According to Matt Winn, she made the Derby “an American institution” (Hotaling).

According to a New York Times writer in 1914, her entry in the Sanford “caused something of a panic among the others who had starters” (“Whitney Horses”).

She made only 11 lifetime starts, but the mark that she left on racing is indelible, and her name is about the only thing about her that doesn’t make sense.

Harry Payne Whitney’s Regret made her first start in the Saratoga Special, racing against colts. After her win with a three pound weight concession, the racing secretary at the Spa assigned her 127 for the Sanford. No problem: she beat the colts there, too. And conceding thirteen pounds to the second place finisher, she won the Hopeful not long thereafter.

And there you have Regret’s two-year-old campaign: three starts, three wins. All stakes, all against colts, within fourteen days, at Saratoga. In the Special and the Hopeful, she beat Pebbles, the colt who would go on to be known as two-year-old champion.

These three victories earned Regret a ten-month vacation from racing, and Whitney chose the Kentucky Derby for her three-year-old début. Her start in that race was briefly in doubt, as Whitney’s brother-in-law, Alfred Gwynne Vanderbilt I, died when the Lusitania went down the day before the race. Whitney decided to honor his commitment to the Derby, but raced no more that year.

Regret won the Derby by two lengths, “easing up”; Pebbles was second to her again. Leased to L.S. Thompson during Whitney’s mourning period, Regret raced only once more at three, back at Saratoga in the Saranac. She won that by a length and a half, beating Travers winner Lady Rotha and Belmont winner The Finn, the horse that the New York Times considered 1915’s horse of the year.

In her only start at four, Regret finished last in the Saratoga Handicap.

Back on the track at five, Regret made the first start of her career in a sex-restricted race, an allowance at Saratoga; following a very close second (due to an “overconfident ride,” according to Champions) in the Suburban, she raced for the first and only time in a sex-restricted stakes race, the 1917 Gazelle at Aqueduct. She carried 129 pounds and won by three with “speed in reserve.”

Regret made one more start that year—another win—and was retired with a race record of 11 – 9 – 1. She never finished behind another filly or mare. In a time when horses not uncommonly made dozens of starts, Regret was undeniably lightly raced…but it’s not as if Whitney coddled her: she made the first start of her life in a stakes race against colts, and she won the Derby off a layoff of nearly a year. One could argue that he simply took care of his prized filly.

Regret was a decent if unremarkable broodmare, though her offspring might be known more for the cleverness of their names than for their performance on the racetrack: Penitent; Revenge; Nemesis; Stigma; Repenter; Mea Culpa; Rueful.

During Regret’s career, Horse of the Year honors were not determined by voting. According to Women of the Year: Ten Fillies Who Achieved Horse Racing’s Highest Honor, “[o]fficially recognized voting” for champions didn’t begin until 1936. During the writing of a book called The Great Ones, published by The Blood-Horse, then-editor of that publication Kent Hollingsworth “waded his way through sundry historical accounts to determine a legitimate, although unofficial, list of champions dating back a century to 1870.”

And according to Hollingsworth, Regret was 1915’s Horse of the Year, even though she raced only twice. His designation is hardly definite, and one would likely find plenty of dissenters, given Regret’s extraordinarily light campaign. What is certain is that the title hardly matters, not to those who saw Regret race, and not to those who recall her achievements. Of her Derby victory the Daily Racing Form reported:

As the winner jogged back to the stand the crowd broke forth in another great
roar of applause, for they recognized in the filly a marvel of her breed and
sex. She had done something that no other filly had accomplished.

Nor did such a title seem to matter much to at least one of her connections. Harry Payne Whitney won a second Kentucky Derby with Whiskery in 1927, and in her chapter on Regret, Avalyn Hunter relates the following anecdote:

That night Sonny Whitney became bored with the post-race celebration of the rich
and famous in his father’s house and wandered outside. There, in a field not too
far from the stable, he found the stable hands gathered about a bonfire, holding
a party of their own and singing spirituals. And the guest of honor? Regret, who
had been brought over from her quiet broodmare paddock so that she might share
in the festivities. It was a defining moment for young Whitney, who would later
recall the sound of spontaneous joy and the sight of Regret silhouetted against
the flames as one of his most cherished racing memories.

For more on the fillies and mares who were designated or voted Horse of the Year, check out Valerie Grash’s series at Fillies First.

Works cited and consulted. The New York Times article are free.

Champions. New York: Daily Racing Form Press, 2000.

“Gazelle Handicap Easy for Regret.” New York Times. 11 July 1917. Web. 28 Nov. 2009.

Hotaling, Edward. They’re Off! Horse Racing at Saratoga. Syracuse: Syracuse University Press, 1995.

Hunter, Avalyn. “Regret.” Women of the Year: Ten Fillies Who Achieved Horse Racing’s Highest Honor. Ed. Jacqueline Duke. Lexington, Kentucky: Eclipse Press, 2004. Print. 61 – 76.

“Interest in Horse Racing Revived.” New York Times. 12 Dec. 1915. Web. 28 Nov. 2009.

“Regret Captures Hopeful Stakes.” New York Times. 23 Aug 1914. Web. 28 Nov. 2009.

“Regret from End to End.” Daily Racing Form. Kentuckiana Digital Library. 9 May 1915. Web. 28 Nov. 2009.

“Whitney Horses Take Two Stakes.” New York Times. 16 Aug 1914. Web. 28 Nov. 2009.