# Renowned Cheltenham-Winning Jockey Tom O'Brien Passes Away at 39 The decorated rider and family man died following a lengthy battle with cancer. - **Source:** [Sky Sports – News](https://www.skysports.com) - **Published:** 2026-11-11 - **Topic:** [sports](https://brifing.si/c/sports) - **Original article:** - **On Brifing:** https://brifing.si/s/7e6f1ee5-bb79-4a2a-b216-31b9d1055eb5 ## Career and Legacy Tom O'Brien, a Wexford-born jockey, has died at 39 following a battle with cancer. Retiring in April 2023, he secured over 1,076 career winners. His professional journey began in Ireland before he moved to the UK, where he spent his entire career working closely with trainer Philip Hobbs until his retirement. ## Major Racing Achievements O'Brien achieved five Grade One successes throughout his career. His Cheltenham Festival victories included the 2009 Fred Winter with Silk Affair and the 2022 Pertemps Network Final with Third Wind. Additionally, he famously rode Dream Alliance to victory in the 2009 Welsh Grand National, an underdog story later adapted into a film. ## Partnership with Thyme Hill A defining chapter of his career was his partnership with the fan-favourite horse Thyme Hill. Together, they secured significant victories, including the 2021 Liverpool Hurdle at Aintree and the 2022 Kauto Star Novices' Chase. Trainer Philip Hobbs noted that these successes highlighted O'Brien's reliability and talent as a top-tier professional rider. ## Professional Evolution O'Brien spent much of his career as the second jockey to Richard Johnson at the Hobbs yard. Following Johnson's retirement, O'Brien stepped into the role of first jockey. His breakthrough season occurred in 2006/07, during which he rode over 100 winners, cementing his reputation as a hardworking and highly consistent racing talent. ## Personal Tributes Colleagues and industry figures have expressed deep sorrow over his passing. British Horseracing Authority CEO Brant Dunshea praised O'Brien’s kindness and loyal friendship, noting he was held in the highest esteem across the sport. Fellow jockeys and trainers remembered him as a humble, smiling gentleman who was a joy to work alongside. ## Family and Support O'Brien is survived by his wife, Hayley, and their two sons, Archie and Toby. Trainer Philip Hobbs, who maintained a close relationship with O'Brien after his retirement, highlighted the tragedy for his young family. The racing community has rallied to provide support, comfort, and remembrance for the devoted husband and father. ## Industry Impact The loss of O'Brien has resonated on both sides of the Irish Sea. His career was defined by dedication to the UK racing circuit, where he secured all but one of his 1,076 victories. His influence extended beyond the track, touching the lives of countless peers, trainers, and fans of the sport. ## Reflecting on Loss The passing of a rider at 39 serves as a somber reminder of the fragility of life. As the racing world processes this news, the focus remains on honoring his professional brilliance and personal character. He leaves behind a legacy of integrity, hard work, and deep connections within the close-knit equestrian community. ## Sources covering this story - [Sky Sports – News — Cheltenham Festival-winning jockey Tom O'Brien dies at 39](https://www.skysports.com/racing/news/12040/13610855/tom-obrien-cheltenham-festival-winning-jockey-dies-aged-39) - [RTÉ Sport — Renowned Jockey Tom O'Brien Passes Away at 39](https://www.rte.ie/sport/racing/2026/1111/1598809-wexford-born-jockey-tom-obrien-dies-aged-39/) --- _Summary written by Brifing from the original reporting. Copyright in the original article belongs to its publisher; read the full piece at the link above._