Family Background and Aristocratic Lineage
Mackintosh was born in London, Canada West, on May 13, 1843, into the family of Leonora Raffles Dickenson and Captain William Mackintosh (b. ca.1809) of Wicklow, Ireland, an officer posted to Canada with the British Army's Ordnance Department, who later served as County Engineer for Middlesex County, Ontario.
His maternal grandfather was Colonel Dickenson, a planter from the West Indies. His mother was the niece of Sir Thomas Stamford Bingley Raffles, founder of the port of Singapore and Lieutenant Governor of Java (1811-1815) and of British Bencooleen (1811-1823) in Sumatra.
His paternal grandfather was Captain Duncan Mackintosh, a Scotsman who had been sent to Ireland with the British Army's Highland regiment during the Irish Rebellion of 1798. The Mackintosh family was of ‘ancient Scottish lineage.’
After the Rebellion, he bought an estate in County Wicklow, and in 1802, married, at Dublin, Alicia Weldon, who is variously described as being the daughter of Lady Weldon, and a niece of the Earl of Dysart, though which ones are meant is not specified. C.H. Mackintosh's mother was Leonora Sophia (d. 1891), daughter of Col. Dickinson, of Jamaica, British West Indies. Through the maternal line, Mackintosh claimed to be close kin to Sir Stamford Raffles, founder of Singapore, one of whose sisters was called Leonora, and one of whose half-aunts, Elizabeth Raffles, married William Carter, Esq., of Jamaica. Paternally, he claimed to be a near relation of the essayist and politician, the Right Honourable Sir James Mackintosh, who was member of the Kellachie branch of the Inverness-shire-based Clan Mackintosh, part of the Scottish Highlands Chattan Confederation.
In addition to C.H. Mackintosh's ties to the ruling class, there is occasional confusion with another Mackintosh author, Charles Henry Mackintosh (1820–1896), a prolific Plymouth Brethren author and evangelist, who was known principally by the initials, C. H. M., which happen to coincide with those of the present subject. Details in this second man's biography indicate that the elder and younger C. H. Mackintoshes were possibly uncle and nephew, or, at least, related (see References).
In nineteenth century colonial Canada, these exalted family connections in Britain and the Empire may have played a role in fostering Mackintosh's ambitions, and aiding him in his later advancement. Coupled with his innate talents, they may also have served to mark him in Conservative Party political circles where, in 1893, Canada's Prime Minister Sir John Thompson clearly viewed him as the more suitable vice-regal candidate over rival fellow Tory, Nicholas Flood Davin, whose own chagrin at Mackintosh's appointment is well documented.
