The only professional in Indian horse racing history to win over 1,000 races both as jockey and as trainer

By Harsh Thakor* 
Pesi Shroff is perhaps the most visible face of Indian horse racing. He seamlessly carried forward the legacy of his cousin Karl Umrigar, who tragically lost his life in an accident. In many ways, Pesi became a symbolic reincarnation of Karl’s aspirations, taking Indian racing to greater heights and establishing records that remain unbroken to this day.
I fondly recall sharing a pony named ‘Proxy’ with him during our childhood in the mid-1970s and watching him ride in his early days at the Amateur Riders Club, long before he turned professional. Born into an upper-middle-class Parsi family, Pesi began his career as a jockey at the young age of 16 and received his license from the RWITC in 1981. He married his childhood sweetheart Tina, Karl Umrigar’s sister, and they have two children, Yohan and Anya. Despite his tall frame, he managed to maintain his riding weight between 51–55 kgs, a testament to his discipline and determination.
While it was his mother, Tehmina Shroff, who introduced him to the saddle, it was his father who instilled in him the habit of introspection and internal growth, pushing him to explore his potential. Support also came from his uncle Jimmy Umrigar and his wife Tina.
In his journey to the top, Pesi overcame countless challenges. What distinguished him was not just talent but an unbreakable discipline and a deeply analytical mind. He may not have been the most stylish or powerful jockey, but none could match his strategic insight, race analysis, and instinctive feel for horses. He had an unparalleled ability to place horses in a race and foresee how events would unfold, executing plans with extraordinary precision.
Pesi’s temperament on the track was unshakable. He had the mental strength to shine in the biggest races and was known for his soft-spoken, gentlemanly demeanour. While he may not have possessed the natural flair of a Vasant Shinde, he more than compensated with meticulous preparation, sound judgement, and a calm confidence in his decisions. He believed in change as a necessary path to growth and innovation. Punters trusted him like few others, and he was often hailed as the quintessential "gentleman jockey."
He won his first race on a horse named “My Squaw.” By the time he became a trainer in 2004, he had recorded 1,750 career wins, including over 100 classic victories and 29 Derby wins—eight Indian Derbies and 21 from other centres. He also won seven Invitation Cups and two Sprinters Cups. Pesi etched his name among the world's best with a hat-trick of Indian Derby wins: on Exhilaration in 1989, Desert Warrior in 1990, and Starfire Girl in 1991, triumphing over elite international jockeys like Lester Piggott, M.J. Kinane, and Walter Swinburn.
Early in his career, support from owners like Goculdas, Shyam Ruia, and Radha Sigtia, and trainers such as Bal Lagad and Uttam Singh, helped him rise. Later, he enjoyed strong partnerships with Bezan Chenoy and Rashid Byramji. He was also retained by liquor baron Vijay Mallya for several years, riding for notable owners like M.A.M. Ramaswamy, D. Khaitan, the Poonawallas, and K. Dhunjibhoy. His record in Indian Derbies and Invitation Cups remains unmatched. Other notable Derby wins came on Enterprising (1984), Revelation (1985), Littleover (1994), Storm Again (2001), and Psychic Flame (2004). His Invitation Cup victories include wins on Revelation (1985), Amorous Knight (1986), Exhilaration (1989), Desert Warrior (1990), Bugs Bunny (1992), Adler (1993), and Storm Again (2001). His Sprinter Cup victories came on Ricardo and Albertini.
He clinched the Pune Derby on Amorous Knight in 1985 for trainer S.S. Shah and on Capricorn in 1986 for Bezan Chenoy. In Bangalore, he won the Derby for J.S. Dhariwal on Classical Act in 1992 and for S. Singh on Fantabulous King in 2004.
Among his finest rides was on Psychic Flame in the 2004 Indian Derby, narrowly beating Estonia. His win on Storm Again in the 2001 Indian Derby, with impeccably timed acceleration in the home stretch, and on Littleover in 1994, showcased his mastery. Yet, like any great athlete, he had moments of misjudgement, such as his rides on Saddle Up in the 1999 Invitation Cup and on Enterprising in the 1984 Invitation Cup.
On Classical Act, he demonstrated artistry by overcoming the colt’s inexperience to win the Derby straight off a maiden race, reminiscent of Lamtarra’s Epsom Derby feat. He also delivered a memorable performance on Sky Rider in the 2002 Pune Derby. His ride on Snow in the 1983 Indian 1000 Guineas was a masterclass in pace judgement.
His win in the 1990 Hyderabad Derby on Sikander-E-Azam, a modestly bred horse, was especially touching—it marked the first and only Derby win for both the owner and trainer. Among the best horses he rode were Continual, Adler, and Exhilaration. Continual, tragically injured before reaching full potential, was on track to become one of India’s best. Pesi’s rides on Exhilaration across three classics looked like poetry in motion.
Controversy struck in 1996 when he was suspended for 13 months by the Madras Race Club for reckless riding on Sea Gazer—a decision that led to protest resignations and court proceedings. Earlier, in 1992, he clashed with RWITC stewards in the infamous "Knight N Day" incident. He also faced suspensions in 2011 and 2013 over positive drug tests. Yet, he always returned stronger, never allowing setbacks to derail his focus.
When Pesi transitioned to training in 2004, he remarked, “I love the sport so much, I want to be associated with it in one way or the other.” Though he considered an administrative role, he chose instead to remain on the turf. It took five years to win his first Indian Derby as a trainer, with the extraordinary filly Jacqueline in 2010—India’s first filly to win four classics (1000 and 2000 Guineas, Oaks, and Derby) in a single season.

Pesi is the only professional in Indian racing history to win over 1,000 races both as a jockey and as a trainer. His 1,000th win as a trainer came in 2018 with Khartoum, ridden by N.S. Parmar. He has won the Indian 1000 Guineas multiple times as both jockey and trainer, including on Mariinsky, Myrtlewood, and Mrs Patmore. His Indian Oaks wins include Blue Ribbon (2007), Roberta (2019), and Smashing (2012), when he saddled the top three finishers in the same race—an unprecedented feat.
He won the 2017 Invitation Cup with Temerity, trained under his guidance, in a record time of 2:28.85, defeating favourite Hall of Famer. In 2013, Jeremiah gave him back-to-back Derby wins—first in the Deccan Derby and then the Pune Derby within two weeks. Other key triumphs include Phenomenale in the 2008 Pune Derby, Tiger Top’s wins in Kolkata and Mumbai, and Sacred Roman’s Stayers’ Cup win in 2019.
In the Sprinter’s Cup, Adam’s victory at age six in 2016 underlined Pesi’s ability to keep horses at peak performance. Adam also won the prestigious Kakatiya Million. His other Sprinter’s Cup champions include Attila (twice) and Solomon.
Pesi Shroff’s journey as both jockey and trainer is a saga of endurance, excellence, and unrelenting dedication. He remains one of the greatest icons of Indian racing, not just for his victories but for the manner in which he achieved them—with dignity, intelligence, and grace.
---
*Freelance journalist