Harry Redknapp’s connection to the Boxing Day race has been a lifelong journey, starting from his days as a footballer and manager to his current status as a beloved public figure since winning “I’m a Celebrity…Get Me Out of Here!” in 2018. An avid horse racing enthusiast since his managerial days in Bournemouth in the 1980s, Redknapp may finally see his dedication pay off with his horse, The Jukebox Man, who boasts a record of seven wins and one loss and is poised to compete in the prestigious Ladbrokes King George VI Chase at Kempton on Boxing Day. This event marks a special occasion not only for Redknapp but also for his family, with his wife Sandra surprisingly joining in the festivities.
At 78, Redknapp enjoys a quieter life, often spotted enjoying tea at his trainer’s bar or watching football at Newbury Racecourse, and hosting popular intimate events sharing his football stories. Faced with choosing between a short trip to watch Bournemouth play and a much longer drive to see The Jukebox Man race, he chose the latter, demonstrating his strong commitment to horse racing—a passion sparked by his grandmother, Maggie, who secretly placed bets during a time when bookmaking was illegal.
Reflecting on his early football career in the 1960s, Redknapp recalls how gambling was deeply ingrained in the sport’s culture, with players like West Ham’s Johnny ‘Budgie’ Byrne combining their training routines with betting rituals. His initial involvement in horse ownership began at Bournemouth, joining a syndicate with several club figures, owning a horse named Slick Cherry.
Over time, Redknapp became involved with numerous trainers and horses, but none have been more successful than his collaboration with Ben Pauling, who trains The Jukebox Man and has delivered four wins including a Cheltenham Festival victory with Shechem Up Alley. Redknapp even named a horse “Shake ‘em Up Alley” after a phrase football fans would shout to encourage him during matches.
Despite some physical challenges and setbacks, including an injury that sidelined The Jukebox Man last season, the horse has shown resilience and promising form recently. While Sandra, his wife, rarely attends races, she hopes to avoid being considered bad luck if their horse doesn’t win. As Redknapp looks forward to the upcoming World Cup with cautious optimism, his true excitement shines for The Jukebox Man’s Boxing Day race—a nail-biting event where every jump keeps him on edge.
Fan Take: This story underscores the deep passion and personal connection many have with horse racing, showing how the sport can bring lifelong joy and excitement beyond just the racing world. For horse racing fans, Redknapp’s journey highlights the sport’s enduring appeal and the thrill of rooting for promising British-trained talent in major national events.

