04/20/2015 3:01PM

Regret's Derby at 100: Filly made a case for equality


“You’re the top! You’re the Tower of Babel. You’re the top! You’re the Whitney stable …” - Cole Porter

Photos tell stories. This one, in muted gray, depicts two men flanking a dark Thoroughbred with an irregular splash of white sliding down her sweat-streaked face, eye rolling wildly in an afterburn of fatigued nerves. The figure on the left gazes off into space, a shadow of a smile playing across his lips. The other stares intently at the horse, his horse, who has just accomplished what many thought impossible. Stripped of saddle and winner’s floral wreath, the filly jigs impatiently as her owner looks on, surely savoring the sweet aftermath of history made. In stylish pinstriped suit and Homburg hat, the nattily dressed fellow grips a rein tightly in his right hand, cigarette dangling from the left – but appears strangely somber. It seems Harry Payne Whitney had more on his mind 100 years ago than winning a horse race – even if it was the Kentucky Derby.


A confluence of events leading up to May 8, 1915, made Regret’s victory that afternoon at Churchill Downs bittersweet. Barely 24 hours earlier, a Cunard ocean liner outbound from New York with 1,959 people aboard had been torpedoed and sunk by a German U-boat just off the southern Irish coast.

One of the 188 American names inscribed on the Lusitania’s manifest that day was Harry Payne Whitney’s brother-in-law Alfred Gwynne Vanderbilt, who was en route to a meeting of the International Horse Breeders’ Association in London. Vanderbilt, a wealthy sportsman and philanthropist, would prove a gentleman of highest order to the final instant of his life. Within moments of a torpedo slamming the ship’s starboard bow after lunchtime on May 7, Vanderbilt, who could not swim, hastened to aid women and children onto waiting lifeboats and was witnessed calmly strapping his own life belt onto a frantic young mother, with the reassuring words: “There … this is for your smile.” Seconds later, a towering wave swept the 37-year-old millionaire off Lusitania’s B Deck into the depths of the Celtic Sea.

When the official Derby photo was snapped, Whitney knew nothing of Vanderbilt’s fate, only that he remained among the missing. It must have been hard to celebrate, but he put on a brave face.

“Isn’t she the prettiest filly you ever saw?” Whitney queried gathered journalists, photographers – and a new breed: filmmakers – as machines clicked and whirred around him. “I don’t care if she never wins another race, nor starts in another. She has won the greatest race in America and I am satisfied.”

He had to be, at least for 1915. Out of deference to his soon-to-be officially designated “late” brother-in-law, Whitney would days later retire his famed Eton blue colors for the season.

In the broader scheme, as society grieved the loss of one of its own and racing celebrated the crowning of a queen, America stood at a critical crossroads – between war and peace, freedom and oppression. Though not yet involved in the conflagration sweeping Europe, the Lusitania affair warned that the nation might not long remain neutral. And for women, a battle on the home front burned just as hot.

Blue bloods

Regret was only the 15th of her sex to attempt Louisville’s rapidly evolving classic. As indefatigable as a diehard suffragette and hell-bent to win, she was clearly the best Thoroughbred of her age in America, male or female. A Derby victory would serve as symbolic inspiration to a rising generation of girls looking for such, wherever they could find it.

The progressive era of reform ushered in by President Teddy Roosevelt was in its waning days in 1915, but for women, change had come slowly. Most upper- and middle-income females stayed home, while women from the lower classes endured long hours, low pay, and miserable conditions in the few jobs available to them. College educations remained relatively rare, and divorce rarer still, no matter how miserable the marriage – situations largely unchangeable for women as they only had the right to vote in a few western states.

No law, however, was needed to liberate Regret, who stood at the apex of her sport from birth. There were no “Cinderellas” in the Whitney barn, or in the Whitney household. All were bred and raised for presumed greatness. The daughter of Hall of Fame champion and leading sire Broomstick, Regret hailed from a power-packed female line rimmed royal blue back to before the Revolution. Her third dam, Modesty, had famously stomped male foes in the inaugural American Derby of 1884, then the country’s premier race for 3-year-olds. It got no better than that.

