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Regret: First to Beat the Boys in Kentucky Derby
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He rarely took no for an answer.
An enterprising young tailor in Louisville, Martin J. “Matt” Winn saw an opportunity where others saw problems. In 1902 the Churchill Downs racing facility was in serious financial trouble and in danger of closing. Winn assembled a group of local investors, bought the track, and the right to the name the Kentucky Derby. Later he changed the wagering from bookmakers to a paramutuel betting system. In 1911 he changed racing forever, by introducing the two dollar minimum bet: in the past, the minimum pari-mutuel bet had been five dollars, beyond the reach of most working people.
The racing impresario's greatest coup may have been when he is credited with persuading Manhattan mogul owner Harry Payne Whitney to enter his filly Regret in the 1915 Run for the Roses. The muscular chestnut led wire to wire and came home a two length winner. Regret became the first filly to triumph in the Derby. As Winn had envisioned, Regret's victory brought an avalanche of newspaper coverage to Churchill Downs' signature race. Her victory against the boys was a turning point in elevating the race’s popularity nationwide, and since then the Kentucky Derby has enjoyed a prestige equal to any global sporting event.
Years later Winn reflected on that day: "The race needed only a victory by Regret to create some more coast-to-coast publicity to really put it over. She did not fail us. Regret made the Kentucky Derby an American institution."
Near the small town of Red Bank, not from the coast of New Jersey, a foal was born at Harry Payne Whitney's Brookdale Farm in the spring of 1912. By the mighty stallion Broomstick out of the great mare Jersey Lightning, she was a pretty filly with a white, wide blaze. Still, Payne was slightly disappointed since he had hoped for a colt. He named her Regret, an impulsive misnomer if there ever was one.
The son of New York city financier William C. Whitney, "Payne," as he was known, in 1896 married Gertrude Vanderbilt, the eldest daughter of Cornelius Vanderbilt, uniting two families of great wealth and prestige. He received a substantial inheritance from his father as well as his uncle Col. Oliver Hazard Payne. Whitney had major holdings in banking, tobacco, railroads, mining, oil and a powerful stable of thoroughbreds among his array of investments.
Whitney had been named leading American owner on eight occasions, and throughout his life was the breeder of almost two hundred stakes winners. His trainer, the legendary Jim Rowe, conditioned 1908 Horse of the Year Colin. Regret broke her maiden at first asking in the 1914 Saratoga Special. She defeated the top colt Pebbles, who would become an arch rival, winning by a length with "speed in reserve" according to the Daily Racing Form.
The racing secretary assigned Regret an impost of 127 pounds when she returned to the historic Saratoga racetrack a week later for the Sanford Memorial . No problem. Under jockey Joe Notter's tight hold, Regret outran a field of eleven colts to claim victory by a length and a half. Seven days later she was back at it, churning through heavy mud at Saratoga to win the Hopeful Stakes while spotting thirteen pounds to the runner-up.
Regret became the first horse-- colt or filly-- to sweep the trio of signature Saratoga races for juveniles. Only three others-- Campfire (1916), Dehere (1993) and City Zip (2000)--have accomplished that feat.
Having earned $17, 390 in a span of fourteen days, Whitney sent the prized filly back to his northern Jersey farm. For her dominant season, Regret was rewarded with the title of Champion Two Year-Old Filly. Her three year-old campaign kicked off in the 41st Kentucky Derby, though Rowe was not completely sold on the idea. The filly had not raced in 259 days.
“Trainer Rowe and I slept in the track stable all week, I won’t ever forget that experience," said Notter years later. "The roof leaked and when it rained during the six days we spent there I got soaked. Regret went off her feed down in Louisville. She worked well enough in New Jersey, but the train ride upset her. At Churchill Downs, she worked the Derby distance first in 2:14?, and then three days before the race repeated her work going the distance in 2:08?. Mr. Rowe wondered if he should run her.”
Colonel Winn eventually convinced Rowe to start the regal, unbeaten chestnut filly. She attracted overflow crowds in a pair of public breezes comparable to the full length of the mile and a quarter Derby.
