When Henderson painted this large watercolour, Kingston was the capital of the newly united Province of Canada and enjoyed one of the largest urban populations in Canada West. The Insolvent Subalterns certainly conveys a bustling and burgeoning town, soon to be incorporated into a city. During their leisure hours, British garrison officers often used drawing skills acquired at military college to record sights and activities considered unique to the North American colony, such as sleighing.

The “coachman” driving the sleigh is Lieutenant Dionysius Airey of the Royal Artillery; and the “guard” sounding the coach horn is the artist, Lieutenant Henderson of the Royal Engineers. The third officer is likely Lieutenant Arthur Henry Freeling, also of the Royal Engineers, whose diary now in Library and Archives Canada reveals the exploits and comradery of the these three men. The prominently displayed cottage on the right corner of King and William Streets (no longer there today) was owned at the time by Dr. James Sampson, a leading physician and thrice mayor of Kingston. He also had five daughters. “Paying calls” was a social ritual involving eligible bachelors (preferably military officers) visiting the families of young ladies.

With affection and humour, Henderson documents a garrison friendship–which, by its very nature, was often fleeting. In June of the same year, Airey left Kingston for Quebec and, in July, Freeling left for Montreal. By 1845, after having been stationed in Kingston since 1839, the artist himself would also leave the city and not return again.