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Written by Presley White

Regret was one of the greats of racing. She was the first filly to win the Kentucky Derby, in a time when racing was different then it is today, a time when colts were simply considered “better” than fillies. It was a time when some of the greats of racing (ex. Man O’ War and Exterminator) were beginning or ending their brilliant careers. From undesired to being a vital part of thoroughbred history, Regret was part of it all.

Regret was by the amazing stallion Broomstick. A nice stakes racer in his own right winning the Travers Stakes, Broomstick would become one of the nicest sires of all time. He stallion record said it all: he was the leading sire in 1912-1915, was on the top ten sires list from 1910 to 1927, and an amazing 25% of his foals would turn out to win some sort of stakes race. Broomstick was crossed with a very nice and hopeful broodmare named Jersey Lightning. Although Jersey Lightning was an untried mare she looked the part. The Harry Payne Whitney Farm was very anxious about the upcoming colt. But when the spring of 1912 came around they discovered that the foal was a filly. They named her Regret, as in they Regretted that she was a filly not a colt. Soon enough their thoughts would be changed.

When regret was a yearling she was sent to trainer Jim Rowe. He thought that there was something special about her. He tried to bring her along slowly and give her time. Rowe thought of Regret as the best of the Whitney yearlings and had high hopes for the Saratoga meet in 1914.

Even in her first race Regret was tested. She did not start in a maiden race or an allowance race. Rowe put her in the Saratoga Special, a two year old stakes. She also had to compete against colts in this race and one of the colts was the season’s top two year- old colt, Pebbles. She came in as co-favorite because of her workout times that were said to leave smoke on the track. She most certainly did not disappoint as she won the race by a length over Pebbles and the rest of the field. She was untouched throughout the race showing the front running style that almost all of the Kentucky Derby winning fillies since, have used. The victory quickly put Regret on the map.

Although the rest of her two year-old-season was short it was none-the-less brilliant. A few days after her romp in the Saratoga Special, Rowe entered her in the Sanford Memorial. In this race she would have to carry 127 pounds. The weight did not seem to bother her as he moseyed across the wire in front. Then came the Hopeful Stakes. It had rained all the night before and the track was running very sloppy. Regret did not disappoint as she strode home like the lady she was without getting any mud even on her blazed face. She was undisputed by the best of the crop. She won three stakes in only fourteen days and her trainer decided to give her a rest so that she would be ready for the upcoming three-year-old season.

The whole world was shocked when the first start of the unseasoned filly was the Kentucky Derby! No filly had been able to conquer the race in its history. Twelve had tried, but all had failed miserably. Only one female before Regret had been able to place in the race, Lady Navarre was a brilliant long shot and that was about all. Regret had been able to defeat the best of her crop the previous year, but could a filly possibly win the esteemed race?

The 1915 derby shaped up to be a very competitive race. During the years previously, the famed Kentucky Derby, Churchill Downs had suffered a major economic blow. The derby of 1915 would cause the derby to become one of the biggest races and put Churchill back on the map.

The blazed faced filly was in peak condition for the race. She had obviously been trained very well. The filly had also been trained in an unusual way for us in the modern world. She had run two brilliant workouts at the full length of the looming Kentucky Derby! Pebbles the rival of Regret was also at the race. Regret had defeated him before in one of her few juvenile starts, but could she do it again? The derby was also different back then in the fact that all horses carried different weights much like in a handicap race.

Regret carried 112 pounds, this was 15 pounds less than what she had carried in her last race against Pebbles. While no filly before Regret had won the classic, there was female participation precedence, a shortened distance, and Regret's juvenile experience running against colts. There seemed to be a reason that she was the 5-2 favorite. She may have been even money if not for the rumor that she had not traveled to Kentucky well. People even went so far to say that she was off of her game. She made all of these people shut their mouths rather quickly.

The filly put all doubts to rest and showed that she deserved to be the favorite when she won wire to wire. Pebbles came late but had no chance of catching the amazing filly as she streaked in front of the finish line becoming the first filly to ever win the Kentucky Derby. She would only race once more as a three year old. In this race she would overcome the famed winner of the Belmont Stakes. That victory along with the derby win were enough for her to earn the award as the Horse Of The Year

As a four year old she would repeat her former season with only two starts. One of these races was against the great Fair Play’s full brother, but she would defeat him easily. But in her other start as a four year old she would taste defeat for the first time in the Saratoga Handicap. The horse that would beat her by a nose, Burrow, her stable mate, would set a record for the race.

As a five year old the filly was brought back in the Gazelle Handicap in which she was triumphant. She would race only one more time in her career. It was an overnight handicap and only one horse dared to race Regret. Even though she was being held up, Regret set the new track record and most certainly went out with a bang.

Regret was retired to be a broodmare at the Whitney Farm. As a broodmare she produced stakes winner Revenge, and stakes placed Penitent before her death in 1934. She was laid to rest at the age of 22 at the Whitney farm in Lexington, her forever home. In 1957 she was inducted into the Hall Of Fame. She was on the list of the top one hundred horses in the twentieth century.

She was truly what her name implied, for everyone that ran against her, regretted it. Regret was the first filly to win the Kentucky Derby and it would be another sixty-five years before another filly would have a blanket of roses placed over her back. For those who look deeper though, she was not only a derby winner but a magnificent horse for the ages. As long as horse racing is continuing she will be remembered for more than a record. She will be remembered more than her earnings on a sheet of paper. She will be remembered for the legacy that she left behind. The legacy of a filly tough enough to beat the boys, and although Winning Colors and Genuine Risk have now joined her as filly Derby winners, the first will never be forgotten.

Regret Facts:
Owner: Harry Payne Whitney
Trainer: James G. Rowe, Sr.
Racing silks: Light Blue, white sash, brown cap.
Sire: Broomstick
Dam: Jersey Lightning
Color: Chestnut
Race Record: 11: 9-1-1
Earnings $35,093

Special Notes:
- Not since 1915 has more than one Triple Crown race been won by a filly.
- Throughout her career, she was never beaten by a female horse.