Kentucky Derby pedigree profile: Tappan Street

A well-timed rally carried Tappan Street to victory in the 1 1/8-mile Florida Derby (G1) on the Road to the Kentucky Derby, stamping the bay colt as the latest top-tier Kentucky Derby (G1) contender sired by Into Mischief.

Into Mischief is in the midst of a stellar stud career. He’s ranked as North America’s leading sire by progeny earnings every year from 2019 through 2024, becoming the first to top the chart more than three times since Bold Ruler in the 1960s.

Along the way, Into Mischief has sired a spectacular list of champions and Grade 1 winners. Many of his best runners have been sprinters and milers like Breeders’ Cup Dirt Mile (G1) conquerors Life Is Good and Goldencents, Breeders’ Cup Filly & Mare Sprint (G1) winners Gamine and Covfefe, and Breeders’ Cup Juvenile Fillies (G1) victor Wonder Wheel.

But make no mistake, Into Mischief is also capable of siring classic winners. In 2020, his son Authentic wired the 1 1/4-mile Kentucky Derby and finished second in the 1 3/16-mile Preakness (G1) before winning the 1 1/4-mile Breeders’ Cup Classic (G1) to earn Horse of the Year honors. The following year, Into Mischief sired a second Kentucky Derby winner when Mandaloun claimed the roses via the disqualification of Medina Spirit.

In addition, Into Mischief is the sire of 2018 Kentucky Derby third-place finisher Audible, runaway Dubai World Cup (G1) hero Laurel River, and Santa Anita H. (G1) winner Newgate, all of whom have shown high-class form over 1 1/4 miles.

The record for most Kentucky Derby winners sired by a single stallion is three, held jointly by Virgil, Falsetto, Sir Gallahad III, and Bull Lea. Into Mischief has a strong chance to join this elite group in 2025. In addition to Tappan Street, Into Mischief’s contenders for this year’s Derby include Fountain of Youth (G2) winner and Florida Derby runner-up Sovereignty, champion two-year-old male Citizen Bull, and San Felipe (G2) runner-up Barnes.

In the case of Tappan Street, his Kentucky Derby credentials are further bolstered by his dam, Virginia Key, who brings some stamina to the genetic mix.

Virginia Key was a capable route racer. During her brief career, she won a one-mile and 40-yard maiden special weight and a one-mile allowance in addition to placing third (beaten only three-quarters of a length) in the 1 1/8-mile Gazelle (G2). Prior to Tappan Street, she foaled the stakes-placed Distorted d’Oro, a three-time winner over distances from about one mile to 1 1/16 miles.

Virginia Key, in turn, is a daughter of Distorted Humor out of the Newfoundland mare Our Khrysty. Newfoundland finished second by narrow margins in the Jockey Club Gold Cup (G1) and Suburban H. (G1) racing 1 1/4 miles, and he passed on his stamina to Our Khrysty, who scored her signature win in the 1 1/16-mile Turnback the Alarm H. (G3).

As for Distorted Humor, he’s enjoyed resounding success as both a sire and a broodmare sire. His sons and daughters including champion three-year-old male Funny Cide, a Kentucky Derby and Preakness winner who coincidentally defeated Newfoundland in the Jockey Club Gold Cup; Drosselmeyer, winner of the Breeders’ Cup Classic and 1 1/2-mile Belmont (G1); and Flower Alley, winner of the 1 1/4-mile Travers (G1) and the sire of Kentucky Derby/Preakness winner I’ll Have Another.

Meanwhile, daughters of Distorted Humor have foaled champion Arrogate, winner of the Breeders’ Cup Classic, Travers, and Dubai World Cup; Golden Sixty, victorious in a bevy of Group 1 prizes racing as far as 2,000 meters (about 1 1/4 miles) in Hong Kong; and the above-mentioned Breeders’ Cup Dirt Mile winner Life Is Good, who stretched his speed over 1 1/8 miles to win the Pegasus World Cup (G1).

The cross of Into Mischief with the Distorted Humor mare Virginia Key yields a high-class pedigree with potential for success over 1 1/4 miles. There’s a good chance Tappan Street will develop into Into Mischief’s record-equaling third Kentucky Derby winner.