10 Pedigree fun facts: Timberlake

Mar 12, 2024 Kellie Reilly/Brisnet.com

Timberlake could become a record-equaling third Kentucky Derby (G1) winner sired by Into Mischief, and that’s just the starting point to explore his classically-oriented pedigree.

Both of Timberlake’s grandsires have become part of Derby history, first as beaten favorites, and then as stallions with Derby-winning descendants. Moreover, his pedigree expands beyond the U.S. Triple Crown scene to include premier European classic influences.

Here are 10 pedigree fun facts:

1. Into Mischief aims to tie the record of siring three Derby winners.

The perennial leading sire in North America, Into Mischief is the only stallion to sire back-to-back Derby winners in Authentic (2020) and Mandaloun (2021). But he can enhance his historical legacy further by coming up with a third Derby hero, a feat that would put him in very rare company.

The last stallion to sire three Derby winners was Calumet Farm’s great patriarch Bull Lea, who furnished Triple Crown legend Citation (1948), Hill Gail (1952), and Iron Liege (1957). Bull Lea is only the fourth member of that sires’ club, joining 19th-century stalwarts Virgil and Falsetto as well as *Sir Gallahad III, sire of Triple Crown star Gallant Fox (1930), Gallahadion (1940), and Hoop Jr. (1945).

Into Mischief has another notable son on the trail in Resilience, who was fourth in the Risen Star (G2). Even more prominent are Into Mischief’s grandsons Mystik Dan, Domestic Product, and Track Phantom (on his mother’s side).

2. Into Mischief was never worse than second in his racing career.

With his prolific record at stud, siring champions running the gamut from Horse of the Year Authentic and Kentucky Oaks (G1) heroine Pretty Mischievous to brilliant sprinters like Covfefe, and $4.5 million-earner Life Is Good, it’s easy to forget how good Into Mischief was on the racetrack himself.

Trained by Hall of Famer Richard Mandella, Into Mischief won three of six starts and placed second in the others. He scored his signature win in the 2007 CashCall Futurity (G1) at old Hollywood Park, stamping himself as an exciting Derby hopeful. After a runner-up effort in the 2008 San Vicente (G2), however, he was sidelined by injury. Into Mischief didn’t return until the fall of his sophomore season. Capturing his comeback in the Damascus S. at Santa Anita, he was second in the Malibu (G1) over the same track and seven-furlong trip, and retired to stud.

3. Grandsire Harlan’s Holiday was unplaced as the 2002 Derby favorite.

Into Mischief is by the Storm Cat-line stallion Harlan’s Holiday, who was out of a mare by 1978 Triple Crown sweeper Affirmed. Harlan’s Holiday was the lukewarm favorite in the 2002 Kentucky Derby after daylight victories in the Florida Derby (G1) and Blue Grass (G1), but he wound up seventh behind front-running War Emblem at Churchill Downs. In 2003, Harlan’s Holiday went on to win the Donn H. (G1) and took second in both the Dubai World Cup (G1) and Hollywood Gold Cup (G1).

While Into Mischief is his most significant bequest, Harlan’s Holiday also sired 2012 Breeders’ Cup Juvenile (G1) champion Shanghai Bobby; once-beaten sprint celebrity Majesticperfection; Canadian classic winner Ami’s Holiday; Conquest Harlanate, a champion in Canada; and millionaires Good Samaritan, Mendip, and Willcox Inn, not even to mention his major winners in Argentina.

4. Into Mischief is a half-brother to Beholder and Mendelssohn.

Into Mischief’s dam (mother), Leslie’s Lady, was a minor stakes winner at Hoosier Park who became one of the most celebrated matrons of the modern era. She produced two high-profile performers after Into Mischief: four-time Eclipse Award champion Beholder and fellow Breeders’ Cup victor Mendelssohn, who won on three continents.

Beholder was enshrined in the Hall of Fame in recognition of her extraordinary resume. Thrice successful at the Breeders’ Cup – the 2012 Juvenile Fillies (G1) and two editions of the Distaff (G1) (2013 and 2016), the Mandella trainee also crushed males in the 2015 Pacific Classic (G1). Beholder bankrolled more than $6.1 million from a record of 18 wins and six seconds in 26 starts, including 11 Grade 1 trophies. She’s now a Grade 1 producer herself, as daughter Tamara dominated last summer’s Del Mar Debutante (G1).

Mendelssohn was a globetrotter for Irish maestro Aidan O’Brien. The hero of the 2017 Breeders’ Cup Juvenile Turf (G1), Mendelssohn routed the 2018 UAE Derby (G2) in track-record time in his dirt debut. He couldn’t replicate that performance in the Kentucky Derby, where he was badly hampered early and never recovered on a sloppy track. Mendelssohn was able to fare better when placing in the Travers (G1) and Jockey Club Gold Cup (G1).

5. Timberlake’s maternal grandsire, Lookin at Lucky, was unlucky in the 2010 Derby.

Lookin at Lucky was the first colt in 30 years to be voted champion at two and three, ending a drought dating back to the great Spectacular Bid. But unlike “The Bid,” Lookin at Lucky was unlucky in the Kentucky Derby, rallying for sixth after getting clobbered from his rail post. Lookin at Lucky set the record straight with a cleaner trip in the Preakness (G1) and confirmed his status as the best of his crop in the Haskell (G1).

As a sire, Lookin at Lucky gained Derby compensation through his son Country House, who was awarded the victory via disqualification in 2019. Another son, Lookin at Lee, was runner-up in the 2017 Derby. Lookin at Lucky’s leading performer is champion Accelerate, who crowned his 2018 campaign in the Breeders’ Cup Classic (G1).

