Winn’s Regret

When she was born in New Jersey on the Whitney Farm, no one had any idea how Regret would help Matt Winn make the Kentucky Derby what it is today. It is impossible to talk about this amazing filly without talking about Winn, because their legacies are forever entwined.

Fillies often stand in the shadow of colts and stallions as to their abilities and worth. However, 2016 demands a different look, because it is the Year of the Filly/Mare with horses like Beholder, Songbird, Tepin, Lady Eli and Stellar Wind. While the Queen Beholder retires, one can’t help but think of another Queen who raced brilliantly into history over a hundred years ago as events and dreams swirled around her. 

When she was born in New Jersey on the Whitney Farm, no one had any idea how Regret would help Matt Winn make the Kentucky Derby what it is today. It is impossible to talk about this amazing filly without talking about Winn, because their legacies are forever entwined. 

It all began with Colonel Meriwether Clark, Jr., aka Lutie, when he traveled to Europe in 1873 visiting prestigious racetracks. Horse racing changed dramatically in that they no longer ran heat races, which they still did in the U.S. Heat races are when horses run 3 four mile races in one day to determine the winner. In England, they ran shorter races, and horses were only raced once on a certain day. He also discovered pari-mutuel betting in Paris, which unbeknownst to him, would help save the Kentucky Derby, Churchill Downs, and horse racing many years later. 

When he returned to Kentucky, he built a track outside of Louisville and based races upon the European versions he saw. He created three races for opening day which were the Clark Handicap based upon the St. Leger, Kentucky Oaks based upon the Epsom Oaks, and the Kentucky Derby based upon the Epsom Derby. 

Matt Winn, who was 13 years old in 1875, went with his father to the inaugural races. His father hitched their horse to the wagon, and they rode through the biggest traffic jam in Louisville ever saw to the infield of the track. 

“It was a thrill for me, the first Derby, with crowds swirling around in the infield, the grandstand a riot of color, and tenseness in some places, unrestrained enthusiasm elsewhere, as the time neared for the horses to parade to the starting line….,” commented Matt Winn. When Aristides won the race, beating the favorite Chesapeake, the bug bit. Winn was hooked, and he went to every single Kentucky Derby until his death. 

Lutie had a great dream, but creating a profit eluded him. When he built the track, he put the grandstand on the opposite side of where the stands are now, so the sun blinded racing fans. He built a house on the grounds and entertained those that came to the track turning the race meets into a very successful social scene, which is where he flourished. However, he was known for being touchy, and his ill temper resulted in him pulling a gun on those he disagreed with more than once. 

Troubles began for the track when James. B. Haggin, brought his horse Ben Ali to race in the 1886 Derby from New York. Bookmakers were not allowed to take bets Derby day due to a problem with the bid-and-asked for license fee. This upset Haggin, and he stated that if the problem wasn’t resolved, he would ship all of his horses back to New York. When officials heard these comments, one of the officials wondered aloud who Haggin thought he was, and if he wasn’t happy, he should ship them all back. 

Ben Ali won the race, and during the celebration, someone told Haggin what the official said. He exploded and the next morning all of his horses were gone. Very well known in New York, he spread the news about his treatment, which caused east coasters to boycott the Kentucky Derby for more than 25 years. Only Mike Dwyer brought a horse from the east in 1896. This lack of participation by high class three-year-old horses, turned the Kentucky Derby into more of a local novelty. 

Churchill Downs, as it became known, never made a profit, and eventually, the operators of the track voted to close it unless they found a buyer. In 1902, Charlie Price, who represented the owners that bought the track in 1894 and built the new grandstand with the twin spires, approached Winn about buying the track for $40,000. After trying to get out of it, Winn gathered some friends together, and they decided to buy it. Winn couldn’t let his beloved Kentucky Derby die. 

Before Regret was even a thought, Winn began working his magic. First, he created a Jockey Club, and with the funds raised from membership, he built a new clubhouse. When they opened for its Spring meeting in 1903, the track made its first profit. In 1904 Winn became General Manager of Churchill Downs, and his public relation skills were put into play. He always followed advice from his landlord. Winn once asked him how to be a successful businessman, and his landlord replied, “I can give you the answer in just three words—always be polite.” 

