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Mad Hatter: A Durable & Temperamental Champion

Mad Hatter, undated. This photo is courtesy of the Keeneland Library Cook Collection.
Mad Hatter, undated. This photo is courtesy of the Keeneland Library Cook Collection.

From 1918 to 1924 an eye-catching, temperamental colt named Mad Hatter continuously made headlines for beating the best horses of his time - or for losing to them by inches.

Mad Hatter was sired by Fair Play out of the Rock Sand mare Madcap, the same cross on which his breeder August Belmont Jr. would also produce the likes of the great Man o’ War. He was a beautifully built dark bay horse with a good shoulder and clean legs (American Classic Pedigrees).

August Belmont immediately took a liking to his “overgrown” colt and knew that a slower beginning to the horse’s career would help him develop into a grand older horse. Belmont elected to race Mad Hatter himself during his juvenile season; the colt was sent to the post just ten times in 1918 and though he only won two of those races, he managed to capture the Bellerose Stakes going five furlongs.

Mad Hatter was sold to Harry F. Sinclair’s Rancocas Stable prior to his three-year-old season. Sinclair sent the horse to Sam Hildreth for conditioning.

Hildreth also chose to take things slowly with Mad Hatter and kept him out of the races until later in the year so that he would be “fresh and fully developed” for the stakes races held late in the season. The waiting paid off as Mad Hatter won three stakes from seven starts as a three-year-old, including the fourteen furlong Latonia Stakes in which his victory was described as an “easy one” in which he was “only galloping to ultimately win, with his rider looking around to view the struggle between Sway and Stockwell for second place”.

The same year, a three-year-old colt named Sir Barton was etching his name in horse racing history by becoming the very first Triple Crown winner. Though few knew it at the time, Sir Barton’s wins in the Kentucky Derby, Preakness Stakes, and Belmont Stakes would become a marker for greatness in American horse racing.

Mad Hatter first met Sir Barton in the Maryland Handicap; Sir Barton got to the wire first while carrying 133 pounds compared to Mad Hatter’s 106. They faced each other again in November for the Pimlico Autumn Handicap and this time Mad Hatter easily defeated the Triple Crown winner while carrying 111 pounds compared to Sir Barton’s heavy burden of 132.

“That Sam C. Hildreth has one of the greatest three-year-olds of the year in Mad Hatter, was proved quite conclusively here today when this fine son of Fair Play just romped off with the Pimlico Autumn Handicap at a mile and a quarter and made his victory all the more impressive by defeating the great Sir Barton, pride of the stable of J K L Ross,” published the Montreal Gazette. “Mad Hatter won in a gallop and was four lengths in front to Bridesman, while Sir Barton came in third, eight lengths back of the second horse and took the worst defeat that has been administered to him this year.”

Mad Hatter (#2) follows Exterminator (#1), undated. Photo courtesy of the Keeneland Library Cook Collection.
Mad Hatter (#2) follows Exterminator (#1), undated. Photo courtesy of the Keeneland Library Cook Collection.

By his four-year-old season, Mad Hatter was considered one of the best horses on the track. Even as the similarly bred Man o’ War shocked the nation with his outstanding performances as a two-year-old, Mad Hatter’s seven-race win streak that year had journalists writing that he was “just about the best horse now racing over any distance greater than a mile.”

In 1920 he notably won the Yorktown Handicap in which he “ran as if he outclassed the other two” and just four days later again beat Sir Barton and the Triple Crown winner’s revered stablemate Billy Kelly in the Pimlico Serial #2.

“Mad Hatter’s race was the best one he has run this year, if not in his entire career,” one reporter wrote of his Pimlico Serial victory. “His displayed remarkable speed from a slow start and was much the best though carrying equal weight with his rivals.”

Three days later he captured the Bowie Stakes by a nose over a field that included the likes of the great handicap horse Exterminator. The race was so close that by some angles it looked as though the second-place horse Boniface had won.

The Bowie Stakes marked the seventh straight win for Mad Hatter, but his streak would come to an end two days later when Billy Kelly and Sir Barton turned the tables on him in the Pimlico Serial #3. A bad start in which Mad Hatter was left far behind was blamed for the defeat; the son of Fair Play expended too much energy to gain position in the early stages and though at the top of the stretch it looked as though he would win, Billy Kelly had much more run left and was able to pass him while Sir Barton ground Mad Hatter down by a nose for second.

As Mad Hatter’s celebrity grew, so did the weights he was forced to carry. Despite the heavy burden, Mad Hatter raced twenty times during his five-year-old season in 1921 and only finished unplaced in two of these starts.

He began the year with a romp over Exterminator in the Kings County Handicap while establishing a track record. Among his notable wins that year were the Metropolitan Handicap, October Handicap, and Jockey Club Gold Cup. Though 1921 was a successful year for Mad Hatter, his inability to win at Saratoga that year and his plethora of losses by just inches were cause for frustration for fans, horseplayers, and his connections.

