July 25, 1941: Born to Maori mother Kataraina Rutene and Pakeha father James Shepherd in Auckland. Raised in Picton and the then impoverished Auckland suburb of Freeman's Bay.

February 1958: Beat up a man "for no reason" and robbed him while out drinking with friends.

March 1958: Sentenced to three years in the rough Invercargill Borstal, aged 16. His deeply ashamed father died a few months later.

Early 1960s: His crimes escalated from burglaries and car thefts to armed robberies. Reached the "pinnacle of NZ crime" by becoming an expert safe-cracker.

1963: While in jail at Auckland's Mt Eden Prison he helped with a number of high- profile escape attempts.

July 1965: An attempted escape turned into the two-day Mt Eden riots in which the prison was severly damaged by fire. As a result, the first maximum-security prison at Paremoremo was commissioned.

1965-68: Considered one of the ringleaders behind the riot, he was kept in solitary confinement at Waikeria Prison, near Te Awamutu, and in Mt Eden's escape-proof "security block" - where inmates saw daylight for only an hour each day. In there with him were the country's most dangerous prisoners, including Bassett Rd machine gun murderers John Gillies and Ron Jorgenson.

1969: One of the "first customers" at the newly built D block in Paremoremo - where he learned the art of setting up dummy companies and shifting money.

1971: Freed from prison, he became a rugby league player in Auckland - where he picked up the nickname Diamond Jim. Though it was a remark on his knack for picking up gorgeous women, he eventually started wearing a 2.5-carat diamond ring.

1975: Met Mr Asia drug syndicate boss Terry Clark at a party in Auckland but declined to work for him. Over the next few years he was a successful bookie in a pub in the Lower Hutt suburb of Taita and had a stake in nightclubs in Auckland.

1977: Joined the Mr Asia syndicate as their banker, laundering their millions and hiding it overseas. Over the next two years he also became Clark's biggest wholesale buyer of heroin, selling it on and pulling in up to A$100,000 a week.

1979: With the heat on after the discovery of the bodies of Kiwi drug couriers Doug and Isabel Wilson near Melbourne, Shepherd began cutting ties to the syndicate.

November 1979: Fled to the United States after Clark was arrested for the murder of Martin Johnstone.

1984: Arrested in San Francisco and extradited to Australia to face drug charges.

June 1986: Jailed for 25 years after being found guilty of conspiracy to import heroin into Australia.

1990: Involved in the riots at New South Wales' Parklea maximum-security prison.

December 1998: Freed from prison after serving 15 years and currently leads a quiet life in Sydney.