Synopsis In 1987, Merilyn Simonds happened upon a cache of letters, albums, and clippings in the attic of her house in Kingston, Ontario. Among the overflowing boxes and stuffed sugar sacks was a collection of letters from the months immediately after the First World War. It was a one-way correspondence, often scratched in pencil on what looked like toilet paper — 79 letters, some of them 25 pages long, written by a prisoner in Kingston Penitentiary to a young girl who lived on the outskirts of Portsmouth village, on the brink of a prison quarry where convicted men broke stone ten hours a day, doing hard time.

Joseph Cleroux was a thief and a con artist, incarcerated in the country’s most notorious prison, a young man determined that jail would not break or tame him. Phyllis Halliday was a seventeen-year-old school girl who fell under the spell of someone she could never meet or touch, except through their clandestine correspondence. He called himself Daddy-long-legs, she called herself Peggy. Their letters allowed them both to escape the confines of their lives, although the risk entailed in that taste of freedom increased as Joe asked more and more of Phyllis and conditions inside the prison deteriorated. William St. Pierre Hughes was superintendent of the nation’s penitentiaries at the time, a reformer out of favour with his political masters. His fate, like Joe’s and Phyllis’s, was bound to the conspiracies inside Kingston Penitentiary, conspiracies that eventually erupted into the first riot in Canadian penal history.


Joe Cleroux’s letters are reproduced in full, laced together with the story of Pegggy and Daddy-long-legs, set against the stark backdrop of Kingston penitentiary and the village of Portsmouth, a community so in thrall to the prison that it seeped into everyday life. More than a haunting passage through the world of convicted man, The Convict Lover is a compelling journey into the hearts of real people, each caught in a prison, only one of whom escapes.