Orlando by Touchstone out of Vulture was owned by Colonel Peel, younger brother to the statesman, Sir Robert Peel. On 22 May 1844 he competed in what is considered to be the 'Dirtiest Derby in history'. The initial winner was a four-year-old called Maccabaeus who was racing under the name of Running Rein a real three-year-old. Orlando finished second and Ionian was third. To make matters worse Leander , a six-year-old to whom an objection was made before the start due to his suspect age, was brought down by Running Rein a furlong into the race. He broke a leg and had to be destroyed. In addition Ratan, the second favourite, and The Ugly Buck were deliberately held back by their jockeys thwarting any chance they had of winning. After the race Colonel Peel brought an action against the winner. During the trial it was revealed that Running Rein and Maccabaeus had been switched two years previously by Abraham Goodman Levy, an untrustworthy gambler. The innocent owner of Running Rein, Mr. A. Wood, had been unaware of this malpractice. In the end the winner was disqualified and Orlando was awarded the race. From this calamity much stricter rules were applied.