On January 23, 2014, D'Souza was charged with making $20,000 in illegal campaign contributions to the New York Senate campaign of Wendy Long and causing false statements to be made to the Federal Election Commission.

On May 20, 2014, D'Souza pleaded guilty to one felonycount of making illegal contributions in the names of others. On September 23, 2014, the court sentenced D'Souza to five years' probation, eight months in a halfway house, and a $30,000 fine.

While D'Souza was being sentenced for campaign finance fraud in 2014, Dixie Brubaker (ex-wife) wrote a letter to the judge alleging that D'Souza had physically abused her; she claimed that "in April 2012 … he, using his purple belt karate skills, kicked me in the head and shoulder, knocking me to the ground and creating injuries that pain me to this day."