Wayward Lad, whose was trained by Tony, Michael and Monica Dickinson at various stages is, ironically, probably best remembered for not winning the Cheltenham Gold Cup on two occasions. On the first, in 1983, when he finished third behind stable companions Bregawn and Captain John in the year when Michael Dickinson saddled the first five finishers. On the second, in 1986, he led halfway up the run-in, only to be overhauled in the closing stages by Dawn Run, in the year she completed the Champion Hurdle – Cheltenham Gold Cup double.
Nevertheless, Wayward Lad was a hugely talented steeplechaser. All in all, he won 28 of his 55 races, including the King George VI Chase at Kempton (three times), the Betfred Bowl at Aintree (twice), the Charlie Hall Chase at Wetherby and the Edward Hanmer Memorial Chase at Haydock. John Francome recalled his victory in the King George VI Chase in 1982 with more than a hint of Schadenfreude, saying, “I remember the year I won on Wayward Lad taking great pleasure in the success because the runner-up, Fifty Dollars More, was a horse I’d been jocked off from Fred Winter’s yard, because he was owned by Sheikh Ali Abu Khamsin who retained Richard Linley.”
At the end of his racing career, Wayward Lad spent his retirement with former trainer Michael Dickinson in Fair Hill, Maryland and died in 2003 at the age of 28.