Harry Payne Whitney was the eldest son of cold-blooded capitalist William Collins Whitney, a leading libertarian of his day (then called a “Bourbon Democrat”). W.C. Whitney, who served as Grover Cleveland’s secretary of the Navy, supported big business with minimal restrictions and opposed overseas military intervention. The brooding but brilliant Wall Street lawyer possessed the gifts of a natural leader, and twice during the 1890s was considered a possible Democratic contender for the presidency. Business – and a growing fascination with horse racing – ultimately prevented him from going that route. (Whitney bred at least 26 stakes winners in just a few short years of racing involvement, including the future Hall of Fame champion filly Artful.)

Harry’s mother, Flora Payne, was no slouch herself. The highly educated daughter of a two-time presidential candidate (Sen. Henry Payne of Ohio), she was gifted as a writer, an accomplished musician, a noted philanthropist, and a vivacious society leader. Flora was her husband’s match in every way before her untimely death to heart disease at 51. In her 1893 obituary, the New York Times described her as having possessed “the most commanding of minds,” and that “she conferred on terms of equal knowledge and sympathy” with men of genius.

The product of this formidable duo was born into Park Avenue splendor, surrounded by original Rembrandts and unimaginable privilege. “Never came a baby into the world more wanted, with more love ready to welcome him than our Boy,” penned Flora Whitney soon after his birth. Gifted in his own right, the youthful writer/poet and Skull and Bones Yale honors grad matured over time into a strikingly handsome, charismatic adult who crackled with electric energy.

“Harry had magnetism and disarming friendliness,” associate John Hays Hammond later recalled. “I told him: ‘You could beat Teddy [Roosevelt] if you’d go into politics.’ ”

Whitney demurred from that path, though he was mentioned in 1906 as a possible heir to Tammany Hall’s Democratic kingmaker Tim Sullivan for a congressional seat and served briefly as New York commissioner of municipal statistics. As expected of his station, Harry dutifully sat on various boards – banking, mining, railway – and deported himself well. But none of this ignited his passion. In fact, he seemed to lack the internal drive that had propelled his father to the heights of business and politics. Instead, sport would become his life.

At the same time, credit the younger Whitney for betrothing himself in 1896 to a woman every bit as extraordinary and ahead of her time as his own mother. Gertrude Vanderbilt was beautiful, passionate, very much her own person. At the time of their nuptials, the great-grand-daughter of Commodore Cornelius Vanderbilt harbored an extraordinary talent that would blossom in years to come.

While most women of her class filled their days with society matters, Gertrude simmered with frustrated ambition. She was an accomplished sculptress, so good, in fact, that her work would one day stand on view in New York’s famed Metropolitan Museum of Art (as well as in her own Whitney Museum). But back then, she struggled – and her bitterness sometimes showed.

Early in her marriage, 26-year-old Gertrude scribbled savagely in her private journal: “Never, never in the world would I be willing to do mediocre things! I pity those who have no necessity to work. They have fallen from action into immobility and unrest … the dregs of humanity.”

She might have obliquely been referencing her husband, who even then had begun a slow drift away into a world she could not love or understand.

Gertrude yearned to express herself artistically and in the beginning, Whitney encouraged his talented wife, building her studios and hiring instructors. By 1915, the mother of three was sculpting long hours at a Greenwich Village space, producing graceful, usually pseudonymous works – including the prototype for her famous Titanic memorial, a massive granite monument that stands today near the Potomac in Washington.

“I fought to break down walls of half-scornful criticism,” she remembered long afterward, “based on no other concept than it wasn’t done by people in my position.”

