After Figueroa's undergraduate studies, he moved to New Hampshire and worked as a community organizer, going door-to-door to organize Latinos regarding employment and educational issues. Following law school, Figueroa moved to Hartford and served as an Assistant Attorneys General, where he litigated day care center abuse cases and violations of environmental laws. Subsequently, he won election to the Connecticut General Assembly from Hartford's Third District. After three terms, he left the legislature to become the president and general counsel of the Puerto Rican Legal Defense and Education Fund, a national civil rights group based in New York City. After nearly a decade in New York City, he returned to Connecticut as head of Universal Health Care Foundation of Connecticut. At the foundation he oversaw the effort to pass a Connecticut universal health care bill. The legislative undertaking was successful. Governor Jodi Rell vetoed the bill; Figueroa's group organized the coalition that successfully lobbied the legislature to override the veto. A nine-member board was established and charged with coming up with a specific plan for a statewide public health insurance plan entitled SustiNet by January 2011. In January 2010, he took a leave of absence to launch his Connecticut gubernatorial campaign. Figueroa has appeared on national news programs, including The Today Show, Crossfire, The O'Reilly Factor, Fox and Telemundo. He is a former columnist for The Hartford Courant. He currently serves on the boards of the Progresso Latino Fund, Latinos for National Health Insurance, the Connecticut Public Health Association, and the Partnership for Strong Communities. The Hartford Business Journal, the region's largest business publication, named him one of its "Health Care Heroes" for his contribution to the advancement of health care in Connecticut.
2010 Connecticut gubernatorial campaign
Figueroa was attempting to win the Democratic nomination through a direct primary, skipping the traditional nominating convention. This required him to obtain the signature of 15,000 registered Democrats. If he succeeded, he would have been the first statewide candidate to force a direct primary since the option was added to state law. On May 7, Figueroa dropped out of the governor's race, citing the difficulty of raising money in a potential battle against millionaires. In July, he returned as president of Universal Health Care Foundation of Connecticut.
