His wide reading and cultural interaction with other scholars as well as the township community helped to develop an individual in touch with diverse groups of people.

[4] In 1963, as the command director of the underground Umkhonto we Sizwe (MK) movement, the military wing of the ANC, he began to take part in sabotage activities in South Africa, cutting electricity pylons in the vicinity of Alice, armed with a number of devices, including a saw and an old rifle he had found buried in a garden.

[2] Masondo was arrested in 1963 and sentenced to twelve years' imprisonment on Robben Island, where he was later joined by top Rivonia trialists such as Govan Mbeki, Walter Sisulu, and Nelson Mandela.

In 1975, he registered for a BCom in statistics, but did not complete the course after losing his study privileges when he intervened to defend Walter Sisulu and Govan Mbeki in a case of alleged insubordination against a white man.

He served on numerous boards and committees in the fields of education, museums, indigenous knowledge, traditional healing, reconciliation and medicine.