Squire was described in The Guardian as "a user-friendly Tory wet"[1] and in The Times as "a minister who wears pebble glasses and always looks as though he lives in a bedsit.
Squire was educated at Tiffin Grammar School, Kingston upon Thames and then qualified as a Chartered Accountant while working in a small City practice.
At the Conservative Party Conference in 1973 he was booed when he opposed a motion calling on the Government to recognise the white minority regime in Rhodesia.
Squire warned that abolition of the rating system without a widely accepted alternative to put in its place might be highly damaging.
This resulted in a stand-off and Squire threatened legal action against the government to prevent an earlier move to comprehensives.
[6] The advent of a new Conservative government in May 1979 allowed Sutton to remain as an isolated pocket of selective education and grammar schools.
Upon entering Parliament, Squire was soon established as one of the "wet" group of Conservative MPs who opposed many aspects of the economic, employment and social policies of the Thatcher government.
During the 1980s, he sponsored a successful 'freedom of information' private members bill and participated in cross-party pressure groups involved with homeless people.
[9] In 1988 Squire was the only Conservative MP to vote against Section 28, legislation which sought to prevent local authorities from promoting awareness of gay issues.
[10] He became particularly well known for his regular contributions to Capital Radio's "Party Pieces" programme and he was described in The Times diary as being "pleasingly unsycophantic".
Squire consistently expressed misgivings over the personal leadership style of Margaret Thatcher, describing her as "a good wartime leader, but ...."[7] This, combined with his status as a "dripping" or "oceanic" wet meant that promotion was slow in coming.
[13] However, his prospects suddenly improved when Major became Prime Minister in 1990 and early in 1991, he became PPS to Chris Patten MP, the Chairman of the Conservative Party.
On 14 April 1992, in the immediate aftermath of the 1992 United Kingdom general election, Squire was appointed Under Secretary of State for the Environment.
[12] His background as a council leader made him an obvious choice for this role and he appeared to work harmoniously with Michael Howard, the then Secretary of State for the Environment.
[16] "His only independent income in the first four months of his enforced leisure came when he won 20 pounds on a Sunday Times brain-teaser competition"[17] He eventually "signed on" for Job Seeker's Allowance.
In 1999, he served for a short period as a National Lottery Commissioner (salary £6,200) and he was later appointed as a schools adjudicator by the Department of Education.