Prior to becoming an MP Legg was a director of Hillsdown Holdings, one of Britain's biggest food groups at that time and owner of leading brands such as Typhoo tea, Hartley's jam and Buxted chickens, having joined the firm in 1978. He became company secretary in 1982 and a director in 1986. He left Hillsdown "by mutual consent" in September 1992 with a 'golden handshake' of £200,000 "after it was decided to replace him with someone who could devote their full energies to the job."
Career in local government
Legg – an accountant and tax specialist – entered politics in 1978 as a Conservative councillor for the Regent's Park ward on Westminster City Council. He became the Conservative Chief Whip on the council during Dame Shirley Porter's leadership. He was later linked with the 'homes for votes scandal' in which council homes in eight key marginal wards were sold instead of being re-let to council tenants or used to alleviate homelessness. Believing that council tenants were more likely to vote Labour, the Conservative council intended that this strategy would result in "a pattern of tenure which is more likely to translate into Conservative votes." A second independent inquiry identified Legg as the chairman of a secret Westminster council committee meeting that took the decision in 1989 to place 100 homeless families, including 150 children, in two dilapidated tower blocks already known to be full of asbestos. A report from 1983 had warned: "It is considered that these two tower blocks... may provide the greatest potential for asbestos release within residential accommodation in Britain." The official inquiry found that it was "abundantly clear" that the committee knew that the tower blocks, Chantry Point and Hermes Point in Paddington, had asbestos problems and were in a terrible condition. The District Auditor also found that the decision, "leaving aside the serious ethical concerns that it raised, was unlawful because it was taken by a secret and unaccountable group." The scandal was the subject of an exposé by social affairs programme Public Eye, broadcast on 30 November 1995 on BBC Two. Legg's time as a councillor and his conduct in public life and business were the subject of a joint investigation by The Guardian newspaper and the BBC Radio 4Today programme in May 2003.
In 1992 Legg co-authored Maintaining Momentum: a Radical Tax Agenda for the 1990s which proposed a reduction in the basic rate of income tax to 20%, the abolition of Inheritance Tax and temporarily raising the threshold for higher rate income tax to £100,000, followed by its abolition.
Welfare reform
In 1993 Legg was the co-author, with Iain Duncan Smith and 3 other members of the NTBG, of a report which proposed cutting £8 billion from the social security budget. The report made a number of recommendations:
Merging all means-tested and other non-contributory benefits into a single benefit called "whole person benefit"
Privatisation of the National Insurance "pay-as-you-go" benefit system and introduction of private pensions and private insurance against unemployment, long-term sickness and invalidity
On 14 February 2003 Legg was controversially appointed by Iain Duncan Smith to be the new Conservative Party Chief Executive – "against the wishes of the party's ruling board" – and Chief of Staff of Duncan Smith's private office. The appointment was vetoed by the board and Legg, described as Duncan Smith's "right wing ally unpopular with many MPs", resigned on 7 May 2003 with a six-figure severance package. Conservative Party peerLord Spicer later reported that Duncan Smith was "almost in tears" and threatened to resign if the Conservative Party board would not let him keep Legg.
