As a lawyer, LeDrew served as the Executive Assistant to the Solicitor General of Canada, Government Affairs Counsel for Manulife, and Director of Operations in the Prime Minister's Office.

Occasionally outspoken, he famously derided the Chrétien government's plan to severely limit corporate donations to political parties as being as "dumb as a bag of hammers".

[3] On September 28, 2006, immediately prior to nomination cut-off date, LeDrew announced his candidacy for Mayor of Toronto in that year's municipal election against incumbent David Miller, centre-right challenger Jane Pitfield and a host of fringe candidates.

Although he received considerable media coverage and was invited to participate in election debates with Miller and Pitfield, LeDrew finished a distant third with only 1.3% of the vote.

From 2007 until 2009, LeDrew co-hosted a talk show with Michael Coren on CFRB 1010 in Toronto titled Two Bald Guys With Strong Opinions.