After graduating he attended North Shore Community College, where he studied criminal justice, and the University of Massachusetts Boston, where he received a B.A.

In November 1992 he was elected as a Democrat to the Massachusetts House of Representatives for the 36th Middlesex District, and he was sworn into office in January 1993.

[3][4] On November 19, 2010, DiPaola was questioned by reporters from The Boston Globe for exploiting a state pension loophole which allowed him to file for retirement, then announce a run for re-election.

[4] The following week, DiPaola revealed that the State Ethics Commission was investigating his office over allegations that his employees were illegally raising money for his re-election.

[5] On November 27, 2010, DiPaola was found dead in a hotel in Wells, Maine, from a self-inflicted gunshot wound to the head.