He joined the Communist Party in 1977 and held many positions within it including party organizer in Vancouver from 1978 to 1985, and leader of the party's Atlantic branch (based in Halifax) from 1986 to 1992. While leader of the Atlantic branch, Figueroa chaired an organizing committee that signed up 800 part-time seasonal professors and teaching assistants at Dalhousie University, ultimately leading to membership in the Canadian Union of Public Employees.
The collapse of the Soviet Union led to internal party weaknesses within the CPC. Under the leadership of general secretaryGeorge Hewison (1988–92), the leadership of the CPC and a segment of its general membership began to abandon Marxism-Leninism as the basis of the Party's revolutionary perspective, and ultimately moved to liquidate the Party itself, seeking to replace it with a left, social democratic entity.
The protracted ideological and political crisis created much confusion and disorientation within the ranks of the Party, and paralysed both its independent and united front work for over two years. Ultimately, the Hewison-led majority in the party's Central Committee voted to abandon Marxism-Leninism. An orthodox minority, led by Elizabeth Rowley, Figueroa and former leader William Kashtan, resisted this effort. In August 1991, evidence was revealed of the plans of the leadership to liquidate the party and seize its assets. The Hewison group reacted by expelling 14 leading members of those in opposition, suspending the Ontario Provincial Committee, and introducing 'loyalty oaths' which had to be signed by all members. As a result, they took the Communist Party to court. An out-of-court settlement resulted in the Hewison leadership relinquishing the name "Communist Party of Canada", while taking most of the old party's assets to the Cecil-Ross Society, a publishing and educational foundation previously associated with the party.
A convention was held in December 1992 in which delegates declared themselves to be the continuation of the Communist Party (thus the meeting was titled the 30th CPC Convention). Delegates rejected the changes instituted by Hewison by reaffirming the CPC as a Marxist-Leninist organization. Since most of the old party's assets were now the property of the Hewison-led Cecil Ross Society, the CPC convention decided to launch a new newspaper, the People's Voice, to replace the old Canadian Tribune. The convention elected a new central committee with Figueroa as the Party's leader.
The new party, with only a few hundred members, was much smaller than the old one and had lost a number of assets, including the party's headquarters at 24 Cecil Street in Toronto. The CPC was not in a position to run fifty candidates in the 1993 federal election, the number required to maintain official party status. As a result, the newly relaunched CPC was deregistered by Elections Canada, and its remaining assets were seized by the government. A prolonged legal battle, Figueroa v. Canada ensued, resulting in a Supreme Court of Canada ruling in 2003 that overturned a provision in the Elections Act requiring fifty candidates for official party status (the number had been increased by an act of parliament in the intervening years). Earlier in the legal battle, the party had its deregistration overturned and its seized assets restored.
Figueroa has run in five Canadian general elections and at least two provincial elections: