[5] In 1951, he began a sentence for various theft offences, serving two years originally at the Mount Penang Training School near Gosford and later at Tamworth Boys' Home.

[6] After time in Fremantle Prison in 1968, he travelled to the United States on a false passport and met Chicago-based crime figure Joseph Dan Testa.

He was later alleged to be part of a plot to bribe State politicians who were planning to set up a casino regulatory board in a bid to curb illegal gambling.

[8][9] In April 1979, an Independent MP for NSW electorate of South Coast, Mr John Hatton, referred to Freeman in Parliament as "the Australian contact man for one Danny Stein, nominated as an associate of notorious American organised crime figures, including Meyer Lansky...".

[10] Despite accusations of murder, assault, race-fixing, bribery, illegal gambling and involvement in the drug trade, Freeman's only criminal convictions after 1967 were for SP bookmaking in 1983 and 1986, resulting in fines of $500 and $5,000.

[14] The series portrayed Freeman as a playboy crime lord and implied that he was indirectly involved in the Mr Asia drug syndicate, and responsible for the unsolved murder of a hitman, Christopher Flannery.