Shaw was admitted as a solicitor of the New South Wales Supreme Court in 1975 and as a barrister of that same court the following year. On 12 November 1986, Shaw was appointed Queen's Counsel. He specialised in industrial law.
Politics
Shaw was a member of the Labor Party. During the 1970s Shaw was a leading intellectual figure of the NSW ALP left. He frequently contributed to the left's publication Socialist Industrial Labour and later Challenge. With others such as Joan Evatt, Wayne Haylen, Peter Crawford, Laurie Ferguson, and Pam Allan he successfully organised the unprecedented left takeover in NSW Young Labor in 1973–74, becoming Senior Vice President. During this period he was an official of the Public Service Association of NSW and later a solicitor with labor law firm Taylor & Scott. Shaw was a candidate for the New South Wales Legislative Assembly seat of Eastwood in the 1981 NSW election. He was defeated by the incumbent, veteran Liberal Jim Clough. Shaw was appointed to fill a casual vacancy in the New South Wales Legislative Council in May 1990, representing the Labor Party. The ALP was in opposition at the time, and Shaw served as Shadow Minister for Industrial Relations and Local Government from 1991 to 1995.
Minister
Upon the election of the ALP to government in March 1995, Shaw became Attorney General and Minister for Industrial Relations, positions he held until 2000. Shaw was also the Minister for Fair Trading from 1998 to 1999. As Attorney-General he led a push in 1996 to censor online information.
Retirement
In 1998 Shaw failed to gain a winnable position on the ticket in left wing preselection for the Upper House. His career was eventually "saved" by the right wing Head Office group who moved him to top of the combined ticket. Clearly disillusioned with factions, Shaw observed at the launch of the Henry Parkes Foundation on 4 June 1999 that "he helped pioneer the faction system that dogs state politics yet – and last year threatened the career of a brilliant Attorney General". Despite his conflicts with factional figures, however, Shaw was regarded as an "iconic figure" within the ALP. Shaw retired from the Legislative Council in 2000.
Judicial career
Shaw was sworn in as a Judge of the Supreme Court of New South Wales on 4 February 2003. On 13 October 2004, Shaw crashed his car into a parked vehicle near his Sydney home. He was taken to hospital, where a blood sample was taken for testing; however, the sample disappeared. Under pressure from the Opposition Liberal Party, the Police Integrity Commission initiated an inquiry into the circumstances of the sample's disappearance. In November 2004, Shaw voluntarily surrendered a second blood sample to the police, resigning from the Supreme Court on 12 November 2004. He was later charged with negligent driving and driving while drunk. Shaw lost his driving licence for a year and was fined A$3,000. Shaw served as a Supreme Court justice for 647 days.
