In the 1960's, Jaan was involved in various grassroots movements, ranging from the peace movement, anti-racist struggles to the labor organizing. During this time, he joined the Students for a Democratic Society (SDS), where he worked side by side with Black Panther Party and Young Lords organizing the youth. Due to a combination of government repression and slow progress of the movements of change, Jaan joined up with the underground revolutionary movement.
On January 16, 1972, a group calling itself the People's Liberation Army in New Hampshire planted four bombs in various locations in Manchester, New Hampshire. Three of the bombs exploded shattering the windows of police and fire headquarters. The fourth device was found unexploded in the police chief's office.
Jaan Laaman and another person, Anne Holt, were arrested and charged with the attacks. The Justice Department stated they found a letter on one of the arrested claiming responsibility for the action. Jaan was subsequently sentenced to 20 years in prison. After winning an appeal and getting some of his sentence reduced, he was released in 1978.
Jaan quickly stepped back into the political life and in 1979 he and his comrade Kazi Toure helped to organize the Amandla Festival of Unity. This concert, which featured Bob Marley, helped to fight racism in Boston, where it was held, and raised money to send to freedom fighters in South Africa. This activity along with the anti-racist and community security work he was doing led to increased police and Klan harassment, so Jaan, once again, went underground and joined the armed clandestine movement.
Jaan joined up with a group known as the United Freedom Front, which consisted of former members of the Sam Melville-Jonathan Jackson and other revolutionaries. The group targeted government institutions and major corporations that had ties to the South African Apartheid system or right-wing paramilitaries in Central America. This included taking actions directly against the South African and United States governments, attacking various government buildings.
The UFF continued their activities for several years, funding their actions through bank expropriations. The on February 7, 1982, Jaan Laaman and another UFF member, Kazi Toure, were involved in a shoot out with police. While Jaan managed to escape, Kazi was arrested. Despite the arrest, the group continued their operations but on November 4, 1984, five members of the group, including Jaan Laaman were arrested. Nearly six months later, the last two remaining members were arrested.
Members of the group were charged with various crimes from murder, firefights with government forces, seditious conspiracy to weapons charges. Jaan Laaman was sentenced to 98 years in prison. Recently, Jaan completed his federal sentence and was transferred to the state of Massachusetts, where he serving time for his state charges.