Later Life
After spending a few months working for his father-in-law as a trainee mechanic, Ryan decided that more money could be made cutting timber near Marysville and Licola. When it was too wet to cut timber, Ryan got a job painting for the State Electricity Commission. By 1952 the Ryan family was living in Noojee.
Trouble with the law started when his rented house burnt down. Ryan was away for the weekend in Melbourne when the arsonist struck. The arsonist was caught and claimed that Ryan had put him up for it, he also claimed that Ryan wanted the house burnt to claim insurance money. His first appearance in court was in Warragul, Victoria in 1953 when he was acquitted on a charge of arson.
In 1956 Ryan appeared in court for passing bad cheques in Dandenong. He was given a bond. His next appearance in court was after he issued a large number of forged cheques in Warrnambool. His partner was caught with the goods purchased with the bad cheques and handed Ryan over to the police. He received another a good-behaviour bond. The arresting detective gave a favourable character reference on Ryan's behalf.
After being apprehended for robbery in April 1960, Ryan and his accomplices escaped from the Melbourne City Watch House but were recaptured several days later. On 17 June 1960, Ryan pleaded guilty in the Melbourne Court of General Sessions to eight charges of breaking and stealing and one of escaping from legal custody. He was sentenced to eight and a half years imprisonment.
Ryan first served prison time at Bendigo Prison. Here, under Ian Grindlay (who would later become the Governor of Pentridge Prison), he appeared to want to rehabilitate himself. He was a model prisoner, his time in prison was productive and he exhibited a disciplined approach to study, completing his Leaving Certificate (the equivalent of 11 years of formal schooling). He was studying for his Matriculation (the successful completion of 12 years of formal schooling) when he was released on parole in August 1963. He was regarded by the authorities as a model prisoner.
After working as a clerk for a couple of months, Ryan went to lunch and never returned. He had started robbing butcher shops and used explosives to blow their safes.
Ryan and two accomplices were caught after another butcher shop robbery on 4 January 1964. He was charged with breaking and entering and theft offences on 6 January 1964. Bailed on 3 February 1964, Ryan skipped town and fled to New South Wales. He later admitted to nine robberies in New South Wales between 4 April and 11 July 1964. On a visit home on 14 July he was caught by Victorian Police in the early hours the next morning. On 13 November 1964 he received an eight-year prison sentence for breaking and entering. He was sent to Pentridge Prison.
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