With a reported crowd of 49,000, Regret went off as the 5-2 favorite in the field of 16-- the lone filly. When the flag dropped she shot like a bullet to snatch the lead. Pebbles, her chief juvenile rival, sat just off the pace and tracked Regret throughout. With Notter in the irons, Regret easily turned back Pebbles' late charge and drew clear by two lengths in the historic victory. The gorgeous filly shaved two seconds off Old Rosebud's track and stakes record, winning in 2:05 2/5. Rowe celebrated his second score in the Derby. Rowe's previous victory was with Hindoo in 1881, thirty-four years earlier. Prior to Regret, a reported 29 fillies had competed in the Derby without a victory.
“Isn’t she the prettiest filly you ever saw? You know, this is the greatest race in America at the present time and I don’t care if she ever starts again,” said Whitney after the race. “The glory of winning this event is big enough. Regret can retire to the New Jersey farm any time now.”
Regret did race on, returning to Saratoga in August for the Saranac Stakes where she battled Finn, the winner of the Belmont, Withers and Manhattan Handicap. She was never challenged, winning in a hand ride by one and a half lengths. Regret was named Horse of the Year.
The filly experienced defeat for the first time at age four, and then again at five, though the latter marked one of her most superlative efforts. The 1917 Brooklyn Handicap produced, arguably, one of the greatest fields ever assembled on an American racetrack at one time. The lineup included three Kentucky Derby winners-- Regret, Old Rosebud and Omar Khayyam-- future Hall of Fame inductee Roamer, future leading sire Chicle, and handicap stars Borrow, Stromboli and Boots.
Regret claimed the lead immediately, holding off challenge after challenge throughout the first mile and a sixteenth. Then Borrow came roaring down in the final strides to edge the filly by a desperate nose, setting a new American record of 1:49 2/5 for a mile and an eighth. Regret had spotted the victor five pounds.
Regret's final competition was a handicap race on September 25, 1917 at Aqueduct, which drew just one rival. She touted 127 pounds while her only challenger carried a mere 109. Despite a snug hold by Notter, Regret set a seven furlong track record of 1:24 1/5 for the seven furlongs, winning by three lengths.
Regret was retired in 1917 with a slate of nine victories and one place in eleven starts, earning $35,093. Expectations were enormous for Regret as a broodmare. Unfortunately, she did not match her prowess on the track. Only one of her ten foals, Revenge, was a stakes winner, while Penitent was stakes placed. Regret died at age 22, on April 14, 1934. Her grave sits on a tranquil hillside of the Whitney farm, today known as Gainesway Farm near Lexington, Ky.
Regret's legacy shines brilliantly through the annals of American racing. It was sixty-five years before another filly, Genuine Risk, won the Roses in 1980. Winning Colors entered that exclusive club in 1988. Regret was inducted into the Racing Hall of Fame in 1957.
Writer & Historian
Terry Conway has been a regular contributor to The Blood-Horse magazine since 2003. He started writing historical racing articles for ESPN.com in 2010 and the Jockey Club’s America’s Best Racing in 2012. His work has been featured on premier racing sites including the Paulick Report and Equidaily.com. He is also a member of the Turf Writers of America.
One of the most familiar sounds at a racetrack is the bugle call, universally known as the call to the post. The catchy melody is performed as the jockeys parade their horses to the track. It also alerts spectators that another race is forthcoming. Prior to the advent of the starting gates, the call to the post would signal horses to circle around and line up at a starting line and were off and running at the signal of the starter's flag.
The origin of the call to the post goes back to military traditions. Buglers and their horns were a key part of the art of warfare sending signals over a chaotic battlefield and on board warships. "First call" reveries signal the start of a new day, while Taps is the haunting strain sounded nightly by the U.S. military to indicate "lights out." Sometimes known as "Butterfield's Lullaby," it is also played during flag ceremonies and funerals, generally on a bugle or trumpet.
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