Boland was elected to the United States House of Representatives as a Democrat in 1952. Boland's most famous work as a Congressman was the 1982 Boland Amendment, which blocked further funding of the Contras in Nicaragua after the Central Intelligence Agency had supervised acts of sabotage without notifying Congress. Boland lived in a Washington apartment with Tip O'Neill (whose wife remained in Massachusetts) until 1977 and he married at the age of 62, fathering four children. Boland retired from the House in 1989. Boland died in 2001 at the age of 90 from natural causes.