Former Rep. Richard Tonry, a Louisiana Democrat who served more time in prison than he did in Congress, died Tuesday of natural causes, the Associated Press reported. He was 77.

Tonry was elected to Congress in 1976 by just a few hundred votes. A challenger, however, accused Tonry of stuffing the ballot boxes in St. Bernard Parish, a New Orleans suburb, and taking illegal campaign contributions, allegations that led to a federal inquiry and, ultimately, to Tonry’s resignation from Congress after serving only four months.

He pleded guilty to the misdemeanor charges and spent six months in prison.

Tonry made two subsequent attempts to earn a spot as an elected official and shed the negative stigma his conviction and prison stay left on his record, but was twice unsuccessful.

Tonry entered the race to fill the seat he had vacated in 1977, but came in last in the four-candidate race, according to his official Congressional biography. More than 20 years later, in 1999, he sought a St. Bernard Parish judgeship, but withdrew his candidacy before the election, the AP reported.

“If you’re going to hold a misdemeanor conviction against me after 23 years, that’s a person’s choice,” he said at the time, according to the AP. “My integrity as a lawyer has never been questioned. Anyone who has any doubts about that, just ask their own lawyers about my reputation as a lawyer.”

Tonry’s federal campaign violations were not the only legal troubles he faced during his lifetime. He was convicted in 1988 of conspiring to bribe a Chitimacha Tribe chairman in Louisiana to agree to a contract that would bring bingo parlors to the state, but was later exonerated by the 5th U.S. Circuit Court of Appeals, which ruled that the bribe was not a crime under a Louisiana bribery law, according to the AP.

Aside from his legal troubles, Tonry worked as a Jesuit seminarian and founded a law firm specializing in criminal defense cases, the AP reported.

He had a “Z” tattooed on his ankle to symbolize his fandom of the fictional character Zorro, a masked outlaw who defended the people and evaded authorities.

“I think he felt it reminded him every day to help those who couldn’t help themselves,” his son told the AP.