Larry Flynt, the porn tycoon and unlikely First Amendment champion, died Wednesday in Los Angeles of heart failure, according to TMZ. He was 78.

Flynt founded Hustler magazine in 1974, known for its lewd pictures and crude takes, which eventually blossomed into a full-fledged media empire. It hit early success publishing naked photos of Jacqueline Onassis in 1975, selling more than a million copies of a single issue. Flynt was jailed on obscenity and organized crime charges the following year and faced a sentence of seven to 25 years. After six days in jail and allegations of prosecutorial misconduct and a biased jury, however, he was freed. The Hustler brand also boasted strip clubs under its umbrella.

“When I started Hustler, I wanted to deal with sex as I knew it—as a boy growing up on a farm, working in a factory, on the street—four-letter words and all. That’s the approach I’ve taken, and it cost me my freedom,” he told People magazine in 1977.

The magazine’s jabs at notorious evangelical preacher Jerry Falwell wound up resulting in a landmark Supreme Court case, Hustler v. Falwell, where the court ruled unanimously that freedom of speech protections extended to intentionally offensive parodies of public figures. Flynt had satirized Falwell in a fake ad that depicted him describing his first time having sex with his mother. Flynt’s life and legal troubles would later become the subject of the 1996 film The People vs. Larry Flynt.

“To my amazement, we won,” Flynt later wrote.

In 1978, Flynt suffered a gunshot wound in Georgia while battling yet another obscenity trial. No culprit was ever found or charged, but a white supremacist later claimed responsibility for the shooting and said a photo spread of interracial pornography in Hustler had motivated him to kill Flynt.

The murder attempt left Flynt wheelchair-bound (often a gold-plated one) for the remainder of his life, but he remained provocative until the end: in 2019, Hustler sent Republican congressmen Christmas Cards depicting the assassination of then-President Donald Trump. The pornographer wrote a “final farewell to the Falwells” for The Daily Beast last year as the pastor’s sex life embroiled him in scandal and cost him his job. The two had, against all odds, become friends in the intervening years.

Flynt was born in 1942 to a sharecropper, according to The Hollywood Reporter. Divorced four times, he is survived by his wife, Elizabeth, as well as four children and several grandchildren and great-grandchildren. He is preceded in death by his daughter, Lisa.