Leonard was born in Wolverhampton in 1889, the son of James and Elizabeth Highfield. They were living at 20 Bridge Street in 1901, together with Leonard’s sisters Elizabeth and Caroline. By 1911, he was a cycle finisher at a cycle works, boarding in the home of Thomas Edward Hodson at 42 Grimstone Street, Springfield, Wolverhampton.
In December 1915, Leonard became a Private with the Army Service Corps (number 207773). He served at home from 31 August 1916 until he was discharged on 13 March 1917 as being no longer physically fit for War Service. His trade was given as Cycle Frame Builder, and his address as 42 Grimstone Street, Springfield, Wolverhampton. His pension records state that he had poor sight all his life, which was neither the result of, nor aggravated by, his military service. He was awarded the Silver War Badge (number 151602) on 10 March 1917. His name is listed on the Penn Road Memorial.
He married Elsie Prior in Wolverhampton in 1918, and the couple appear to have had nine children – Leonard (1919), Elsie M. (1921), James W. (1923), Albert (1924), Edith (1926), Phyllis (1928), Hilda E. (1929), Sarah (1932) and Iris (1937). Leonard died in Wolverhampton in 1962.