Renowned bookmaker ‘Fearless Freddie’ Williams endured a devastating week at the Cheltenham Festival in 2006, losing £925,000 to prominent horse owner JP McManus in a single day’s betting.
McManus’ Record-Breaking Betting Day
JP McManus, whose net worth stands at approximately £1.8 billion, celebrated one of his most lucrative betting successes that year. The Irish magnate, who marked his 75th birthday on the opening day of the recent festival, secured nearly £1 million in winnings from stakes placed solely with Williams. McManus boasts over 80 Cheltenham victories and aims to add more to his impressive tally.
Two key bets sealed Williams’ substantial losses. First, McManus wagered £100,000 on his horse Reveillez in the Jewson Novices Handicap Chase at 6/1 odds. Jockey AP McCoy rode to a stunning victory, delivering a £600,000 profit.
McManus nearly hesitated on the bet after McCoy ed concerns in a Telegraph column about the horse’s jumping. “I got a little bit nervous when Tony, writing in the Telegraph, said he was worried about his jumping,” McManus admitted. “But I couldn’t let him run loose at 6-1.”
Boosted by that win, McManus backed outsider Kaldoun with a £5,000 each-way bet in the Pertemps Final Handicap at around 50/1 odds. The long shot triumphed, yielding another £325,000 return.
Robbery Compounds the Losses
Williams’ misfortunes extended beyond the track. That same evening, a balaclava-clad gang robbed him and his daughter of about £70,000 as they drove back to their hotel in a Jaguar. Thieves smashed the windows after blocking the vehicle with a Land Rover and Vauxhall Astra, later found burned out nearby. Police confirmed tens of thousands of pounds were stolen.
Combining the betting losses and robbery, Williams’ total hit £1 million that day, excluding any gains from other clients during the major racing event.
Williams’ Legacy in Racing
Scottish millionaire Williams, known for accepting six-figure bets from racing’s elite, passed away from a heart attack in June 2008 at age 65. His bold approach at Cheltenham left a lasting mark, though not always favorably.