With his polite and jovial personality and a cigar, he took on several battles. His first task was to obtain better racing dates and more days, however the Western Turf Association refused to give any dates. Winn responded by forming the American Turf Association with nine other tracks in opposition to the WTA, and after two “bitter” years, Winn and his group surpassed the WTA with bigger purses and crowds. WTA conceded to the terms of the ATA, and the Turf War came to an end. 

In 1908 a reform movement spread through the United States aimed at shutting down bookmakers. Laws passed in several states closing several racetracks including Belmont Park from 1911-1912. The reform movement moved into Kentucky after a nasty political battle for office. 

The political group that came into office in January 1908 decided to exact revenge upon Charles Grainger, President of Churchill Downs, who avidly lobbied against them. They decided to shut Churchill down and end the Kentucky Derby by declaring bookmaking illegal, which the anti-Grainger County Sheriff promised to enforce with gusto. After extensive searching, the Churchill board discovered an amendment to the law prohibiting bookmaking stating that pari-mutuel betting and auction pools were allowed. When Lutie tried to use the pari-mutuel machines, he must have had this amendment added to the law prohibiting bookmaking. Even though Meriweather had the machines in 1875, he didn’t use them until 1878. 

A furious search by the community and friends began for any and all pari-mutuel machines. They found one in the storeroom of the racetrack, one at a pawn shop, another found in pieces, two were shipped from New York and a souvenir hunter brought in another. All were in a state of disrepair, but luckily mechanics were able to fix them. 

Despite having the law on their side, the government threatened to arrest anyone involved with any aspect of gambling in auction pools or the pari-mutuel machines. The Churchill board requested an injunction preventing action by government officials until the Court of Appeals could rule on the validity of the amendment. The injunction was granted, and the Kentucky Derby continued. 

Winn believed bookmaking would be legal the following year, and they could once again put the machines into storage. However, anti-bookmaking laws stayed, and pari-mutuel machines grew in popularity. Soon other tracks facing the reformist laws began installing the machines keeping or reopening tracks across the United States. 

Winn’s next challenge was to convince the owners of high quality Eastern horses to come to the Derby. He had some help from a couple of Kentucky bred horses. 

In 1911, Churchill reduced the cost of pari-mutuel betting from $5 a bet to $2 making it easier for everyone to take part. The Daily Racing Form commented on pari-mutuel betting Derby Day in 1913 writing, “Down in the pari-mutuel department under the broad and long shed, which covers nearly an acre of historic ground, a great mass of men swirled and turned in a constant effort to make their way to and from the machines and the cashiers.” 

On May 10th, 1913, a Kentucky bred horse named Donerail stepped onto the track at 91-1 odds, and he beat the favorite with ease setting a new Derby and track record of 2:04 4/5. A two-dollar bet reaped huge rewards for his few followers. Winn told Frank Menke in their book Down the Stretch, “The story about Donerail, which in some of the far away papers might have been good for only a paragraph, was built into one that warranted headlines. The functions of the pari-mutuel machines, not very well known outside of Kentucky and Maryland, and the fact that $2 invested in Donerail’s ability would have rewarded with a net profit of $182.90 was something for the folks to talk about for many weeks.” 

Donerail helped Winn get the Derby into the national spotlight, but more was needed. Another Kentucky bred horse caught the public eye. 

Old Rosebud touched the track with his beautiful hooves and won the Derby by eight lengths setting a new track and Derby record of 2:03 2/5. The DRF wrote, “It was Old Rosebud first and the rest of the seven starters nowhere.” His time would stand for sixteen years, and three other horses have tied the 8-length victory in the Derby, but no other horse has broken it. 

The New York Times noted more than just Kentuckians attended the Derby in 1913, “The running of the Derby…., was witnessed by one of the largest crowds that ever attended the event, including many society folk from neighboring cities, and leaders in turf circles from all over the country.” 

