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Following his graduation from Warwick University in 1971, Wolmar worked for Marketing, Retail Newsagent, the New Statesman, and the London Daily News. He was formerly on the staff of The Independent (1989–97) and their transport correspondent for four years from 1992, covering the Privatisation of British Rail by the Major government. He has also contributed to The Observer.
Wolmar's books and columns mainly analyse the current state of the British railway industry. He has become known as one of the most vociferous media critics of rail privatisation, in terms of the upheaval which was caused following the Hatfield train crash, the current structure of the industry and the cost to taxpayers.