Pedigree fun facts: 2021 Kentucky Derby

Here’s a look at some of the fascinating pedigree angles in the 147th Run for the Roses. For deeper details on this spring’s major prep winners, see the pedigree fun facts section. 

Two-time leading sire Into Mischief smashed the North American progeny earnings record in 2020 – bankrolling more than $22.1 million – with the help of his Kentucky Derby-winning son, Authentic. By adding the Breeders’ Cup Classic (G1) last November, Authentic surpassed $7.1 million in earnings for the season. 

Now Into Mischief could rewrite the record book again by siring a second straight Kentucky Derby winner. No stallion has sired back-to-back winners, with the nearest being two years in between. Even that’s happened only twice. After The Finn was responsible for Zev (1923) and Flying Ebony (1925), it took another five decades for Exclusive Native to match him with Affirmed (1978) and Genuine Risk (1980).

Into Mischief has three chances – the most of any sire in Derby 147 – and quality to go along with the quantity in Blue Grass (G2) runner-up Highly Motivated, Risen Star (G2) hero Mandaloun, and Florida Derby (G1) second Soup and Sandwich. 

If Into Mischief colts can run one-two, it would be the first time that a sire had the cold Derby exacta since Calumet’s legendary Bull Lea in 1948. That was the year Triple Crown sweeper Citation beat stablemate and fellow Hall of Famer Coaltown. (You have to go back to the late 19th century to find the other sires coming up with the exacta: Longfellow had Riley over Bill Letcher in 1890, and in 1894, Falsetto had Chant over Pearl Song.)

Hall of Famer Curlin and Tapit, still seeking their first Derby victory, are the only sires with a shot at kicking off a double in Friday’s Kentucky Oaks (G1). (Young sire Laoban nearly had an Oaks and Derby runner in his very first crop, but Ava’s Grace will miss out on Friday after a setback.)

Curlin has multiple runners in both races. Like Into Mischief, he has a chance at an historic Derby exacta with Florida Derby hero Known Agenda and Lexington (G3) scorer King Fury. Curlin is even better positioned in the Oaks. He has three fillies in the line-up – unbeaten favorite Malathaat, another leading contender in Clairiere, and Millefeuille who’s capable of more. 

Tapit boasts the undefeated favorite in the Derby, Breeders’ Cup Juvenile (G1) champion Essential Quality. His lone Oaks hope, Pauline’s Pearl, enters on the upswing. (Note that Tapit’s son Frosted has a top Oaks threat in Travel Column.)

The last sire to celebrate an Oaks/Derby double (in the same year) is Hall of Famer Native Dancer, Curlin’s male-line ancestor, who sent out Native Street and Kauai King in 1966. According to pedigree maven Avalyn Hunter, the other three sires to achieve the feat are King Alfonso in 1885 (Lizzie Dwyer and Joe Cotton), McGee in 1918 (Viva America and the great gelding Exterminator), and Bull Lea in 1952 (Real Delight in the Oaks and Hill Gail in the Derby). 

Only 12 Kentucky Derby heroes have had sons emulate them by winning the roses, and none since Unbridled (1990) sired Grindstone (1996). Coming before that pair, Triple Crown sweeper Seattle Slew (1977) and Swale (1984) are the penultimate father-son combo. 

Orb, the 2013 Derby victor, hopes to update that stat with his son O Besos on Saturday. He’d be a fitting name to succeed Seattle Slew and Unbridled on the list since Orb descends from both, “Slew” on his sire’s side and Unbridled as his broodmare sire. 

If O Besos springs the upset, it would come a bit too late to prevent Orb’s export. He’s reportedly been sold to continue his stud career in Uruguay. 

The winners of the other two jewels of the Triple Crown in 2013 likewise have runners in the Derby. Preakness (G1) stealer Oxbow has Hot Rod Charlie, who’s out of a mare by Indian Charlie, third as the favorite in the 1998 Derby. Palace Malice, who flopped in the 2013 Derby but rebounded in the Belmont, is the sire of Like the King. 

Palace Malice, like Known Agenda and King Fury, is by the aforementioned Curlin, winner of the 2007 Preakness after placing third in the Derby. Fellow Preakness winner Bernardini (2006) is the sire of Bourbonic, who is also out of a mare by Afleet Alex, the 2005 Preakness and Belmont romper after his Derby third. 

Others with classic veterans as both sires and broodmare sires are Super Stock, by Dialed In (eighth as the 2011 Derby favorite) and out of a mare by 2005 Derby runner-up Closing Argument, and Brooklyn Strong, by Wicked Strong (fourth in the 2014 Derby and Belmont) and out of a mare by 2002 Belmont near-misser Medaglia d’Oro. 

Union Rags, the 2012 Belmont star after a belated seventh in the Derby, has Dynamic Strike. Four more Belmont winners factor as broodmare sires. 