The road to the Derby begins outside of Kentucky. Horses and their people find their way to Saratoga each summer where strawberries and cream is served under beautiful, green trees and lures avid followers from all over. Harry Payne Whitney and James Rowe brought a horse they knew was special. A beautiful chestnut filly with a strong white blaze painting her face.  Sired by Broomstick and out of the dam Jersey Lightning, she prepared to make her debut. They were so confident in her abilities they put her up against the boys in her first race; the Saratoga Special. 

Even though she led the race from start to finish winning by a length, most chalked it up to luck. Pebbles, the star two-year-old colt, could not be beaten by a filly, so it had to be a fluke. “…hers was a lucky score, for had not James Butler’s Pebbles been practically left at the post he surely would have been returned the winner.” Surely the next time they met, Pebbles would dominate. 

A week later she went up against boys in the Sanford Memorial at Saratoga. She was an added starter making the other entries a bit nervous considering her domination in the Special a week ago. Like the Special, she maintained the lead from start to finish never being tested. This is when “queen” was first applied to her. “In the running Regret was the same queenly lady that she was in the Saratoga Special,” wrote the New York Times

The rematch between Regret and Pebbles came on August 22nd in the Hopeful at Saratoga. Regret carried 127 pounds on a heavy track from recent rains. This time she couldn’t go to the front, dropping back to sixth place. Everyone maintained their positions throughout the race until the stretch when Trojan moved to the lead. Joe Notter, Regret’s jockey, maneuvered Regret to the outside away from the heaviest part of the track, and with each driving stride she wore Trojan down seemingly breaking away from the others only to be caught by Andrew M. Ridden hard to the end she won by a head. Andrew M carried 114 pounds, while Pebbles carried 113 into third place. There was no doubt after this race that Regret was anything but a fluke. Three times she beat the boys easily and hard fought in two weeks. Whitney and Rowe let her rest after this race for 259 days. 

Regret caught Winn’s eye, and he knew she needed to be in the 1914 Kentucky Derby to entice top east coast racehorses back to the Derby. Through contacts made at Empire City, another track in New York that Winn opened and managed, he put the invitation to Whitney. He dangled a winner’s purse of $11,450 and a gold cup, which was far more than any track on the east coast paid out for prestigious races such as the Belmont and Preakness Stakes. Whitney agreed, and Winn got high quality horses from New York blue bloods back into the Derby. 

Many believed they raced the Derby too early in the year for three-year-olds, especially since there were no prep races due to winter. Weather didn’t stop Rowe or Whitney from training Regret for the Derby. A storm blew six to eight foot drifts onto Whitney’s training track, so Whitney hired everyone he could to shovel it away to continue Regret’s training. 

No one is sure why she didn’t race for 259 days. Was she hurt, or were they just giving her time to rest and grow into a more mature horse? What is certain is when she shipped to Kentucky, she didn’t fare well. She went off her feed, and her works were lackluster. Some say she was in heat, but others seem to think something else occurred. It is possible she suffered from a shipping illness similar to Beholder. 

Notter explained, “Trainer Rowe and I slept in the stables all week. I won’t forget that experience. 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 2:14⅗, and then three days before the race repeated her work going the distance in 2:08⅗. Mr. Rowe wondered if he should run Regret…. I told him not to worry. The mare will be alright. We will be in front before the others can get on stride,” 

When Rowe decided to race her, another situation arose. The Lusitania was attacked by a German U-boat on May 7, 1915 a year after World War I began. The British ocean liner sailed from New York to England, and one of the passengers on the ship was Alfred Vanderbilt who happened to be the brother-in-law of Whitney. After giving his life vest to another woman despite not being able to swim, Vanderbilt stood on the deck with friends as the ship sank. 

Whitney, out of respect for his wife’s family, nearly pulled Regret out of the race, but Vanderbilt’s fate was unknown. Everyone held hope he might be alive, so Whitney kept Regret in the Derby. 

When the gates opened, people filled the stands. “It was a gay crowd of well-attired people who made a veritable picnic of their outing under sunny skies,” wrote the DRF. Despite raining for several days prior to the Derby, the track dried out. 