Whitney’s days were increasingly consumed with play – yachting (aboard his $250,000 “Whileaway”), rowing, hunting (fox, grouse, African tigers), car racing, tennis, golf, and most of all, excelling on the polo field where he led American teams to international victories as a rare ten-goal player. His life may have appeared gratifyingly full, but looks could deceive. He consumed more alcohol as time passed, was plagued with increasingly severe headaches, and he battled depression. His deteriorating marital relationship could not have helped. In an unsent letter from 1914, Gertrude observed with brutal frankness: “Our mutual indifference to the pursuits and pleasures of the other forms no bond on which we might bridge our difficult moments.”

Horse racing was a pleasure Whitney enjoyed alone. In February 1904, W.C. Whitney passed away at age 62 in his Fifth Avenue mansion. The following June, 32-year-old Harry sat behind the broad expanse of his late father’s oak desk and informed a New York Times reporter he was simply too busy managing the family empire to devote time to the senior Whitney’s passion for horse racing.

Not so fast.

Just four months later, in a complete about-face, he splashed out $200,000 (of his $25 million inheritance) to purchase 19 Thoroughbreds from the Whitney estate bloodstock dispersal, staged spectacularly under lights and before a star-studded audience at Madison Square Garden. Among his acquisitions were future Hall of Fame champion Hamburg for $70,000 and a $5,500 mare named Daisy F., a hickory-tough winner of 23 races, by 1890 Kentucky Derby winner Riley. The Hamburg foal the latter carried in utero that evening was Jersey Lightning, a racing nonentity but later the dam of four stakes winners, including Regret.

The Derby

Harry Payne Whitney may or may not have lived up to his pedigree – but Regret surely did. Foaled in 1912 at Whitney’s leased Brookdale Farm in Lincroft, N.J., she shipped early in 1914 to the New York stable of James Rowe Sr. The future Hall of Fame horseman, who would ultimately train 10 Hall of Fame horses, recognized right off just what he had in this big, tomboyish filly.

Rowe thought so highly of Regret that instead of a selecting a traditional maiden race for her public unveiling, he opted for the Saratoga Special against experienced male rivals. She won in a hand-gallop on Aug. 8, 1914. A week later, she beat colts again in the Sanford Stakes, and seven days after that, she closed the door on her season with yet another sparkling victory over boys in the Hopeful. Regret was thereafter returned to her home base in New Jersey to bide time until spring.

Prior to 1914, the first 39 Kentucky Derbys had been regional, strictly Midwestern contests, drawing uninspired fields of local runners with rare exception. Churchill Downs manager and public-relations man extraordinaire Matt Winn was looking to change that when Donerail’s shocking 91-1 upset in 1913 provided an unexpected publicity windfall, dragging an otherwise nondescript race into the national spotlight. When the following May a remarkable gelding named Old Rosebud won, something truly special was brewing.

Winn had plumped the purse to $10,000-added by 1915 – nearly a quarter-million in today’s dollars – to pique the interest of top Eastern stables.(New York’s Belmont Stakes was worth $1,825 to the winner that year as opposed to $11,450 for the Derby.) The gregarious Winn then traveled east and did what he did best: He jabbered up a storm, marketing his showcase event as America’s “English Derby,” convincing racing’s elite there was nowhere else to be on May 8 than Louisville, Ky. Build it and they will come – and so they did.

Whitney’s stable arrived at Churchill on May 1, the day Lusitania set sail from New York to Liverpool. Regret reportedly had been working like a demon possessed on the Eastern seaboard, but now found herself cycling through a uniquely female mode – “in love” as one old-timer put it – anxious, off her feed, disliking the track surface, and generally unhappy with everything. All week, Rowe took turns with jockey Joe Notter (another future Hall of Famer) sleeping in the neighboring stall, where they could hear their tightly wound filly pacing the nights away.

On May 6, two days before the Derby, Regret worked the 10-furlong Derby distance in a yawning 2:08 3/5 and pulled up visibly tired. Rowe fretted and second-guessed himself nonstop; the press raved on.

