Jackson (Tito) is born in the South End.

The son of Rachel Twymon, Tito Jackson is adopted and raised by Rosa and Herb Kwakuzulu Jackson, grows up at 37 Schuyler Street, attends Brookline Schools through the METCO program, and graduates from the University of New Hampshire, where he was the first African-American student body president. He serves on the Boston City Council (2001-17) and runs unsuccessfully for mayor of Boston in 2017.