Into Mischief Building a Kentucky Derby Legacy

This article initially appeared in the April issue of BloodHorse Magazine along with statistics by post position for the Kentucky Derby, and comprehensive racing statistics for trainers, jockeys, and sires at Churchill Downs. This section is available on BloodHorsePlus. The article below has been updated to include this year's Derby contenders. BloodHorse MarketWatch: Into Mischief Kentucky Derby Insights When Into Mischief retired to stud in 2009, few could have imagined he would become the first to sire back-to-back Kentucky Derby (G1) winners, while leading the North American general leading sires list for seven straight years. In the past century, only Bold Ruler has matched this leading sire streak, from 1963 to 1969. No other stallions are even close. One of the keys to Into Mischief's success can likely be attributed to the absence of Mr. Prospector in his pedigree. Raise a Native, the sire of Mr. Prospector, can be found on the damside of Into Mischief's sire Harlan's Holiday, but he comes through Exclusive Native and Affirmed, who is Harlan's Holiday's broodmare sire. In recent decades the blood of Mr. Prospector has become the mainstream of American bloodlines. Not only has he led the leading broodmare sire list nine times, but his male line flourishes through several of his top sons. Consequently, many of today's best racehorses and stallions show inbreeding or linebreeding to Mr. Prospector. This has created a kind of subspecies in the breed: stallions with multiple doses of Mr. Prospector in their pedigrees, and those such as Into Mischief who have none. Uncle Mo and Medaglia d'Oro are two other elite sires who may have benefited from their absence of Mr. Prospector blood. Into Mischief has indeed shown to be an ideal cross for the many broodmares loaded with Mr. Prospector, which include the dams of his three Kentucky Derby winners. Spendthrift Farm's marquee sire is now tied as the leading sire by number of Kentucky Derby winners, and has three chances this year to make Derby history by becoming the sole leading sire. Into Mischief was lightly raced with three wins from six starts, with his wins including the 2007 Futurity (G1) at Hollywood Park. He also was runner-up in the 2008 Malibu Stakes (G1) on his way to earning $597,080. Harlan's Holiday won three grade 1 stakes and earned a hefty $3.6 million and then went on to sire 95 stakes winners. Into Mischief's grandsire Harlan (by Storm Cat) also won a grade 1 in the 1994 Vosburgh Stakes (G1), but earned a more modest $403,174. Harlan died young after siring only 102 foals. Expectations for Into Mischief at stud were thus fairly modest, as he entered stud at $12,500 in 2009 and would be priced at $7,500 three years later. But his first crop of 42 foals produced 37 runners (88%), 29 winners (69%), and seven black-type winners (17%). This crop included Goldencents, who won the 2013 Breeders' Cup Dirt Mile (G1) at 3, and again at 4. Into Mischief rose up the stallion ranks as he attracted more, higher-quality mares, breaking into the top 12 leading sires in 2017 and capturing his first leading sire title in 2019. He made history with his eighth and ninth crops, which included consecutive Kentucky Derby winners Authentic and Mandaloun, respectively. Authentic went on to win the 2020 Breeders' Cup Classic (G1) at 3 in gate-to-wire fashion in a track record of 1:59.60 at Keeneland. His performances earned him Eclipse Awards for champion 3-year-old male as well as Horse of the Year. For the season, he won five of seven starts, good for $7.17 million. Authentic hails from a surprisingly modest female family. His second and third dams produced no stakes winners from their 18 foals. His dam Flawless won one of only two starts and $40,600, and she has not produced any other stakes winners from her other nine foals of racing age. But her sire, Mr. Greeley, may hold the key. He's a grandson of Mr. Prospector and inbred 4x3 to Bold Ruler and 4x4 to Native Dancer. These two bloodlines have crossed extremely well throughout history, including the golden cross of A.P. Indy x Mr. Prospector (Mineshaft, Malibu Moon, Flatter, Pulpit, etc.). So Authentic shows linebreeding to Bold