Withers (G3) hero Risk Taking has a well-constructed pedigree, a rock-solid foundation to assure even the most conservative investor. Bred along a successful cross, he also sports a less common inbreeding pattern, one that he shares with a commanding Kentucky Derby (G1) winner of recent years. 

Risk Taking descends from the sire line of Northern Dancer, the 1964 Kentucky Derby and Preakness (G1) champion, but via his son Sadler’s Wells, whose branch has had a profound impact in Europe. Sadler’s Wells carved out his own legacy as a supersire through such outstanding sons as Galileo and Montjeu. 
Another of Sadler’s Wells’ offspring, El Prado, extended his influence stateside. An Irish champion juvenile, El Prado proved well suited to American conditions. He sired turf champion Kitten’s Joy and 2005 Breeders’ Cup Mile (G1) winner Artie Schiller, but also classy dirt performers. Chief among them was Medaglia d’Oro, sire of Risk Taking.
Medaglia d’Oro competed in all three jewels of the 2002 Triple Crown, finishing fourth in the Kentucky Derby, regressing to eighth in the Preakness, but saving his best for last when a close second in the Belmont (G1). He continued his progress through the summer by turning the Jim Dandy (G2)/Travers (G1) double. Placed in back-to-back runnings of the Breeders’ Cup Classic (G1), Medaglia d’Oro added the 2003 Whitney (G1) and 2004 Donn (G1) to his ledger. 

In his very first season at stud, Medaglia d’Oro sired a Hall of Famer in Rachel Alexandra. During her Horse of the Year campaign in 2009, she scored historic wins over males in the Preakness, Haskell Invitational (G1), and Woodward (G1), as well as conquering the Kentucky Oaks (G1) by a record 20 1/4 lengths. 

Medaglia d’Oro’s other standouts include two-time Eclipse champion filly Songbird; Canadian Horse of the Year Wonder Gadot, who beat the boys in the 2018 Queen’s Plate; 2017 Breeders’ Cup Turf (G1) winner Talismanic; Vancouver, hero of Australia’s rich Golden Slipper (G1) for juveniles in 2015; Violence, a leading hopeful on the 2013 Kentucky Derby trail before a career-ending injury; and current Hong Kong phenom Golden Sixty, who just extended his winning streak to 13.
Rachel Alexandra, Songbird, and Golden Sixty are bred along similar lines, all being out of mares descending from Forty Niner, a champion son of Mr. Prospector. That is the heady genetic mix behind Risk Taking as well. Risk Taking’s dam is by the Forty Niner stallion Distorted Humor – the same cross responsible for Golden Sixty and multiple U.S. Grade 1 stars Elate and New Money Honey. 
Distorted Humor has been a force in American classic pedigrees. Siring 2003 Derby and Preakness champion Funny Cide in his first crop, he also got Drosselmeyer, the 2010 Belmont and 2011 Breeders’ Cup Classic winner, and 2005 Travers star Flower Alley, himself the sire of 2012 Derby and Preakness champ I’ll Have Another.
As a broodmare sire, Distorted Humor’s influence goes well beyond the link with Medaglia d’Oro. His daughters have produced the likes of Arrogate, Constitution (sire of last year’s Belmont romper Tiz the Law), and early 2021 Derby favorite Life Is Good, all from different sire lines. 
Risk Taking is out of Run a Risk, twice stakes-placed on turf. Her most accomplished half-brothers, Grade 3 winners Rey de Cafe and El Crespo, were also turf campaigners.

Run a Risk is out of a mare by regally bred Private Account, son of Hall of Famer Damascus (the 1967 Preakness and Belmont winner). Because Medaglia d’Oro is out of a Damascus-line mare as well, Risk Taking is inbred to Damascus. 

Interestingly, so was Big Brown, the imperious winner of the 2008 Derby and Preakness. Damascus factored on the dam’s side of both of Big Brown’s parents, a position similar to that visible in Risk Taking. The difference is that Risk Taking’s strains of Damascus come from two of his sons, while Big Brown descends from daughters of Damascus.
Run a Risk’s dam, Commodities, was the product of bluebloods from the collection of patrician owner/breeder Ogden Phipps. Her sire, the aforementioned Private Account, is best known for siring unbeaten Hall of Famer Personal Ensign, mud-spattered but up in time in the epic 1988 Breeders’ Cup Distaff (G1). Commodities is out of Tricky Game – herself by another Phipps celebrity, Majestic Light (a son of 1969 Derby and Preakness winner Majestic Prince). 
Commodities’ pedigree sports close inbreeding to all-time Phipps great Buckpasser, twice appearing in his pivotal role as a broodmare sire. Buckpasser sired Private Account’s dam, champion Numbered Account, and Tricky Game’s dam, Con Game, who also produced Seeking the Gold.
Con Game is in turn a half-sister to champion Queen of the Stage and to Reviewer, forever to be remembered as the sire of the brilliant but ill-fated Ruffian. Reviewer, Queen of the Stage, and Risk Taking’s ancestress Con Game are all out of Broadway, a mare by 1954 Preakness hero Hasty Road.
Broadway’s dam, Flitabout, was runner-up in the 1948 Coaching Club American Oaks. Bred by the legendary Col. E.R. Bradley’s Idle Hour Stock Farm, Flitabout was by Maryland legend Challedon, winner of the 1939 Preakness.
Following the matrilineal trail back further, Risk Taking belongs to the family labeled 5-c, tracing to Chanoinesse, a full sister to Hermit. The 1867 Epsom Derby winner, Hermit was so influential as a sire that he became a building block of Thoroughbred pedigrees.