Curlin winning the 2007 Preakness. (Jim McCue for Maryland Jockey Club)
By Maribeth Kalinich
Eighteen sires and sons have won the Preakness including sire-son Triple Crown winners and two sets that span three generations. The Preakness is a legacy race.
Man o’ War won the Preakness Stakes in 1920, the year after Sir Barton set the standard for the Triple Crown.
The stalwart colt by Fair Play out of Rock Sand mare Mahubah was bred in Kentucky by August Belmont Jr., and owned by Sam Riddle of Glen Riddle Farm, in Belair, Md., Man o’ War was the original “Big Red,” and big he was.
Trained by Louis Feusteland ridden by Clarence Kumar, he completed the then 1-1/8 mile course in 1:51.60 to collect a purse of $40,000. The chestnut colt beat a horse whose name would become synonymous with what happened in this year’s Kentucky Derby—Upset.
Man o’ War won the Preakness and Belmont Stakes but was not entered in the 1920 Kentucky Derby because Riddle did not believe in racing at the distance of 10 furlongs so early in a young horse’s career.
Man o’ War’s son, War Admiral, a Kentucky homebred by Riddle, won the Preakness in 1937. He would win the inaugural Pimlico Special in 1937 only to lose the following year’s edition run as the most famous match race in racing history against Seabiscuit.
War Admiral, out of the mare Brushup by Sweep, ran the Preakness just a week after his Derby victory. After again acting up at the start, the big colt went to the lead early but had trouble negotiating the turns. Pompoon saved ground along the rail and closed alongside War Admiral as they exited the last turn. The two horses dueled down the stretch with War Admiral finally prevailing by a head.
Riddle’s pride would go on to win the Belmont Stakes and the Triple Crown. But the victory came at a price.
War Admiral had struck the quarter of his right front fore-foot when stumbling at the gate, which left a gaping wound. During the race, his jockey did not notice that anything was amiss. But when led into the winner’s circle, his connections found that his belly and legs were covered with blood. He returned in October to win three more races, including the Washington Handicap and the aforementioned Pimlico Special.
The most renowned sire and son pair is Gallant Fox (1930) and his son Omaha (1935). Owned by William Woodward Sr. of Belair Stud, both went on to be Triple Crown winners.
Both Gallant Fox and Omaha were trained by “Sunny Jim” Fitzsimmons. In the irons, respectively, were future Hall of Famers Earle Sande and Willie Saunders.
With the distance of the Preakness extended from 1-1/8 miles in 1924 to its current distance of 1-3/16 miles, both colts competed at the same length. Although, they did not finish with the same time. Omaha would best his father’s 2:00.60 with 1:58.40.
The Triple Crown races were not run in same order every year in the early 20th Century.
Gallant Fox ran in the Preakness on May 9 before the Derby held on May 17. The Belmont Stakes was contested June 7.
The Preakness was run before the Derby eleven times. May 12, 1917, and May 13, 1922, the Preakness and the Derby were run on the same day. Since 1932, the order of Triple Crown races has been the Kentucky Derby, the Preakness two weeks later, then the Belmont in June.
The order of Triple Crown races may have been set into the future but the spacing between races wasn’t set for several decades. Omaha won his Kentucky Derby on May 4 and was presented the Woodlawn Vase for the Preakness May 11. But he didn’t take time off before the Belmont Stakes on June 8. He ran in the Withers at Aqueduct placing second to Rosemont by 1-1/2 lengths.
June 22 Omaha ran in the Brooklyn Handicap and was crushed by Discovery. So Sunny Jim gave him some time off before starting his Triple Crown champ in the Arlington Classic. Omaha set the track record that day.
Bold Venture would be the victor in 1936. His son, Assault, would win 10 years later in 1946.
Bold Venture was ridden by the infamous George Woolf who would two years later take over for Red Pollard on Seabiscuit in the Match Race. The colt was trained by legendary Max Hirsch and owned by Morton Schwartz. Schwartz was a member of the New York Stock Exchange and a major breeder/owner of Thoroughbreds.
The son of St. Germans (GB) out of Ultimus mare Possible, Bold Venture won six of his 11 starts including the Kentucky Derby. He is the only Kentucky Derby Winner to sire two other Kentucky Derby winners.
Bold Venture ran the 1 3/16-mile course in 1:59 flat and collected a purse of $50,000.
The chestnut colt suffered a bowed tendon & retired before the Belmont Stakes.
Owner Morton L. Schwartz sold Bold Venture to Robert J. Kleberg Jr. for a reported $40,000 for breeding. Although Bold Venture did not have immediate success as a stallion in Kentucky, he then stood at Kleberg’s King Ranch in Texas, and while there he sired Assault, the 1946 Triple Crown champion, and Middleground, winner of the 1950 Kentucky Derby and Belmont Stakes.
Bold Venture died in 1958 at age twenty-five.
Assault would collect a purse much higher than his sire. In 1946 the award was $160,000, big money in 1946.
The first of our sire-son triple generations is Polynesian (1945), Native Dancer (1953) and Kauai King (1956). Two missed the Triple Crown by one race. Native Dancer won the Preakness and Belmont and lost the Derby to Dark Star by a neck.
Kauai King won the Derby and the Preakness but finished fourth in the Belmont Stakes behind Amberoid.
Amberoid would prove to be an important part of history. He gave trainer Lucien Lauren his first Belmont Stakes win.
In 1948, Citation won both the Preakness and the Triple Crown. His son, Fabius would win the Preakness in 1956.
The next trio of sire-sons set up the most historic series of events in Thoroughbred horse racing history. In 1957, Bold Ruler would win the Preakness and in 1970 he would sire Secretariat.
Three years later, Secretariat would stun the world winning the Triple Crown and setting records in each of the three races.
Risen Star, son of Secretariat, would win the Preakness in 1988.
Summer Squall was the Preakness champion in 1990 and his son, the ill-fated Charismatic won in 1999 with the late Chris Antley aboard.
And our last pair is successful sire Curlin who won the Preakness in 2007 and then sired Exaggerator, the 2016 victor.
Curlin beat Street Sense by a head in one of the most exciting Preakness finishes ever. (I say that about most Preakness finishes, but this one was!) The two sturdy colts battled down to the wire under steely jockeys Robby Albarado, the victor, and Calvin Borel, the unlucky loser.
Exaggerator would thrill the crowd nine years later and give brother team jockey Kent Desomeaux and trainer Keith Desomeaux their first Preakness.
Skippylongstocking, the son of Exaggerator, started in the 147th Preakness finishing fifth and is nominated to the Grade 3, Pimlico Special on May 18.
2013 Preakness champ Oxbow’s son Happy Jack finished eighth and the son of 2007 Preakness winner Curlin finished ninth the same year.
In 2023, there were no sire-son combos but Good Magic deserved bragging rights with three starters – second place finisher Blazing Sevens, Kentucky Derby champion Mage and Perform, who had an automatic berth winning the Federico Tesio.
Most links in this story will take you to American Classic Pedigrees. Take time and browse.
