- Joined the reform party of Canada in 1990, and was an adviser for Preston Manning until being fired in 1993
- Tom Flanagan and Stephen Harper began publishing together in 1996-7 with “Canadian conservatism is at its strongest level in many years” and their controversial opinion piece entitled “Our Benign Dictatorship: Canada’s system of one-party-plus rule has stunted democracy.
- Flanagan was a key player in Stephen Harper’s political rise to Prime Minister of Canada. Flanagan managed his leadership campaigns for the Canadian Alliance (2002) and the Conservative Party of Canada (2004).
- He also managed the Conservative Party’s national election campaign in 2004.
- He was the Senior Communications Adviser for the Conservatives successful 2005–2006 election campaign.
- In 2008, Flanagan was accused by Dona Cadman of offering her late husband, MP Chuck Cadman, a million-dollar life insurance policy (on behalf of the Conservative Party of Canada) in exchange for his vote against the Liberal budget in May 2005.
Read more about that story:HERE
- In 2010, While appearing on the CBC television program “Power & Politics”, he called for WikiLeaks founder Julian Assange to be killed. “I think Assange should be assassinated,”