“Regret has made many friends since her arrival,” enthused one Daily Racing Form correspondent. “She moves around the course like an old fashioned turf queen, has grown since last season, and can run fast and far.”

“For the first time since 1875,” wrote another, “a filly is regarded by the experts as ranking favorite, conceded the best chance to land the rich plum.”

A veteran trainer reportedly predicted: “Should Jimmy Rowe start Regret, string with him, for he will win for sure barring accident – because if he thought there was a possibility of her defeat, she would never go to post.”

DRF columnist Dr. M.M. Leach was among the journalistic legions giving the Whitney star a big thumbs-up, noting she had “exhibited such dazzling speed it would be foolish to oppose her. If the Derby this year is to be captured by one of the invaders from the east, I am of the opinion that brave little Broomstick’s chestnut daughter, fit and well on the day of the race, will be the one to turn the trick.” But, Leach went on to caution, “fillies are kittle-cattle and frequently disappoint in their three-year-old form.”

Derby week was hot, with horses training as early as 5 a.m. to avoid the high temperatures. Local hotel rooms filled to capacity; box and grandstand seating sold out in advance, though as DRF reported, “as usual, the great center field will be free as the air above to the public.” Rain came down sideways the night before and steam billowed from the earth on the morning of the big race. Rowe again held his breath, wondering just how his moody filly would react to a sloppy course.

Whitney and eight guests arrived in Louisville on Friday by special train; other cars would bring in Life magazine founder Andrew Miller; steel industrialists Daniel Gray Reid, and Price McKinney; New York millionaires and racing men Phil Dwyer and August Belmont; and scores of other headline-makers from across the country.

Two years earlier, militant British suffragist Emily Davison had sensationally dashed in front of King George V’s Anmer in the Derby at Epsom, bringing him down and suffering fatal injuries in the process. There would be none of that in Kentucky.

“Ladies shaped like hour-glasses wearing hats with six-furlong brims,” the great Red Smith later wrote, showed up en masse aboard open-air trolleys down Louisville’s Fourth Street to support their four-legged heroine with lusty cheers. Daily Racing Form compared the Downs that afternoon to Ascot or Longchamp in “times of peace,” festive and happy and packed to the rafters with cheering fans.

After bookmaking was outlawed in New York, California, and other major racing jurisdictions in 1908, Winn read the tea leaves: gambling middle-men would soon be relegated to history’s trash bin. He accordingly hauled out some 40 pari-mutuel machines long buried in the track’s storage, dusted them off, and returned them to service for the 12-day spring meet.

May 8 dawned sunny, windy, and warm. Harrows dragged the sodden track for hours leading up to the race card, eventually drying the surface to a reasonable degree. By race time, the track would be grudgingly fast – but not really. According to Winn, a record crowd had turned out to see for themselves what Whitney’s unbeaten filly could do.

At 5:18 p.m., Regret busted off the line as a 5-2 favorite over 15 rivals – the largest field in the race's 40-year history. In an utterly brilliant performance, she snatched the bit and led throughout under Notter’s stout hold, flitting lightly over the gummy-dry track Rowe had so worried about. When challenged by champion Pebbles, Notter simply jiggled the reins and Regret responded, jetting off by two lengths to a thunderous ovation from 50,000 fans to win under an aggressive hand ride. Afterward, she jogged saucily past the judges’ stand. She couldn’t have blown out a candle.

:: 1915 Kentucky Derby race chart

“One of the easiest victories of my career,” Notter described it five decades later.

Despite the magnitude and apparent ease of Regret’s historic victory, Derby results were shoved to Page 9, Section 3 of the next day’s Louisville Courier-Journal. The race was allotted a mere three inches of space on Page 2 of the New York Times sports section. News on May 9, 1915, was all about war and sunken ships. (Front pages: New York Tribune May 9, 1915; Daily Racing Form May, 9, 1915)


The Derby itself rounded a sharp corner that year. Never again would it be viewed as a local event of marginal significance. Winn got the home run required to turn the race into an American institution.