Lookin at Lucky is represented on the 2024 trail by Lucky Jeremy, and he also factors as the maternal grandsire of Derby hopeful Time for Truth. Before Timberlake came along, the most famous runner out of a Lookin at Lucky mare was Gronkowski, runner-up in Justify’s Belmont (G1) and the near-misser in the 2019 Dubai World Cup.

6. Timberlake’s mother and uncle were stamina-laden runners in England.

Timberlake’s dam, Irish-bred Pin Up, required long distances during her racing career in England. She broke her maiden going 1 1/2 miles at Ripon, in her seventh attempt for trainer Richard Fahey.

A step up to 1 3/4 miles helped Pin Up achieve her two highest-rated efforts. Up in time to win a Class 2 handicap at Haydock, where she was among the lighter weights, Pin Up earned valuable black-type as the third-placer in the 2015 Noel Murless S. at Ascot.

Pin Up’s half-brother, Thomas Chippendale, won majors for two straight summers at Royal Ascot. After taking the 2012 King Edward VII (G2), he added the 2013 Hardwicke (G2) over the same 1 1/2-mile trip.

7. Timberlake’s blueblood grandmother placed in classics.

Pin Up inherited her staying capacity from her own dam, All My Loving, who collected a series of placings in marquee events. Third in the 2007 Oaks (G1) at Epsom and in the Irish Oaks (G1), All My Loving was also runner-up in the Ribblesdale (G2) at Royal Ascot. She came closest to a stakes breakthrough in the Park Hill (G2) over more than 1 3/4 miles at Doncaster, where she was denied by a neck.

All My Loving was one of a trio of classic-performing full sisters, all trained by O’Brien at Ballydoyle. Quarter Moon and Yesterday were both second in the Oaks at Epsom. Quarter Moon, Ireland’s champion two-year-old filly of 2001, placed in a pair of Irish classics as well. Yesterday, the winner of the 2003 Irish 1000 Guineas (G1), took minor awards in three other top-level events, including the Breeders’ Cup Filly & Mare Turf (G1).

8. All My Loving is bred on the Sadler’s Wells/Darshaan cross.

All My Loving, Quarter Moon, and Yesterday are all by supersire Sadler’s Wells and out of Jude (hence the allusions to Beatles songs).

Sadler’s Wells, a son of 1964 Derby champion Northern Dancer, has carved out his own branch of the sire line. Sire of the great Galileo and Montjeu, Sadler’s Wells also has an American presence via El Prado, sire of champion Kitten’s Joy and Medaglia d’Oro.

Yet daughters of Sadler’s Wells have been no less a potent vector of his influence. Sadler’s Wells mares have produced such European standouts as Enable, Workforce, and Sakhee, all winners of the Prix de l’Arc de Triomphe (G1); Japanese champion and prolific broodmare Cesario; and 2019 Preakness scorer War of Will, to give just a tiny sampling.

Sadler’s Wells counts six Breeders’ Cup wins as a sire, led by his two-time Turf (G1) star High Chaparral, who turned the Epsom/Irish Derby (G1) double in 2002. Both High Chaparral and Islington, the 2003 Filly & Mare Turf victress by Sadler’s Wells, are out of mares by French champion Darshaan.

Other standouts bred on the Sadler’s Wells/Darshaan cross are 2001 St Leger (G1) hero Milan, runner-up in the Breeders’ Cup Turf; star stayers Septimus and Ebadiyla; and 2011 Epsom Derby scorer Pour Moi (by Montjeu).

9. Darshaan beat Sadler’s Wells in the 1984 French Derby.

It’s a nifty development that Sadler’s Wells crossed so well with Darshaan, since the two met in the 1984 French Derby. Darshaan’s superior stamina carried the day in the about 1 1/2-mile classic, relegating Sadler’s Wells to an honorable second. Sadler’s Wells excelled in the mile to 10-furlong range, with sparkling wins in the Irish 2000 Guineas (G1), Eclipse (G1), and Phoenix (now Irish) Champion (G1).

Darshaan was a successful sire in his own right. His Breeders’ Cup Turf-winning son Kotashaan reigned as U.S. Horse of the Year in 1993; Mark of Esteem was a champion miler in England; and Dalakhani, who emulated Darshaan in the French Derby, added the prestigious Arc. Dalakhani went on to sire two-time Turf champ Conduit, whose dam is by – can you guess? – Sadler’s Wells.

10. Timberlake hails from an all-star family tracing to the “Flying Filly.”

Timberlake’s aforementioned great-grandmother (third dam), Jude, is herself out of the outstanding broodmare Alruccaba, ancestress of a host of major winners. Kirsten Rausing’s Lanwades Stud is most associated with the cultivation of this superb “A” family.

European champion Alpinista, the 2022 Arc heroine, descends from Jude’s sister Alouette. Alpinista and current highweight stayer Eldar Eldarov both count Anglo-German champion Albanova as their grandmother; Albanova is in turn a full sister to two-time Champion (G1) victress Alborada.

Jude’s multiple Group 2-winning half-sister Last Second foaled Aussie Rules, winner of a French mile classic as well as the 2006 Shadwell Turf Mile (G1) at Keeneland, and Last Second also factors as the granddam of multiple Group 1 scorer Coronet. Another of Jude’s half-sisters, Alleluia, upset older males in the historic Doncaster Cup (G3) in 2001, and went on to produce champion staying mare Allegretto.

The all-star female line traces back to Mumtaz Mahal, the “Flying Filly” who was England’s top two-year-old of 1923 and a dazzling sprinter at three. A treasured influence in the Aga Khan’s breeding program, Mumtaz Mahal is the ancestress of all-time greats Petite Etoile and Zarkava, as well as Shergar, *Migoli, and such key sires as *Nasrullah, *Royal Charger, and *Mahmoud.