The thriving commercial enterprise that we might call “Into Mischief & Sons” grows bigger and better and more impressive by the year.
In 2025, the founder of this racing dynasty, Into Mischief (by Harlan’s Holiday), led the national sire list for the seventh time in a row, tying the mark of the legendary Bold Ruler (Nasrullah), who also led the list an eighth time (posthumously) when Secretariat won the Triple Crown in 1973.
Also in 2025, Into Mischief’s son Sovereignty won the Grade 1 Kentucky Derby, Belmont Stakes, and Travers, and the colt was elected both champion 3-year-old colt and Horse of the Year. The Derby victory moved Into Mischief into a tie among sires of Kentucky Derby winners.
None has more than three winners. So far.
In 2026, Into Mischief leads all sires at the Kentucky Derby with three entered to start for the classic Run for the Roses on May 2. Among that trio is the early favorite for the race, Renegade, who won the G1 Arkansas Derby; Commandment, who won the G1 Florida Derby; and Potente, who was second in the G1 Santa Anita Derby.
Contrary to previous years, however, Into Mischief currently is not in the lead among all sires on the general sire list. Instead, that role is held by his younger rival Not This Time (Giant’s Causeway), at least for the time being. Not This Time is represented at the Kentucky Derby by Six Speed, winner this year of three races in a row over the winter in the United Arab Emirates, including the G3 UAE 2,000 Guineas, and second in the G2 UAE Derby to fellow Derby entrant Wonder Dean (Dee Majesty).
The next two stallions on the leading sires list – Nyquist (Uncle Mo) and Gun Runner (Candy Ride) – both have colts in the Derby this Saturday, as well. Litmus Test (Nyquist) won the G2 Los Alamitos Futurity last season but in his last start was unplaced in the Arkansas Derby. In contrast, Gun Runner has a hot pistol with Further Ado, who won the G2 Kentucky Jockey Club Stakes last year at Churchill Downs and most recently won the G1 Blue Grass Stakes at Keeneland in early April.
These and 15 other colts will try to keep the Into Mischief Express from pulling into the winner’s circle at Churchill Downs after the Derby. History, at least, is on their side.
Two stallions, Virgil and Falsetto, sired a trio of Kentucky Derby winners in the late 19th and early 20th centuries. Only two more stallions joined this select company through the remainder of the 20th century. These were Clairborne Farm’s legendary Sir Gallahad III (Teddy) and the great light of Calumet Farm’s glory days, Bull Lea (Bull Dog).
Sir Gallahad got his first home run over the fence with his first American crop. In that group was a striking bay named Gallant Fox, who not only won the Derby but also the 1930 Triple Crown. The sire’s two further Kentucky Derby winners were Gallahadion (1940) and Hoop Jr. (1945).
Bull Lea’s first Kentucky Derby winner came in his fifth crop, but Citation, like Gallant Fox, was not an ordinary Derby winner. Citation won the 1948 Triple Crown, became racing’s first $1 million winner, and is one of the horses mentioned in every discussion of the greatest of the great racers of the past. Bull Lea’s next two Derby winners were Hill Gail (1952) and Iron Liege (1957).
In one further point of interest, Bull Dog, the sire of Bull Lea, and Sir Gallahad were full brothers: both by Teddy out of the fabulous broodmare Plucky Liege (Spearmint). At one point, it seemed not a question of whether Teddy’s male line would take over American racing but only to what extent it would smother all others. Today, it is essentially extinct.
Among other stallions at this level in the sport, some did not score multiples in siring Kentucky Derby winners. Bold Ruler sired only a single Kentucky Derby winner, Secretariat (1973), like Mr. Prospector, Fusaichi Pegasus (2000).
And if you want to win the pot at your Kentucky Derby party, stump the others by asking how many Kentucky Derby winners were sired by Storm Cat: Zero.
Storm Cat’s descendants, however, are trying to corner the Derby market. Not This Time is a grandson of the multiple leading sire, and Into Mischief is a great-grandson of the Overbrook Farm legend.
If Into Mischief gets a fourth Kentucky Derby winner, he will move into a category all his own.
Published on the Paulick Report website – Paulickreport.com