“The race needed only a victory by Regret to create some coast-to-coast publicity to really put it over. She did not fail us!” Winn crowed.

And it was a pivotal year for fillies and mares. Nine days after the Derby, Rhine Maiden captured Pimlico’s Preakness Stakes, the second leg in what would become the American Triple Crown. Lady Rotha took down Saratoga’s historic Travers that summer; legendary sprinter Pan Zareta won 15 races on the season, mostly over males; Waterblossom and Star Jasmine beat males repeatedly from New York to Kentucky; Comely and Coquette each won major East Coast races defeating the boys.

Regret ran once more in 1915, defeating Belmont Stakes victor The Finn at scale weights in the Saranac. At 4, she lost for the first time in the Saratoga Handicap and later was beaten a slim nose by stablemate Borrow in an unforgettable Brooklyn Handicap, outfinishing future Hall of Famers Old Rosebud and Roamer in the process. Whitney had declared before the race that Regret was his preferred winner that day should it come down to it, but Borrow’s jockey, Willie Knapp, seemed to forget his horse was entered merely to ensure a killer pace. He whipped and slashed to the finish with every ounce of his Hall of Fame skill to win by a flared nostril, after which a furious Whitney fired him. (Four years later, Knapp again donned the Whitney blue for homebred Upset’s victory over Man o’ War in the 1919 Sanford Memorial at Saratoga, marking the only career loss for that champion.)

:: Regret's lifetime past performances

When Regret bowed out of racing in 1917, she held an express ticket to the Hall of Fame when it was established 38 years later. (She was a member of the third class, inductees of 1957.) A winner in 9 of 11 starts at every major American distance, with as much as 129 pounds on her slender back, she had beaten most of the best male runners of her time and no filly or mare had ever crossed the wire in front of her. To his dying day in 1929, Rowe considered Regret the second-best racehorse he’d ever trained, better than the great Commando and brilliant Sysonby, superior to champions Peter Pan, Miss Woodford, Whisk Broom II, and Maskette – Hall of Famers, one and all – and behind only unconquerable Colin.

Whitney’s “pet,” as she was sometimes called, may have been a feminine icon on the racetrack in those steaming days of women’s suffrage, but in retirement she followed a traditional route in becoming a broodmare. Whitney remained one of America’s favorite sportsmen, and though health issues eventually took him off the polo field, he continued to breed great Thoroughbreds, including a record 191 stakes winners.

On rainy Travers Day of 1930, Harry Whitney stood alone along the backstretch rail at Saratoga, the track his father had revived from near-oblivion 29 years earlier. Field glasses in hand, he looked on as his highly touted homebred Whichone splashed by, matching stride for sloppy stride with newly minted Triple Crown winner Gallant Fox. He watched his horse take one bad step, then another and another as the colt’s fluid stride turned to sudden chop. He may not have noticed a mud-coated streak slip between horses on the far turn, en route to victory in the Midsummer Derby. That would have been 100-1 Jim Dandy.

With that, he pocketed his binoculars, ducked into a nearby car, and left the track.

Two months later, on Oct. 26, 1930, Whitney was dead at 58. A slight cold had segued into pneumonia, igniting a battle he simply could not win.

Whitney had been America’s leading owner six times by stable earnings – seven if you counted 1915 when his runners finished the season under another man’s name. He won a second Derby in 1927, with Whiskery.

He was eulogized through the wire services by no less a wordsmith than Damon Runyon:

“If we had such an elective office as first American sportsman, Harry Payne Whitney would have won it on popular vote by a large plurality years ago and held it to the hour of his death. … He was affable and easily approachable, and few men enjoyed his personal popularity. He had what the world of professional sport calls ‘class.’ … Other rich men might be starting better known horses, and of them the public would inquire: ‘are they trying?’ But you never heard that question asked of a Whitney horse. It was common knowledge that any time a Whitney took the track it was out to win, and if it didn’t win it was only because it wasn’t good enough. … On the turf, Whitney’s colors were far and away the most popular in this country, and in the mind of the racing public they stood for absolute honesty. ... We shall not soon see his like again.”


