Within 10 years he lost his brother, two grandchildren, his two sons, and his wife, and finally he died, on October 29, 1862, in virtual obscurity and penniless, at the home of his son-in-law.
John Counter was an avid businessman, and invested heavily in Kingston’s commercial district, was involved in the real estate and transportation industries, and owned both a foundry and a sawmill.
He also proposed building the Wolfe Island Canal (now abandoned) to provide quick water transportation to and from Cape Vincent.
Counter promoted the incorporation of Kingston as a town judging that it would bring increased business and improve property values.
He resigned from the office of mayor in June 1855 because his shares in the local gas company were considered to constitute a conflict of interest; and only a few months later, in October 1855, he could not meet a large mortgage payment and his financial obligations forced him into bankruptcy.
Town Council members asked Mayor Counter to sit for his portrait, which was delivered in September 1842 at a cost of £17.10 and was paid for by the councilors personally, not from civic funds.
It has been loaned to the Art Gallery of Ontario, where they made the existing slides of the painting that have been copied for archival institutions nationwide, and was stored at the City of Kingston facility at 19 Queen Street until it received restoration work in the late 1970s.