Rupert ‘Ruby’ Walsh, who retired from race riding, with immediate effect, after winning the Puchestown Gold Cup on Kemboy on May 1, 2019, has the distinction of being the most successful jockey in the history of the Cheltenham Festival. Indeed, he was leading jockey at the Festival a record eleven times – in 2004, 2006, 2008-2011 and 2013-2017 – and his career total of 59 winners at the March showpiece meeting is some way ahead of his nearest rival, Barry Geraghty, with 43.
‘Mr. R.Walsh’, as he was listed on the racecard, opened his Cheltenham Festival aboard Alexander Banquet – also, coincidentally, the first of 213 Grade One winners he rode during his career – in the Weatherbys Champion Bumper in 1998. Walsh turned professional later that year and, over the next two decades, won each of the four main ‘championship’ races at least twice apiece.
Arguably his most memorable victories came aboard Kauto Star in the Cheltenham Gold Cup, in 2007 and, especially, in 2009, but he also won the Champion Hurdle four times, the Queen Mother Champion Chase four times and the Stayers’ Hurdle five times. Indeed, he won the Stayers’ Hurdle, known at the time as the ‘World Hurdle’, on the same horse, Big Buck’s, four years running in 2009, 2010, 2011 and 2012. Just for good measure, Walsh also won the Ryanair Chase – introduced to the Festival programme in 2005, as a ‘championship’ steeplechase over the ‘intermediate’ distance of 2 miles 5 fulongs – four times, most recently on Un De Sceaux in 2017. He rode his final Cheltenham Festival winner, Klassical Dream, in the Supreme Novices’ Hurdle in 2019.