[1] From 1888 to 1908, Staples worked for the Telegram as a staff artist, reporter, and political cartoonist,[3] and illustrator for the J. Ross Robertson Collection.

Thereafter, Staples became a well-known artist, illustrating a number of books, executing commissioned murals, and producing a vast oeuvre of paintings, watercolours and etchings.

Thomson, who was artistic but inexperienced, may have been intrigued by Staples, a master watercolourist, who made every effort to 'catch the light' with his quickly rendered pictures.

Many good times were spent at[10] 69 Hogarth Avenue, in Toronto's east end, a favorite meeting place for artists, musicians, writers, etc.

Visitors included opera star Bertha May Crawford, architect Eden Smith, banker and art patron Sir Byron Edmund Walker who purchased many of Staples' works, the celebrated cellist Leo Smith and a host of other artists, poets, writers, educators, ministers, musicians, politicians and bankers.

Perhaps the most enigmatic visitor was William Leonard Hunt, also known as The Great Farini, who pitched a tent in the backyard and stayed for the summer.

In later years, Staples' son Will and his close friend Charles Comfort attracted a younger generation of Toronto's arts community.