Born and bred in Co. Limerick, ‘Big Ron’ Barry joined Wilfred Crawford at Haddington, East Lothian as a conditional jockey in 1964 and rode his first winner in Britain, Final Approach, in a novice hurdle at Ayr in October that year. Barry enjoyed plenty of early success, winning the Great Yorkshire Chase and the Scottish Grand National on Playlord and the Massey Ferguson Gold Cup on Titus Oates, both trained by Gordon W. Richards, in 1969 and the Whitbread Gold Cup on Titus Oates in 1971.
Indeed, it was as stable jockey to Richards at Castle House Stables in Greystoke, Cumbria that Barry made his name. In 1972/73, Barry won the Cheltenham Gold Cup on The Dikler, trained by Fulke Walwyn, beating the luckless Pendil, trained by Fred Winter and ridden by Richard Pitman, by a short head. Elsewhere, he also won the John Whitbread Gold Cup, for a second time, on Charlie Potheen, also trained by Walwyn, and at the end of the season had ridden a then record 125 winners to become Champion Jockey for the first time.
The following season, 1973/74, Barry rode 94 winners, including The Dikler in the Whitbread Gold Cup – a third win in four years for the jockey – but, nevertheless, retained the jockeys’ title. He also rode in the 1973 Grand National, in which Crisp failed, by three-quarters of a length, to concede 23lb to Red Rum in probably the most dramatic finishes ever seen at Aintree. Unfortunately, his mount was miles behind the principals when refusing at the fourth last fence. Barry retired in 1983, at the age of 40, having ridden 823 winners under National Hunt Rules.