Ruler and Native Dancer both top and bottom in his pedigree. Mandaloun gave Into Mischief his second Derby winner in 2021. Albeit a win via disqualification, Mandaloun gave a valiant performance and just missed at the wire by half a length. Unlike Authentic, he comes from a strong female family. His dam Brooch (by Empire Maker) was a group 2 winner of $217,059. Furthermore she is inbred 4x4 to Mr. Prospector, a key ingredient in the mates of Into Mischief. Second dam Daring Diva (by Dansili) was a stakes winner in France who produced two stakes winners and a group 3-placed winner, while third dam Aspiring Diva (by Distant View) was stakes-placed in France and produced three stakes winners. Once again, this family is loaded with Native Dancer blood and shows 11 generations of stakes winners. In addition to his Kentucky Derby, Mandaloun won the Haskell Stakes (G1) also by disqualification, but again missed even more narrowly by a nose at the wire. He has other outright wins in the 2021 Risen Star Stakes (G2) and 2022 Louisiana Stakes (G3) for career totals of seven wins in 12 starts and $3,356,052. In 2025, Sovereignty gave Into Mischief his third Derby winner in the past six years and was named Horse of the Year and champion 3-year-old male. In addition to the Kentucky Derby, he won the Belmont Stakes (G1), Travers Stakes (G1), and the Jim Dandy Stakes (G2), and has returned to racing this year, finishing second in the April 18 Oaklawn Handicap (G2) in his first start since the Aug. 23 Travers. His dam Crowned (by Bernardini) was unraced, and Sovereignty is her first stakes winner from three foals to race. However, she is inbred 3x4 to Seattle Slew, 4x4 to Fappiano, and 5x5x4 to Mr. Prospector (the sire of Fappiano). Second dam, Mushka (by Empire Maker), was a grade 1 winner of $1,096,125, and is inbred 4x3 to Mr. Prospector, but produced no stakes winners from five foals. Third dam Sluice (by Seeking the Gold), was a minor stakes winner of $202,453, but produced only one stakes winner from 12 foals. Fourth dam Lakeway (by Seattle Slew) was a four-time grade 1 winner of $965,330, but produced only one stakes winner from her 14 foals. Sovereignty shows three stakes winners from his first four dams, but they produced those stakes winners from 34 foals. Into Mischief's three Kentucky Derby starters this year are morning-line favorite Renegade, Commandment, and Potente. Renegade, who won the Arkansas Derby (G1) by 4 lengths, is out of the Curlin mare and grade 3 winner Spice Is Nice, who is a daughter of grade 1 winner Dame Dorothy. This colt is Curlin's first representative in the Kentucky Derby as a broodmare sire. Renegade is not inbred, but Spice Is Nice is inbred 3x4 to Mr. Prospector. Commandment won the Florida Derby (G1) and the Fountain of Youth Stakes (G2). He is out of grade 1 winner Sippican Harbor, who is a daughter of 2013 Kentucky Derby winner Orb. Commandment is also not inbred through the first five generations, but Orb is inbred 3x4 to Mr. Prospector and 5x5 to Bold Ruler. Potente, who was runner-up to So Happy in the Santa Anita Derby (G1), is out of the Awesome Again stakes-placed winner Sweet Sting. The mare is a daughter of 2000 champion grass mare and multiple stakes producer Perfect Sting (Red Ransom). Potente's only inbreeding is 5x5 to Hail to Reason. He does have one line of Mr. Prospector in his pedigree as the broodmare sire of Awesome Again's dam Primal Force. Sweet Sting is inbred 5x5 to Nearctic through his son Northern Dancer, who is the great-grandsire of Awesome Again, and through Christmas Wind, the second dam of Perfect Sting's sire Red Ransom. Another Kentucky Derby starter with ties to Into Mischief is Robert B. Lewis Stakes (G3) runner-up Intrepido, who is by Into Mischief's son Maximus Mischief. Intrepido is out of the Pleasantly Perfect daughter Overly Indulgent, who is inbred 3x5 to Mr. Prospector and 4x5 to Raise a Native, the sire of Mr. Prospector. Raise a Native in the fifth generation carries on through his son Exclusive Native, the sire of 1978 Triple Crown winner Affirmed. This makes Intrepido inbred 5x4 to Affirmed, the broodmare sire of Harlan's Holiday. BloodHorse bloodstock editor Eric Mitchell contributed to this article.