In today’s world of Thoroughbred horse racing, the path to winning an Eclipse award as champion 2-year-old is relatively clear. First, you win a maiden race for horses who have never won a race before. Then, you try to win at least one graded stakes race (preferably a Grade 1) and hopefully more; finally, you win either the Breeders’ Cup Juvenile or Breeders’ Cup Juvenile Fillies to become the clear-cut champion of your division.

With star horses typically running once a month during the peak of the season, a 2-year-old championship can be sewn up in about three or four months. But many years ago — back before the Breeders’ Cup, and back when horses ran more frequently — it was possible for a talented horse to achieve leadership of the division in much less time. In fact, during the summer of 1914 at Saratoga racetrack, the legendary filly Regret stamped herself as the champion 2-year-old filly by going from an unraced maiden to a three-time stakes winner in just 15 days.

Yes — 15 days.

Of course, some things never change. Even in 1914, Saratoga was known for its top-notch program of races for 2-year-olds, with the major stakes races including the Saratoga Special, Sanford Memorial, and Hopeful Stakes, all of which still exist today.

With Saratoga carrying such prestige, it was only natural that a racing sportsmen like Harry Payne Whitney — owner and breeder of Regret — would want to target the meet with his very best horses, including Regret. At the start of the meet, Regret was an unraced and unproven filly, but one with a lot of potential. Her sire was Broomstick, a rising star as a stallion that had been the leading sire of 1913, and Regret’s maternal grandsire was Hamburg, a renowned runner in the 1890s that had won 16 of his 21 races, including the 2 ¼-mile Brighton Cup by an astonishing 100 lengths.

Right from the start, trainer James Rowe Sr. was impressed with Regret, to the extent that he didn’t even bother running her in a maiden race. Instead, Regret’s debut came in the six-furlong Saratoga Special on Aug. 8, where she would not only face proven and experienced rivals, but colts as well.

Nevertheless, Regret’s reputation preceded her and she was sent off as the favorite against seven opponents. With jockey Joe Notter in the saddle, she burst out of the starting gate fastest of all and quickly opened up a three-length lead. After being challenged briefly with two furlongs to go, she cruised home with “speed in reserve” per the Daily Racing Form to win by a length in the track-record time of 1:11 3/5.

Regret’s performance would have been impressive even for a veteran racehorse, but coming from a 2-year-old filly making her first start, it was astonishing. A week later, she returned in the six-furlong Sanford Memorial — where she once again faced colts — and was even more impressive. Carrying 127 pounds on a track labeled “slow,” Regret set the pace again before winning easily by 1 ½ lengths while “under restraint throughout,” despite the fact that she was carrying 14 pounds more than the runner-up and 20 pounds more than the third-place finisher.

Brilliance? Check. Ability to carry high weights? Check. The one major question Regret still had to answer was the question of heart; she could sprint her rivals off their feet, but did she have the courage to overcome adversity and prevail under less-than-ideal circumstances?

The Hopeful Stakes. (Blood-Horse/Keeneland Library - Cook)

The answer came on Aug. 22 in the Hopeful Stakes, the culmination of Saratoga’s 2-year-old racing program. Rain left the track very heavy and tiring, and Regret — perhaps not caring for the conditions — found herself off the pace for the first time in her career, racing nearly seven lengths off the lead and in sixth place partway through the race. But like a champion, she rose to the occasion, unleashing a powerful rally in the homestretch to put herself back in contention. She was still in third place with a furlong to go, but she had the leaders measured, and dug in to win by a determined half-length while conceding 13 pounds to the runner-up.

Thus, in the span of 15 days, Regret had conquered the best 2-year-olds at Saratoga while carrying high weights and handling a wide variety of track conditions. As if to further demonstrate Regret’s superiority, one of the colts that she beat on two occasions — Pebbles — would end the year with five stakes wins, earning recognition as the champion 2-year-old colt.

But there could be no denying that Regret was the overall champion of the division, even though the Hopeful Stakes was her final race of the year. In 1915, she returned better than ever to make history with a decisive two-length victory over Pebbles in the Kentucky Derby, becoming the first filly to win the run for the roses.

More than a century after her 15-day championship campaign at Saratoga, Regret remains one of just four horses to have swept the Saratoga Special, Sanford Memorial, and Hopeful Stakes. Even at the time, Regret’s accomplishments were special; today, they are almost impossible to imagine.