Derek William Nightingale was born on 19 September 1942. He became head lad to owner-trainer Alex Greenshields, whose yard was at East Herrington, near Sunderland. Greenshields had previously trained winners on the Flat but had relinquished his licence in 1956 and now just held a permit to train his own horses.
Derek Nightingale first took out a jump jockey’s licence in 1962/63 but had to wait until the end of that season to ride his first winner.
In fact, he rode his first two winners within 48 hours, both coming on the Greenshields-trained Ring a Bell at Hexham in June 1963.
Ring a Bell was to provide Derek with all four of his winners between June 1963 and October 1965.
He eventually parted from Greenshields’ yard and joined the much higher profile trainer Verly Bewicke, for whom he rode Albany Herald to victory at Huntingdon on August Bank Holiday 1967.
After just one season with Bewicke he moved to the smaller yard of J Palmer, who trained at Grimston, near Melton Mowbray.
Derek rode what was to be the last of his seven winners on Palmer’s Over Sleep at Doncaster on 3 March 1969.
He left Palmer at the end of that season and journeyed back north, spending one year as head lad to Lord Kilmany, who trained horses under permit at Cupar, in Fife, but stayed only one year there before joining the then emerging yard of Tony and Monica Dickinson at Gisburn at the start of the 1970/71 season. He held a jockey’s licence for the next three seasons but rides were few and far between and he failed to ride any more winners.
Derek was tall for a jockey at 5ft 10in and was known as ‘Bones’ by his fellow jockeys due his skeletal frame which allowed him to ride at 9st 7lb. In his autobiography ‘Good Horses Make Good Jockeys’, Richard Pitman remembers that Nightingale “believed that trainers would not give rides to lads with big feet because time had taught them that boys would grow to match their feet, becoming too heavy to make jockeys. The answer for ‘Bones’ was to cram his size 9½ feet into size 7 jodhpur boots every morning.
This ruse worked and he duly got his rides, but being so devoid of natural cushioning he broke something nearly every time he fell, and eventually without any notice disappeared from the riding scene.”
Derek listed the best horses he rode as Ring a Bell and Verona Forest. He listed his interests as car and motor cycle racing.
He rode a total of seven winners, these being in chronological order:
1. Ring a Bell, Hexham, 1 June 1963
2. Ring a Bell, Hexham, 3 June 1963
3. Ring a Bell, Catterick, 30 November 1963
4. Ring a Bell, Catterick, 30 October 1965
5. Albany Herald, Huntingdon, 28 August 1967
6. Paddy Field, Wincanton, 29 February 1968
7. Over Sleep, Doncaster, 3 March 1969.