Sir Barton, foaled at Hamburg Place, Lexington, Ky., was the first Triple Crown winner in 1919.
Purchased for $10,000, Sir Barton was one of racing's best rags-to-roses stories. The chestnut colt went 0-for-6 as a 2-year-old and was entered in the Kentucky Derby to set the pace for his stablemate. Instead, with jockey John Loftus, the H.G. Bedwell-trained colt became the first winner of the Derby, the Preakness and Belmont Stakes.
Sir Barton finished his career with a record of 13 wins from 31 starts and $116,857 in earnings.
Gallant Fox, with jockey Earl Sande, wears the roses after winning the 1930 Kentucky Derby. He went on to win the Triple Crown. This bay colt didn't appear bound for greatness taking only 2-for-7 as a 2-year-old. The following year he won nine times in 10 starts for rider Earl Sande, trainer "Sunny" Jim Fitzsimmons and owner Belair Stud.
Gallant Fox retired to stud duty after his 3-year-old season with a lifetime record of 11 wins from 17 starts and $328,165 in earnings. He earned further distinction in the breeding shed by siring Omaha and becoming the only Triple Crown winner to sire another.
Omaha, with jockey Willie Saunders, approaches the finish line to win the 61st running of the Kentucky Derby in 1935.
This chestnut colt made the Triple Crown a family affair for trainer "Sunny" Jim Fitzsimmons and owner Belair Stud, who teamed up to win the series with his sire, Gallant Fox, in 1930. He was riden by jockey Willie Sanders throughout his Triple Crown campaign.
Omaha retired with a lifetime record of nine wins from 22 starts and $154,755 in earnings.
War Admiral wins the Kentucky Derby two lengths ahead of his challenger, Pompoon, at Churchill Downs in 1937. This smallish brown colt was a son of the great Man o' War, though he bore little physical resemblance. War Admiral earned eight wins from eight races in his 3-year-old season, including his Triple Crown victories under jockey Charles Kurtsinge, trainer George Conway and owner Glen Riddle Farms.
He continued to be a dominating force through his 5-year-old season, winning eight more stakes races but losing to Seabiscuit in a much-heralded East vs. West match race at Pimlico. War Admiral retired to a successful second career as a sire with a record of 21 wins from 26 starts and $273,240 in earnings.
Known as "Mr. Longtail" for his flowing tress, Whirlaway was the horse that put owner Warren Wright Sr.'s storied Calumet Farm on the map in 1941.
Whirlaway was difficult to ride because of his habit of going wide on the turns, so trainer Ben Jones fitted the chestnut colt with blinkers and engaged the services of riding great Eddie Arcaro. The result: an eight-length Kentucky Derby victory in track record time of 2:01 2/5 — a mark that stood for 20 years — and the fifth Triple Crown.
The first thoroughbred to win more than half a million dollars, Whirlaway was retired with 32 victories from 60 starts and $561,161 in earnings.
Count Fleet, with jockey John Longden up, crosses the finish line to win the 69th running of the Kentucky Derby in 1943. A fast brown colt, Count Fleet was assigned the highest weight ever — 132 pounds — in the Experimental Free Handicap, a method in which Jockey Club racing secretaries assess the accomplishments of sophomores.
Owned by Mr. and Mrs. John D. Hertz, the Count finished his career by going 6-for-6 as a 3-year-old for trainer G.D. Cameron and jockey Johnny Longden, winning the Wood Memorial and Withers Stakes in addition to the Triple Crown races.
Assault thunders down to the finish line to win the 72nd Kentucky Derby in 1946. One of just two Texas-breds ever to win the Kentucky Derby, Assault also defied the odds by developing into a top-flight racehorse despite a serious injury that left him with a crooked right foreleg.
After taking only two wins as a 2-year-old for Robert Kleberg Jr.'s King Ranch, the Max Hirsch-trained chestnut colt rebounded as a 3-year-old to win eight times in 15 starts.
The son of Bold Venture won his last race at the age of 7 before being retired with a record of 18 wins in 42 starts and $675,470 in earnings.
Citation crosses the finish line to win the Kentucky Derby in 1948. Called the greatest racehorse of the century along with Man o' War, Citation gave Calumet Farm and trainer Ben Jones their second Triple Crown winner in seven years.
The bay colt won 27 of 29 starts in his 2- and 3-year-old seasons. As a 3-year-old, he won 15 in a row, including the Triple Crown races. He ran the winning streak to a modern record 16 straight in 1950, after missing all of 1949 with ankle and tendon injuries.
Secretariat and jockey Ron Turcotte take the 99th Kentucky Derby in 1973 with a 2 1/2-length victory over Sham in 1:59 2/5, the only sub 2-minute Derby in history until Monarchos stopped the clock in 1:59.97 in 2001.
After beating Sham by the same margin in the Preakness, the Claiborne Farm color-bearer turned in what many consider the best performance by a thoroughbred, beating four rivals in the Belmont Stakes by 31 lengths.
Seattle Slew crosses finish line to win 103rd Kentucky Derby in 1977. Slew entered the Kentucky Derby as the 1-2 favorite after running his record to 6-for-6. He gave his owners and trainer Billy Turner Jr. a horrible scare by nearly falling at the break and getting away about a half-dozen lengths behind the leaders. Jockey Jean Cruguet quickly rushed the dark bay colt up, with Slew slowly drawing away in the stretch to post a 1 ¾-length victory. Seattle Slew's wins in the Preakness and Belmont Stakes were far less eventful and much easier. He remained a force in the handicap ranks through his 4-year-old season, when he survived a near-fatal illness and returned to beat fellow Triple Crown winner Affirmed in the Marlboro Cup before being retired with a record of 14 wins in 17 starts, and earnings of $1,208,726.
Affirmed, with jockey Steve Cauthen in the saddle heads for the finish line during the 104th Kentucky Derby in 1978. Bred and raced by Louis Wolfson's Harbor View Farm, the chestnut colt battled his arch rival Alydar six times when both were 2-year-olds, emerging victorious four times. They continued to race as 3-year-olds, with Affirmed and jockey Steve Cauthen prevailing over Alydar and Jorge Velasquez by 1½-lengths in the Kentucky Derby, a neck in the Preakness and a head in the Belmont. By year's end, the two had met 10 times, with Affirmed winning seven races.
The son of Exclusive Native was retired with a record of 22 wins from 26 starts and earnings of $2,393,818, making him the first horse to compile a bankroll of more than $2 million.