Little String was the first of sixteen entries to appear on the track for his warm up canter. The additional fifteen appeared one by one for their sprints before returning to the paddock. After watching the horses in the paddock and canter in front of the stands, thousands of people made their way to the pari-mutuels to place their bets. The horses headed to the post, and after a four-minute delay, they were off. 

Regret went immediately to the front of the pack and never relinquished her lead. Her rival Pebbles followed her the entire way never finding that gear to overtake her; no one could. “It turned out to be one of the easiest victories of my entire riding career. It was so easy in fact, that I can’t count it among my greatest racing thrills,” stated Notter after he retired. 

“When Regret 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 has done something that no other filly had accomplished,” wrote T.B. Cromwell for the DRF

“Someone said before the race, ‘It’s Jimmy Rowe that makes this filly the favorite.’ It was partially true, but not in the sense that he meant it. Rowe, wonderfully cleaver trainer that he is, could not have made Regret win had she not possessed the qualities of a winner such as she proved herself to be. Neither could the marvelous skill of Joe Notter as a rider have brought her to the winning post in front had she not been swift and game with an abundance of stamina,” wrote Cromwell. 

When Whitney greeted his filly, he looked upon her with a face painted with awe and sadness. Awe for his horse, and sadness for the Lusitania tragedy. He smiled at her and said, “I do not care if she never wins another race, nor if she never starts in another race, she has won the greatest race in America and I am satisfied,” wrote Cromwell. 

“The triumph of Regret, a filly and a Whitney filly as well, was perfect. It fired imaginations everywhere,” wrote Arthur Daley years later. 

The top three finishers in the 1915 Kentucky Derby were from New York putting the Derby back on the map as a high-quality race. Even with the sinking of the Lusitania, Regret’s win appeared in papers around the country. Winn had his win, but he never rested on his laurels. 

Winn wrote in his book, “It needed only a victory by Regret to create for us some coast-to-coast publicity, and Regret did not fail us. The Derby thus was ‘made’ as an American institution…” 

Even though Winn managed other tracks, Churchill Downs and the Kentucky Derby were his loves. He tirelessly worked to promote the race and the track for the rest of his life. William H.P. Robertson, in “The History of Thoroughbred Racing in America,” called Winn “a Moses who led the sport through trying times.” Regret and Winn turned it the Derby into the American Classic race it is today. They couldn’t do it without one another. 

Because of Winn’s constant work, fight, and promotion, the Kentucky Derby is the longest running race in the United States. When the U.S. government wanted to shut the Derby down during World War II, instead of fighting, he asked the government how he could satisfy their concerns. The Derby became known as the Streetcar Derby, because everyone took public transportation to attend. Due to his resolve to keep the race going that year, Count Fleet became the sixth Triple Crown winner that year. 

Whitney entered horses in every single Kentucky Derby after Regret’s win without luck until 1927 when he won with Whiskery. After the race, there was a big party, which Whitney’s son, Sonny, became bored with. He wandered outside and heard singing down by the stables. He walked over and found grooms and stable hands singing spirituals to a horse standing in silhouette by a bonfire. When asked what was going on, he was told, “Why, Mister Sonny, that’s Regret. She was the first one ever carried home the blue in the Derby race, and we been waiting twelve years now to have another celebration.” Sonny Whitney elaborated, “I always think of racing in terms of that singing, that bonfire, and that dark mare against the flames.” 

The Louisville Courier Journal wrote, “… never shall we forget her gorgeous appearance on that memorable afternoon in May at Churchill Downs as she was led around the paddock before the race and later, when, with colors up, she stepped out on the course looking every inch a queen … receiving an ovation of which even royalty might well have been proud. Peerless Regret she was hailed and peerless she undoubtedly was, and from this day, she must be thought of with this descriptive adjective affixed.” 

Author: reenchantedOTTBS

I'm an artist, writer, and a lover of thoroughbreds. I was born and raised in horse racing, and now I wish to help rehome them, educate people about how fantastic they are, and show what they can do.

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