Into Mischief has already firmly written himself into the history of the American stallion ranks, with his six consecutive sire titles the most in more than a half-century. Now, he is looking to write another chapter as the first stallion since the 1950s to sire three Kentucky Derby winners, which would tie him for the all-time record. Standing at Spendthrift Farm, Into Mischief sired his first classic winner when eventual Horse of the Year Authentic took the pandemic-delayed 2020 Derby. The following spring, Into Mischief’s son Mandaloun crossed the line second by a half-length to Medina Spirit but was later elevated to first due to Medina Spirit’s disqualification for a medication violation. Into Mischef’s representatives in this year’s Kentucky Derby are Eclipse Award champion 2-year-old male Citizen Bull and Florida Derby runner-up Sovereignty. The other stallions to sire three Kentucky Derby winners are Virgil, with Vagrant (1876), Hindoo (1881), and Ben Ali (1886); Falsetto, with Chant (1894), His Eminence (1901), and Sir Huon (1906); Sir Gallahad III, with Triple Crown winner Gallant Fox (1930), Gallahadion (1940), and Hoop Jr. (1945); and Bull Lea, with Triple Crown winner Citation (1948), Hill Gail (1952), and Iron Liege (1957). Into Mischief’s sixth leading sire title in 2024 marked the most consecutive titles for a North American stallion since the great Bold Ruler led the list for seven straight years, from 1963-69. Bold Ruler claimed an eighth title posthumously in 1973, the year his son Secretariat dominated the Triple Crown. Bold Ruler is tied with the pre-Civil War stallion Glencoe for the second-most North American sire titles all-time, trailing only the great Lexington, whose career spanned the Civil War while he rolled to an incredible 16 titles. :: DRF Kentucky Derby Package: Save on PPs, Clocker Reports, Betting Strategies, and more.