How Kentucky Derby Winners Have Fared in Preakness Stakes

May 20th, 2023

The 13 Triple Crown winners captured both the Kentucky Derby (G1) and Preakness (G1) en route to the Belmont (G1), but that just scratches the surface of the impact of the Run for the Roses on the middle jewel.

In nearly 150 years, a total of 36 horses won both the Derby and Preakness, while 26 Derby winners have placed in the Preakness. Moreover, 48 others who lost the Derby won the Preakness.

Yet these strong correlations only began to emerge after the two classics had already existed for about a half-century. The Preakness was first run in 1873, preceding the Derby that was inaugurated in 1875.

Unlike the historical continuity of the Derby, which will be held for the 150th time at Churchill Downs in 2024, the Preakness has had a more tumultuous history. The stakes was not run at all in 1891-93, and a version of the race was contested in first at Morris Park in New York in 1890 and then at Gravesend Race Track on Coney Island from 1894-1908. After the Preakness was restored to Pimlico in 1909, the stage was set for its development into the classic we know today.

They Wore the Crown

Not until 1919 did a Derby winner try the Preakness – Sir Barton, who became the first to sweep the three races that we know as the Triple Crown. Before then, very few Derby runners even competed in the Preakness and only two won. Hindus, last of seven in the 1900 Derby, captured the Preakness in its New York era, while War Cloud, who won a division of the 1918 Preakness, was wheeling back four days after his fourth to Hall of Famer Exterminator in the Derby.

The floodgates opened once Gallant Fox (1930) swept the three classics, firmly establishing the Triple Crown concept. His year reflects a transitional period when the Preakness was held before the Derby from 1923 to 1931, a byproduct of 1922 when the two races were actually run on the same day. The Triple Crown order of Derby-Preakness-Belmont was fixed in 1932, though the current spacing between the races dates to 1969.

Gallant Fox’s Omaha (1935) also completed the sweep, still standing as the only father-son Triple Crown-winning tandem. In rapid succession came legends War Admiral (1937), Whirlaway (1941), Count Fleet (1943), Assault (1946), and Citation (1948).

The mighty Secretariat (1973) ended the Triple Crown drought in spectacularly record-setting fashion, followed by Seattle Slew (1977) and Affirmed (1978). It took another 37 years for a champion to win the Derby, Preakness, and Belmont, in the form of American Pharoah (2015). Just three years later, Justify (2018) added his name to the roll of honor as the 13th Triple Crown winner.

Dual Classic Winners

Aside from the thirteen Triple Crown winners, 23 horses prevailed in the Derby and Preakness, but not the Belmont. Bookending this list are Burgoo King (1932), who did not run in the Belmont because of an injury, and California Chrome (2014), fourth in the Belmont after a troubled start.

The other dual classic winners include Bold Venture (1936), Pensive (1944), Tim Tam (1958), Carry Back (1961), Northern Dancer (1964), Kauai King (1966), Forward Pass (1968), Majestic Prince (1969), Canonero II (1971), Spectacular Bid (1979), Pleasant Colony (1981), Alysheba (1987), Sunday Silence (1989), Silver Charm (1997), Real Quiet (1998), Charismatic (1999), War Emblem (2002), Funny Cide (2003), Smarty Jones (2004), Big Brown (2008), and I’ll Have Another (2012).

Additionally, 26 official Derby winners have placed in the Preakness. The first two on this list did it in reverse order. Whiskery (1927), third to Bostonian in the May 9 Preakness, gained revenge in the May 14 Derby. Twenty Grand (1931), runner-up to Mate at Pimlico on May 9, turned the tables in the Derby a week later.

The rest won the Derby first before collecting a placing in the Preakness – Cavalcade (second in 1934), Gallahadion (third in 1940), Hoop Jr. (second in 1945), Middleground (second in 1950), Needles (second in 1956), Iron Liege (second in 1957), Chateaugay (second in 1963), Proud Clarion (third in 1967), Cannonade (third in 1974), Foolish Pleasure (second in 1975), Bold Forbes (third in 1976), Genuine Risk (second in 1980), Ferdinand (second in 1986), Winning Colors (third in 1988), Unbridled (second in 1990), Go for Gin (second in 1994), Thunder Gulch (third in 1995), Fusaichi Pegasus (second in 2000), Giacomo (third in 2005), Street Sense (second in 2007), Mine That Bird (second in 2009), Animal Kingdom (second in 2011), Nyquist (third in 2016), and Authentic (just missed in the photo in 2020).

Between the 36 who turned the Derby-Preakness double and the 26 Derby winners who placed at Pimlico, a total of 62 who wore the roses at Churchill Downs finished in the top three in the middle jewel. Not all Derby winners, though, followed up their Derby wins with another top performance at Pimlico; 22 failed to win or place in the Preakness, most recently Always Dreaming (eighth in 2017).

Still, the percentage of in-the-money Preakness efforts by Derby winners – nearly 74% – remains impressive. Mage will try to enhance that stat when he lines up in Saturday’s 148th Preakness.