Richard Cullen constitutes a curiosity in Irish racing annals. He did indeed ride Flying Dinah to victory in the Irish 1000 guineas of 1925. Moreover, he did so while still an apprentice – a rare occurrence indeed.
Richard Cullen appeared for the first time in the 1920 Irish Racing Calendar, as a flat apprentice, joined a year later by Patrick and Thomas Cullen. In those days the Calendar did not disclose the name of the trainer to whom an individual was indentured. Nor did it do so in 1922, when R. Cullen was reported by the starter – Leslie Loxley 'Ginger' Firth – to the Curragh stewards for 'pulling his horse up at the start.' Whatever defence the 6-stone-something youngster advanced, it was successful. 'The Stewards exonerated him from intentionally interfering with his horse'.
Trainer D.B. McKenna clearly took the hint, giving Oola one more run down the field at Baldoyle before returning to the scene of the crime in November, this time with Tommy 'Scotchman' Burns in the saddle. Backed down to 6/4 favourite – 4/1 bar one – Oola skated up by 2½ lengths.
Two years later R. Cullen had already come to the Curragh stewards' attention, asked to explain his mount's running when Maid of Troy had finished a close second. His riding had been 'considered open to grave suspicion and he was cautioned as to his future conduct'. Worse lay in store. At the May 1924 Curragh meeting 'Mr J.J. Parkinson lodged a complaint against R. Cullen for not carrying out his instructions as to the riding of Radio Girl [joint-favourite, 2nd, beaten 4 lengths by the other joint-favourite]. The Stewards withdrew R. Cullen's riding licence, but restored it to him on June 5th'.
Hardly had the stewards had time to grumble over Parkinson's paranoid suspicion of all jockeys when another troublesome trainer intruded. 'Mr J.T. Rogers reported Mr J.J. Parkinson for engaging R. Cullen (Mr Rogers' apprentice) to ride for him without first obtaining permission to do so'. Consternation; teatime postponed, again, staff summoned. Eventually they found the solution. 'There being no Rule directly bearing on such a case the Stewards considered any action on their part unnecessary'. Whew!
R. Cullen's 1925 season had yet to yield a winner when he was told he was riding Flying Dinah in the Irish 1000 Guineas. He had ridden her three times as a two-year-old and again on her seasonal debut. Useless. She could only be running in the Guineas at her owner's insistence. The punters shared his view, rejecting Flying Dinah at any price. No need to look beyond Lady Ludlow's Bright Maid, five-time juvenile winner for Harry Ussher, sent over now from Sam Pickering's Newmarket stable and ridden by fashionable Jack Leach.
The form book records that Flying Dinah carried Richard Cullen through the heavy going to a clearcut victory over Maqueda (Jack Moylan) and Carlovia (Jas Doyle). Bright Maid was not in the first eight. A year and a change of trainer elapsed before Flying Dinah won again for owner-breeder Captain Gerald Fitzgerald Dunne, longtime manager of Punchestown racecourse and owner of the Blackhall Stud, Clane. Flying Dinah died there in 1933, without producing a single flat winner. Curiously, her portrait, with Morny Wing in the saddle, is preserved in 'Racing at Home and Abroad'.
Richard Cullen rode a further seven winners that season, adding just two more in 1926, no longer able to claim the apprentice allowance, automatically forfeit on turning 21, then and for decades to come. Persevering until June 1932, he did not renew his licence. Nor did he simply transfer to England. Presumably he went further afield, eventually meeting his end in India in 1937.