing years. In 1957, she was inducted into racing’s Hall of Fame. After all that, did Whitney still regret that she wasn’t a colt? Highly unlikely.