Timberlake Colt by Into Mischief – Pin Up, by Lookin At Lucky Bred in Kentucky by St. Elias Stables ($350,000 Keeneland September yearling purchase by Maverick Racing and Siena Farm) Into Mischief’s five consecutive leading sire titles have placed his name among some of the all-time great American sires. As the 150th Kentucky Derby approaches, he is eyeing another historic accomplishment. Authentic’s 2020 Derby victory, followed by Mandaloun’s promotion by disqualification in 2021, makes Into Mischief officially the first stallion ever to sire back-to-back Derby winners. Another victory will tie him for the most wins in the classic all-time with Virgil, Falsetto, Sir Gallahad III, and Bull Lea. Into Mischief’s top prospect to emerge thus far is Derby Watch member Timberlake. The winner of the Grade 1 Champagne makes his 3-year-old debut in Saturday’s Grade 2 Rebel at Oaklawn Park. :: KENTUCKY DERBY 2024: Derby Watch, point standings, prep schedule, news, and more Into Mischief sired back-to-back Breeders’ Cup Filly and Mare Sprint winners and divisional Eclipse champions in Covfefe (2019) and Gamine (2020). Authentic, who won the pandemic-delayed Derby, finished second in the Preakness, and won the Breeders’ Cup Classic to earn Horse of the Year honors, was considered a breakthrough horse. However, Into Mischief had been knocking at the door in the classics prior to that. Audible won the 2018 Florida Derby before finishing third to champions Justify and Good Magic in the Kentucky Derby. The following year, Owendale was third in the Preakness Stakes. Irish-born Pin Up hails from a long-winded turf family. The stakes-placed mare scored her two wins at 12 furlongs and 14 furlongs. Along with Timberlake, who has not yet run beyond 1 1/16 miles, she is the dam of Al Qaqaa, a winner at 12 furlongs, and Page Three, a winner at 11 furlongs. Second dam All My Loving won at 1 1/4 miles and was multiple Group 1-placed at 12 furlongs, including third-place finishes in the Epsom Oaks and Irish Oaks. That mare is also the dam of Thomas Chippendale, a multiple Group 2 winner at 12 furlongs. All My Loving is a full sister to Group 1 winners Yesterday and Quarter Moon. Yesterday won the Irish 1000 Guineas at a mile, but was second by a neck in the Epsom Oaks. Quarter Moon took the Moyglare Stud at seven furlongs, but was second in both the Epsom Oaks and Irish Oaks. Quarter Moon is the dam of Diamondsandrubies, winner of the Group 1 Pretty Polly at 10 furlongs. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.