[3][4] He graduated from Dalhousie Law School and was admitted to the Nova Scotia Barristers' Society in 1954.
He became one of the region's best known labour lawyers, and his high-profile image led to an invitation to enter politics.
Regan entered the Nova Scotia House of Assembly in 1967, and aggressively pursued the government of Premier George Isaac Smith as Leader of the opposition.
Regan led a fourteen-hour filibuster against the government's plans to increase the sales tax in 1969.
His government was defeated by John Buchanan's Progressive Conservative Party in the 1978 general election, in part due to the oil shock's effect on the economy.
[7][8] As of April 2, 1998, there were eighteen charges, but nine were stayed by Justice J. Michael MacDonald of the Supreme Court of Nova Scotia.