Highly Motivated earned his shot at the 2021 Kentucky Derby with a third-place finish in the Gotham Stakes (G3) at Aqueduct and a narrow second-place defeat in the Blue Grass Stakes (G2) at Keeneland.

Ultimately, Highly Motivated finished 10th in the Kentucky Derby after collecting 50 qualifying points and finishing in 11th place on the Road to the Kentucky Derby leaderboard. The Chad Brown trainee has two wins, two seconds and one third in six starts, with current earnings of $320,050.

2021 Road to the Kentucky Derby

In his second start of the year, Highly Motivated gave two-year-old champion Essential Quality all he could handle in the Blue Grass Stakes (G1) at Keeneland.

From the outset, Highly Motivated set the pace under jockey Javier Castellano, shadowed by Essential Quality and jockey Luis Saez. The contest evolved into a match race, and the colts separated themselves from the rest of the field by a widening five lengths. Essential Quality showed his class by inching clear of the gutsy Highly Motivated near the wire to win by a neck. The final time for nine furlongs was 1:48.50.

Highly Motivated had a rough beginning to his three-year-old season. He bobbled at the start of the one-mile Gotham Stakes and was stuck near the back of the eight-horse pack. He was bothered twice and had to steady, losing about a length in the process. Castellano took the colt to the outside for running room and advanced four-wide around the turn. They passed tired horses to finish a clear third.

Career beginnings

In his six-furlong debut at Saratoga on August 29, Highly Motivated developed the trait that causes him trouble in most races. He was off slow at the break of the Maiden Special Weight contest and bumped with a rival. He then wove through traffic and went wide around the turn. He battled with the pacesetter and put that one away but couldn't hold off the late charge of the winner, Founder, having to settle for second-place by a neck.

The following month, Highly Motivated graduated at Belmont Park in a six-and-a-half furlong Maiden Special Weight event.

This time, he veered in at the start, which caused a chain reaction with four others, causing them to steady and stumble. Javier Castellano handled the colt patiently, weaving through traffic. They split foes in the stretch, Highly Motivated inching clear to win by one-and-three-quarter lengths over Known Agenda. That horse returned to win the Florida Derby as a three-year-old and is one of the leading contenders for the Kentucky Derby.

Highly Motivated stepped up in the Nyquist Stakes at Keeneland on the Breeders' Cup undercard in his two-year-old finale.

Once again, Highly Motivated broke inwards. He tracked the pace from mid-pack on the inside during the race's early stages. Castellano tipped the colt three-wide at the quarter-pole. The pair swept by the dueling pacesetters to triumph by a widening four-and-a-quarter lengths in the six-and-a-half furlong race.

Highly Motivated's connections

Trainer Chad Brown worked as an assistant to the legendary Bobby Frankel for six years. He started his own stable with only 10 horses in 2007.

Brown quickly rose in the trainer ranks and has earned the Eclipse Award for Outstanding Trainer for four consecutive years, from 2016 through 2019. He has over $200million in career earnings.

Before the 2021 race, Chad Brown had sent five contenders to the Kentucky Derby since 2013. Good Magic finished second in 2018, his best achievement thus far.

Javier Castellano started his riding career in Venezuela in 1996. The following year, he moved his tack to South Florida and became a popular rider. In 2001, Castellano left the sunny climes for the New York racing circuit and his career took off. He paired with the 2004 Horse of the Year Ghostzapper and guided Bernardini to three Grade One victories in 2006, including the Preakness Stakes.

Castellano earned Eclipse Awards for Outstanding Jockey from 2013 to 2016 inclusive and was inducted into the Hall of Fame in 2017.

The experienced journeyman has now ridden in 15 Kentucky Derbies but has never won. His best effort was a third-place finish with Audible in 2018.

However, Castellano has won the Preakness twice (2006 and 2017) and has placed second in three Belmont Stakes (2011, 2014 and 2016).

Living just three blocks from Pimlico Race Course, Seth Klarman became an avid horse racing fan from an early age. In 1993, he formed Klaravich Stables with a friend, and the pair campaigned many graded winners.

These included Preakness Stakes victor Cloud Computing, who was conditioned by Brown and ridden by Castellano in 2017. The horse was owned in partnership with William Lawrence.

Klaravich Stables and William Lawrence also owned 2019 Horse of the Year Bricks and Mortar. Klaravich and Lawrence were given the Eclipse Award Leading Owner gong in the same year.

Highly Motivated's pedigree

Highly Motivated (Into Mischief - Strong Incentive by Warrior's Reward) has the pedigree to handle nine furlongs, but 10 furlongs could be farther than he wants to travel.

Into Mischief, a son of Harlan's Holiday, never finished worse than second in six career starts. He won the CashCall Futurity (G1) (now known as the American Pharoah Stakes) and the listed Damascus Stakes while placing in the Malibu (G1), San Vicente (G2), and Hollywood Prevue (G3). Into Mischief was successful from six-and-a-half furlongs to a mile-and-a-sixteenth (eight-and-a-half furlongs).

Into Mischief is a leading North American sire, with six champions and almost 40 Grade One winners. However, his offspring have distance limitations.

Only three of his stakes winners have been successful at 10 furlongs, including 2020 Kentucky Derby (G1) winner Authentic. Highly Motivated, Soup and Sandwich, and Mandaloun are Into Mischief's 2021 Kentucky Derby representees.

Highly Motivated is the first stakes winner in his immediate family. His dam Strong Incentive was slow to mature but won the seven-furlong Jammed Lovely Stakes at Woodbine in her final race, the last of six career starts.

The second generation of Highly Motivated female family is sprint-oriented. His dam's half-brother Hall Pass is stakes-placed and Highly Motivated's second dam G G's Dolly is a minor stakes-winning sprinter.

Highly Motivated

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Chad Brown's Highly Motivated finished 10th in the 2021 Kentucky Derby after a solid qualifying campaign for the Churchill Downs showpiece.