Weston was the son of a railway waggon driver. Through his father, who was a fan of multiple championship winning jockey Steve Donoghue, he developed an interest in the sport of horse racing. Aged 14 and weighing just 4 st 3 lb, he became apprentice to Middlehamtrainer Ned McCormack, a stable controlled by a bookmaker.
Career
After demonstrating his ability riding Redhead, winner of the Liverpool Summer Cup, for trainer George Lambton, Lambton recommended Weston to Lord Derby to be his retained jockey. Weston rode for Lord Derby for ten years, winning nine Classics. These started with a win on Tranquil in the 1923 St. Leger, followed by Sansovino in the 1924 Derby at a muddy Epsom. Two years later he was champion jockey in the year that the rider who would come to dominate the championship for the next thirty years, Gordon Richards, was out for nearly the whole season with illness. He would go on to ride the Horse of the Year in five of the next seven seasons – Colorado, Fairway, Gold Cup winner Bosworth and Hyperion, who would go on to become one of the 20th century's foremost sires. It is argued that Weston should have won himself another Derby with Fairway, but his chance was lost after fans mobbed the horse at the start. The horse eventually proved himself of the highest order in winning the Eclipse Stakes, the St. Leger and the Champion Stakes in two successive years. In 1933 Weston on Hyperion recorded what has been called "the greatest Derby-winning performance of all time" beating high class rivals by an official margin of four lengths, which from photographs has been shown to be closer to eight. Doubts were raised as to the manner of the victory, however, with the suggestion that Weston was aided in his victory by Steve Donoghue, on Hyperion's stablemate Thrapston, securing a clear passage for him. Hyperion followed up in the St. Leger. The partnership between Lord Derby and Weston was dissolved in 1934, without any explanation. It has been suggested that Weston was in conflict with Colledge Leader, Lambton's successor as Lord Derby's trainer, a situation exacerbated when Hyperion lost that year's Ascot Gold Cup. Weston's career was not the same afterwards, although, after serving with the Royal Navy during World War II where he saw active service and was sunk twice, he returned to win the 2,000 Guineas on Happy Knight and a Lincolnshire Handicap on Langton Abbot.
During his career, Weston was a very popular jockey and has been described as "a dashing jockey, with very sympathetic hands" and "combining great dash and courage... but liable to be somewhat erratic." Of his riding, author Quintin Gilbey wrote, "No jockey rode a more vigorous finish and his records showed that though inelegant he was most effective. He was in fact a far better jockey than he appeared to be from the stands."
Retirement
He retired in 1950 and stayed in Newmarket. In later life he was a "sad figure", having spent all the money he made. He died, aged 78, in 1981 at Ely Hospital.
