July 8, 1895 - Norman J. Ryan
What distinguished Ryan from other career criminals of his era was the degree to which he manipulated not just victims but institutions — parlaying a carefully constructed prison persona into a cause célèbre for Canadian penal reform, only to resume his criminal life upon release. His story became a cautionary episode in the history of rehabilitation advocacy, illustrating how public sympathy, once mobilized, can be systematically exploited.
From Wikipedia
Norman "Red" Ryan, (8 July 1895 – 23 May 1936) was a notorious gangster in early 20th century Toronto, Ontario. He came from an Irish Catholic upbringing and he took to the streets as a young man to engage in crime. He was called the 'Jesse James of Canada' and he was known for armed robbery, safecracking, and other major theft. He killed six people in his career. He was arrested in Minnesota on 14 December 1923 and given life imprisonment, which he served in Canada. He served his sentence at Kingston Penitentiary. He was killed in a liquor store in Sarnia by a police officer after being shot 3 times.
In prison he lived the life of a model prisoner and became a poster child for the prison reform movement in Canada.
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