He was, with fellow Angaston student James Scandrett and Oscar Nootnagel from Adelaide Educational Institution, admitted as a cadet to the Civil Service in July 1879,[4] and worked in the office of the Colonial Architect.
[6] In 1880, as "J. J. H. Leonard", he won a prize for an India ink drawing,[7] and after finding a ready market for his pen-and-ink sketches, caricatures and lithographs (as "Leo") in the Port Adelaide News, The Lantern, Adelaide Punch and Frearson's Weekly, he felt sufficiently confident to quit his job and became chief cartoonist for The Lantern, which at that time boasted a fine stable of artists: A. S. Broad, J. H. Chinner, Alfred Clint, H. J. Woodhouse, James Ashton and John Hood.
[8] Leonard had other talents: he was a capable light tenor, and an actor, one of the more successful players in H. J. Woodhouse's short-lived Yorick Club of amateur thespians, providing additional entertainment with "lightning sketches" of local celebrities when they played at large towns such as Kapunda[9] and Gawler.
[11] In 1888 he famously exhibited, in a Bourke Street shop window, an oil painting satirizing the free market champion Henry Parkes as King Lear with the dying Cordelia (representing the NSW economy) in his arms.
[13] In 1893 he and Gilbert Probyn Smith (died 1905),[15] as proprietors of a Sydney publication named Police News, were tried for criminal libel,[16] but the Attorney-General declined to prosecute.
These illustrations were carried through to the single volume condensed version, As a challenge, or proof of his skill with the pen, in 1901 he drew a 21 by 18 inches (530 mm × 460 mm) portrait, on card, of the Duke and Duchess of Cornwall and York, surrounded by Australian wildflowers and the representation of an ornamental frame, all consisting of one line only, without a break or crossing,[21] and of varying width to create light and shade,[22] commencing at the tip of one nose and terminating at the other.