“No horse has caused more disappointment to his stable connections during the Saratoga meeting than Mad Hatter, which came here one of the star long-distance performers of the Rancocas string,” the Daily Racing Form published. “In three stakes he finished second, beaten only by a matter of inches, and on all three occasions he had victory within his grasp a sixteenth of a mile out.”

“He just seemed determined that he would not win a race at the meeting,” jockey Laverne Fator said. “He would make a dangerous move at the head of the stretch, and just when it appeared as though he was going to win he would make a fatal bobble near the end.”

Nevertheless, many of his losses, including the one to Yellow Hand in the Saratoga Handicap while carrying 132 pounds compared to the winning gelding’s 120, were still considered brilliant performances and he was named the Co-Champion Handicap Male of 1921.

Mad Hatter (#2) finishes second to Exterminator (#3) in the Merchants and Citizens Handicap at Saratoga. Photo courtesy of the Keeneland Library Cook Collection.
Mad Hatter finishes second to Exterminator (#3) in the Merchants and Citizens Handicap at Saratoga. Photo courtesy of the Keeneland Library Cook Collection.

Mad Hatter was often described in newspapers as a temperamental horse. His riders were not permitted to carry a crop, as the use of it would cause him to flinch and bear either in or out. He was known for his immense speed and ability to carry that speed over long distances, though only when he wanted to. If urged on, Mad Hatter was inclined to slow down. If asked to slow down, he would fight hard against his jockey. He loved to run, but only the way he wanted to.

“No horse in training, with the possible exception of Lucky Hour, has more speed when Mad Hatter is in a generous mood.”

The general consensus was that Mad Hatter came out of his five-year-old season a better-looking horse than ever. Blessed with durability and soundness, the son of Fair Play was ready for another strenuous campaign of twenty-one races, the most he would ever run in a single season, in 1922.

He again started the year by winning the Kings County Handicap and soon after captured the Metropolitan Handicap in record time and the two-mile Jockey Club Gold Cup, all three for the second time. After a period of three hard races in a row and a two-day turnaround time caused Mad Hatter to lose the October Handicap, the decision was made to give him a brief period of rest before he would contest in several other rich stakes events.

“In the meantime,” wrote the Daily Racing Form after the October Handicap, “twenty-seven victories, twenty seconds, and twelve thirds for a total of $162,325 out of seventy-two starts is a record to be proud of, especially when the horse that did it is sound and ready for other battles after a period of well-earned rest.”

By the end of 1922, Mad Hatter had also captured the Champlain Handicap and Pierrepont Handicap for a total of five wins. He had finished second nine times and third on two occasions. His total earnings of $44,250 that year cemented him as one of the highest-earning horses that turf had ever seen, surpassed only by Man o’ War, Exterminator, Domino, Sysonby, and Colin.

“None of his victories have been achieved with a feather on his back,” the Border Cities Star printed. “All have been gained with steadying imposts - the majority with 128 pounds or more - and many have been won by the narrowest of margins in finishes calling for the last atom of speed and courage.”

Mad Hatter’s career began to wind down after his six-year-old season. He won just once in seven starts in 1923, capturing the six-furlong Toboggan Handicap, and was unplaced in his six other races.

He managed to regain some of the form of his old days in 1924, winning three of his six starts: the Suburban Handicap, Queens County Handicap, and Laurelton Handicap.

“Old Mad Hatter and Jockey Earl Sande proved too much for the fast sprinters in the Laurelton Handicap, the feature of a good program,” the DRF published. “Mad Hatter has won at all distances with big weight up and still retains some of the speed of his early racing days.”

His victory in the 1924 Suburban Handicap came against his full-brother Mad Play. Mad Play was five years younger than Mad Hatter and was a very talented racehorse himself; among his many notable victories was the 1924 Belmont Stakes.

While still capable of winning in the sport’s premier races, it was decided that Mat Hatter would not race in 1925 and he was finally retired at nine years old. Mad Hatter was never able to reproduce himself while at Harry Payne Whitney’s Stud, though he is credited with siring 22 or 23 stakes winners from 177 foals.

Mad Hatter’s long, illustrious career is something we will likely never see again in modern-day horse racing. The sound, durable son of Fair Play crossed the wire ninety-one times, sometimes racing in stakes that were held just days apart. He beat many of the best horses of his era at distances ranging from five furlongs to two miles.

In seven seasons of racing, he won thirty-two starts, finished second in twenty-one, and ran third in fourteen. His earnings of $194,225 is equivalent to almost $3.3 million in 2023.

Mad Hatter might not be even mentioned when racing fans think of their favorite racehorses from this era long past. Nevertheless, his toughness and do-it-my-way personality still enchants those who hear his story.

Mad Hatter Thoroughbred racehorse
Mad Hatter, wikimedia commons. Public Domain.

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