The Convict Lover: A True Story

Steve Pitt is a Toronto-based freelance writer and an award-winning journalist. He has written many young adult and children's books, including Day of the Flying Fox: The True Story of World War II Pilot Charley Fox.

In the early part of this century, convicted felon Joseph “Daddy Long
Legs” Cleroux served two years less a day at hard labor in the
Kingston Penitentiary. Phyllis Halliday, a lonely 17-year-old
high-school student, lived beside the prison’s quarry when Cleroux was
a prisoner. Twice a day, Joe’s chain gang passed Phyllis’s home on
its way between prison and quarry. After Cleroux saw Phyllis in her
backyard, he began the dangerous game of dropping illicit notes for her
to find. Note by note, Phyllis was drawn into Joe’s convict world.
Trapped in her own personal cell of small-town drudgery, Phyllis dared
to hope that someday she and Joe might start a new life together.

In 1987, writer Merilyn Simonds, while exploring the attic of her old
bungalow in Kingston, Ontario, discovered a trove of these letters from
Cleroux to Halliday. This one-sided correspondence, which gives us
Cleroux’s personal insights into early 20th-century Canadian prison
life, is the foundation of the book, which Simonds augments with
excerpts from historical records, government documents, and period
photographs. She also draws parallels between Phyllis Halliday’s
personal struggles and those of William St. Pierre Hughes, the federal
superintendent of penitentiaries whose unpopular attempts at prison
reform also earned him a reputation as a convict lover. With its
thorough research and fine writing, this is an exceptional book.