Chief among them is Thunder Gulch, hero of both the Kentucky Derby and Belmont in 1995, and now the damsire of Helium. Empire Maker, the runner-up as the 2003 Derby favorite before prevailing in the Belmont, has sired the dams of both Rock Your World and Mandaloun. Victory Gallop, who famously nipped Real Quiet in the 1998 Belmont, is the broodmare sire of Keepmeinmind, while 1999 Belmont victor Lemon Drop Kid has the same relationship with Sainthood.

The aforementioned Tapit, ninth in the 2004 Derby, factors as both the sire of Essential Quality and the broodmare sire of Soup and Sandwich. Brilliant Speed, third in the 2011 Belmont, is the maternal grandsire of Medina Spirit. 

Zooming out for a longer-range look, the sire line of 1964 Kentucky Derby and Preakness champ Northern Dancer has the most representatives – eight in the 20-horse field. Four come courtesy of the Storm Cat branch, the Into Mischief trio (Highly Motivated, Mandaloun, and Soup and Sandwich) and Medina Spirit who’s by the Giant’s Causeway stallion Protonico. Brooklyn Strong descends from the Danzig branch, Hot Rod Charlie from Deputy Minister, Dynamic One from Dixieland Band, and Sainthood from the Eurocentric Sadler’s Wells. 

The Seattle Slew/A.P. Indy tribe fields five contenders – Essential Quality and Hidden Stash (by Tapit’s son Constitution), Super Stock, Bourbonic, and O Besos. 

Mr. Prospector’s dynasty also has a quintet. Smart Strike has three thanks to the influence of his son Curlin, while Fappiano is the ancestor of Rock Your World (by Candy Ride), and the Distorted Humor  stallion Ironicus got Helium in his first crop.

Indian Charlie, a scion of European import Caro (sire of 1988 Derby heroine Winning Colors), has put the sire line on a solid footing. His champion son Uncle Mo is now an emerging sire of sires, with Laoban a case in point for getting Keepmeinmind in his first crop.  

The Man o’ War sire line, looking for its first Derby score since Triple Crown legend War Admiral (1937), leans on Midnight Bourbon. His sire is Hall of Famer Tiznow, who came to hand too late to pursue the spring classics.

Hot Rod Charlie is a half-brother to champion sprinter Mitole, winner of the 2019 Metropolitan H. (G1) and Breeders’ Cup Sprint (G1). 

Midnight Bourbon is a half-brother to Girvin, hero of the Haskell (G1), Louisiana Derby (G2), and Risen Star in 2017, as well as Grade 3 scorers Cocked and Loaded and Pirate’s Punch.

Dynamic One is a grandson of champion Storm Flag Flying, who emulated her millionaire dam My Flag by winning the Breeders’ Cup Juvenile Fillies (G1) along with three other Grade 1s. My Flag, also third versus the boys in the 1996 Belmont, is in turn a daughter of unbeaten Hall of Famer Personal Ensign.

Essential Quality belongs to the celebrated line of blue hen *La Troienne. His dam, Grade 3-placed Delightful Quality, is a half-sister to champion Folklore, the ancestress of 2020 Japanese Triple Crown hero Contrail. Delightful Quality is also related to 2004 Derby and Preakness romper Smarty Jones. Hidden Stash likewise traces to *La Troienne, but via the branch of her family responsible for Hall of Famer Buckpasser, champion Outstandingly, noted sires Bernstein and Sky Mesa, and current star Maxfield (who runs in Friday's Alysheba [G2]). 

Two Derby contenders are out of Grade 1-winning mares. King Fury, as a $950,000 yearling the priciest entrant of those sold at auction, is out of 2016 Humana Distaff (G1) conqueror Taris. Known Agenda’s dam is 2013 Vanity H. (G1) vixen Byrama. 

Mandaloun was produced by Irish Group 2 scorer Brooch, who descends from the richly decorated family of Hall of Famer Equipoise. Bourbonic’s dam, Dancing Afleet, won the 2013 Delaware Oaks (G2) and traces to a full sister to Native Dancer. 

Rock Your World’s first three dams are all graded performers – multiple Grade 1-placed Charm the Maker, Grade 3 scorer Charm the Giant, and multiple Grade 2 queen Olympic Charmer. 

Medina Spirit sold for the cheapest price of all – $1,000 as a yearling (later $35,000 as a two-year-old) – but his further family is quite good. His maternal relatives include Grade 1 winner High Yield, Canadian Horse of the Year Catch a Glimpse, and Irish classic victress Forest Flower. 

Helium’s dam, Thundering Emilia, is a Group 3 winner and Group 1-placed member of an accomplished Peruvian family. 

Secretariat appears somewhere in the recesses of the pedigrees of nearly all the field (18 of 20). The 1973 Triple Crown conqueror endures through his daughters, and principally as the broodmare sire of such seminal influences as A.P. Indy, Storm Cat, and Gone West. 

Essential Quality, Medina Spirit, Soup and Sandwich, and Super Stock descend from all three, making for a Secretariat trifecta, so to speak, in their ancestry. The only two outliers lacking Secretariat are Known Agenda and Hot Rod Charlie.