Lester Piggott: The jailbird soars again In 1987, having retired from racing two years earlier and switched to training at his Eve Lodge Stables, Lester Piggot was jailed for three years for tax irregularities and eventually served 366 days before being released on parole. In 1990, having been stripped of his OBE on his release from jail, he stunned the racing world by returning to competitive racing at the age of 55, and crowned an extraordinary comeback by winning the Breeders? Cup Mile on Royal Academy. As if to prove it was no fluke, he won his final Classic two years later when he took the 2,000 Guineas on Rodrigo de Triano. Piggott finally retired for good two years later, having ridden nine Derby winners and been champion jockey on 11 occasions.