Suffragists soldiered on following Regret’s historic triumph, and women continued generating bold global headlines.

That autumn the silent movie “Inspiration” scandalized the world by featuring a fully nude female (actress Audrey Munson). Edith Cavell, a 50-year-old British nurse based in Brussels, was arrested in August by German authorities after aiding allied soldiers. She was charged with treason and executed by firing squad. Nearly two years later, exotic dancer-turned-German spy Mata Hari suffered an identical fate before a team of French marksmen.

In January 1915, the U.S. House of Representatives contemplated amending the Constitution to enfranchise women. Women filled the spectators’ gallery with loud hisses when Ohio Rep. Stanley Bowdle took the floor to say: “While women are beautiful, their feet are beautiful, their ankles are beautiful – their beauty is disturbing to business … and they are not interested in the state.” The bill was rejected on a 204-174 vote, pouring fuel onto an already raging fire.

On Oct. 23, more than 40,000 angry women and 5,000 supportive men from every state marched down Manhattan’s Fifth Avenue, not asking for, but demanding the right to vote. A week later, men in four eastern states – including New York and Massachusetts – responded at the ballot box with a resounding “No!”

But change was coming. On Aug. 26, 1920, after a century of marches, pickets, hunger strikes, and assorted civil disobedience on the part of American women, Secretary of State Bainbridge Colby formally ratified the 19th Amendment to the Constitution, wherein was declared that “the right of citizens of the United States to vote shall not be denied or abridged on account of sex.”

At that moment, Regret was roaming the pastoral blue grass, pregnant by European-bred Belmont Stakes winner Johren with the third of 11 eventual offspring. A half-decade earlier, DRF’s Leach had predicted her breeding value would be great and that “a stud colt from Regret by some fashionably-bred English horse should not find a Melbourne Cup, a Grand Prix, or even an Epsom Derby beyond his capabilities.” But he was wrong; not one of her foals held the proverbial candle to her. All were ordinary – on the racetrack and, for the most part, in the breeding shed.

Regret’s female line survives today, but without much shouting. Eyjur, the 2005 Brazilian champion miler, can be traced back eight generations to the 1915 Derby winner, while 2012 Danzig Stakes victor Jake N Elwood was separated by nine bottom-line generations to the historic filly.

Clearly, Regret’s most enduring legacy flows not through the veins of modern Thoroughbreds. It is inscribed most indelibly in the fragile century-old pages of Daily Racing Form’s chart book on the date of May 8, 1915.

Though a fair number of fillies have attempted the feat – 40 thus far – 65 years passed before Genuine Risk returned a winner in the Kentucky Derby, and it was eight more years before Winning Colors added her name to the short list of female conquerors. No filly has run for the roses since Devil May Care’s 10th-place finish in 2010.

To be sure, other equine Amazons have emerged through the years – Gallorette, Twilight Tear, and Busher in the 1940s; Two Lea and Silver Spoon (1950s); sprinters Affectionately and Ta Wee (1960s); iron mares Dahlia, Shuvee, and Typecast (1970s); the brilliant Lady’s Secret and unbeaten Personal Ensign (1980s); Serena’s Song (1990s); Belmont Stakes heroine Rags to Riches (2000s); and most recently the dynamic Horse of the Year trio of Rachel Alexandra, Zenyatta, and Havre de Grace. Each beat males in big-time events, earning lavish praise for doing what “Whitney’s pet” had accomplished on a routine basis on nearly every afternoon of her racing career.

:: Kentucky Derby fillies as broodmares

Regret was the first of her kind to scale American racing’s highest mountain. She remains on the peak to this day, a beautiful, blaze-faced phantom, residing at the crossroads of history and legend.