In the 1970s, Shepherd established the retail food businesses Partridges[4] of Sloane Street and Shepherd Foods in London, operating both enterprises with his family.[3] He was then an underwriter at Lloyd's of London from 1974 to 1994.[2]
Shepherd was elected Member of Parliament for Aldridge-Brownhills in 1979. The Spectator variously cited him as 'Backbencher of the Year' in 1987, 'Troublemaker of the Year' in 1989, and 'Parliamentarian of the Year' in 1995.[2] He was rated as one of the ten most effective sitting MPs in 1989.[2] In 2010, ConservativeHome listed him as one of the most rebellious Tory MPs.[5]
One of the most significant events in Shepherd's parliamentary career came in 1988 when he introduced his Protection of Official Information Bill,[6] which was to replace parts of the Official Secrets Act 1911, with intent to provide limited protection to some whistleblowers. The government introduced a three line whip which called on its MPs to vote against the bill, even though it was introduced by a member of their own party.[2] This brought considerable debate at the time both in parliament and in the media. The bill was defeated. However Shepherd successfully introduced similar provisions into law in 1998.[3]
Shepherd was a strong advocate of Parliament's power to hold the government to account.[7] Shepherd stood to be Speaker of the House of Commonsin 2000, and won 136 votes: the third-closest to defeating Michael Martin of eleven opponents. When Martin was forced to resign, in 2009, he stood for the position again. An outsider, at 14/1,[7] he won only 15 votes, and was eliminated on the first ballot.[8]