Barney Rosset, the maverick publisher who chafed at puritanism and whose relentless challenges of obscenity laws helped overthrow the final vestiges of literary censorship in the United States, died Feb. 21 at a hospital in New York. He was 89.

The death was confirmed by his son Peter Rosset, who said his father had been undergoing a double heart valve replacement procedure.

Mr. Rosset was most identified with his work at Grove Press, the New York-based book publisher he bought in the early 1950s. For the next several decades, he helped introduce a variety of European authors to American audiences, including Samuel Beckett, Eugene Ionesco, Harold Pinter and Jean-Paul Sartre.

More often, he used his company to distribute critically acclaimed but sexually explicit books by D.H. Lawrence, Henry Miller and William S. Burroughs and engaged in a series of groundbreaking legal battles that changed the way the government interpreted the First Amendment.

Speaking of Mr. Rosset and his staff at Grove, First Amendment scholar William W. Van Alstyne of the College of William and Mary Law School said, “Their willingness to take risks at the margin of criminal law undoubtedly pushed the envelope and made a positive contribution in the Supreme Court’s gradual rethinking and evolving protection of obscenity.”

Publisher Barney Rosset with some of his favorite things in his New York loft. The First Amendment crusader died Tuesday at age 89. (ROSSET ARCHIVES/AP)

In 1959, the federal Post Office Department, the primary government enforcer of obscenity statutes at the time, seized 24 cartons of Grove’s unexpurgated edition of “Lady Chatterley’s Lover,” Lawrence’s 1928 novel about an aristocrat’s wife who has an affair with a gamekeeper.

“We decided the best thing to do was send the book through the mail so it would be seized by the post office,” Mr. Rosset told the Paris Review in 1997. “We thought this would be the best way to defend the book. The post office is a federal government agency, and if they arrest you, you go to the federal court. That way you don’t have to defend the book in some small town.”

Several months after the confiscation, a federal judge overturned the ban on the book by confirming its “literary merit” and disputing the postmaster general’s finding that it was obscene. An appeals court upheld the decision, agreeing that the novel’s depictions of sex were not prurient because of their importance to the plot.

Mr. Rosset had made “Lady Chatterley’s Lover” a test case because Lawrence, who died in 1930, had earned wide literary respect. Mr. Rosset’s ultimate goal was to publish Miller’s quasi-autobiographical “Tropic of Cancer,” first published in Paris in 1934 and filled with raunchy descriptions of the author’s purported sexual conquests.

Once “Tropic of Cancer” hit stores in 1961, a flurry of charges erupted against Grove and booksellers. In 1964, the U.S. Supreme Court agreed to review and reversed the ban against the Miller book in the same ruling.

Mr. Rosset said his court victories on those two books were merely a stepping-stone to continued efforts to confront what he saw as a prudish American society. “Who knows if the limits have been reached?” he told Time magazine in 1965. “Just because the scientists split the atom, did they sit back and say, ‘Well, that’s it’?”

His next major coup came in 1966, when the Supreme Judicial Court of Massachusetts ruled that Grove’s 1962 publication of Burroughs’s “Naked Lunch,” with its vivid depictions of homosexuality and drug use, could not be deemed obscene because it had redeeming social value.

In a 2006 essay in the academic journal Twentieth-Century Literature, English literature scholar Frederick Whiting called the storm surrounding Burroughs’s book “the last instance of complete literary censorship” in the United States.

Mr. Rosset continued to go where other distributors would not when he brought the 1967 Swedish film “I Am Curious (Yellow)” to the United States. The film was a smash hit with American audiences and brought significant revenue to Mr. Rosset, but he was unable to duplicate his success. Combined with other poor financial decisions in business and real estate, Mr. Rosset was forced to sell Grove in 1985.

One of his closest collaborators at Grove, Richard Seaver, later called him “often irascible, a control freak, most of the time manic, prone to panic attacks, reveling in unfairly pitting one so-called executive against another — his method, we surmised, of testing our mettle.”

Barnet Lee Rosset Jr. was born in Chicago on May 28, 1922. He grew up the son of an Irish Catholic mother and a Jewish father, whose fortune earned as a banker later helped cushion the future publisher’s business risks.

As a child, Mr. Rosset worshiped the bank robber John Dillinger. While attending Chicago’s progressive Francis W. Parker School, he published a newspaper he called Anti-Everything. After dropping out of a series of colleges, he served as an Army photographer in China during World War II.

In 1948, he produced the semi-documentary feature film “Strange Victory,” a scathing look at race relations that compared anti-black prejudice with Nazi Germany. Its stilted filmmaking style and heavy-handed approach drew unenthusiastic reviews. He reportedly lost $250,000 of his family’s money on the venture.

Around that time, Mr. Rosset earned a philosophy degree from the University of Chicago and one in literature from the New School. On a lark, he also bought Grove Press for $3,000. The company was named for the Greenwich Village street where it was located.Seaver

Seaver, who died in 2009, helped expose Mr. Rosset to the work of Beckett, a future Nobel laureate. In 1954, Mr. Rosset paid Beckett a $200 advance to print the play “Waiting for Godot” in America. Sales were slow until it was produced on Broadway in 1956 starring Bert Lahr and E.G. Marshall.

In 1957, Mr. Rosset launched Evergreen Review, an avant-garde literary magazine whose contributors included authors Jack Kerouac and Tom Stoppard. He printed writings by black activist Malcolm X and guerrilla fighter Ernesto “Che” Guevara, who was killed in Bolivia in 1967.

Mr. Rosset traveled to Bolivia to obtain Guevara’s diaries and subsequently published them in his magazine. Not long after, someone threw a fragmentation grenade into the Grove offices. No one was killed or injured, and the bombing remains unsolved.

Starting in the late 1960s, a confluence of factors began to undermine Mr. Rosset’s status as an icon of the left and of the publishing world. He fired several employees who had tried to unionize.

In 1970, radical feminists including Robin Morgan protested that Grove “earned millions off the basic theme of humiliating, degrading and dehumanizing women,” and they demanded a number of concessions from the company. They took over Grove’s New York office until Mr. Rosset had Seaver call the police to have them removed.

Also, Grove’s success in breaking down obscenity barriers diluted its influence as other outfits entered a market that it had previously dominated.

In 1985, Grove was bought by Ann Getty, wife of oil heir Gordon Getty, and British publisher George Weidenfeld. Mr. Rosset was fired a year later but continued to have his hand in publishing under other imprints.

He received honors for his contributions to American letters from the National Book Foundation and the PEN American Center. He was the subject of a 2008 documentary, “Obscene.” His memoir, “The Subject Is Left-Handed,” a phrase taken from his FBI file, is scheduled for publication this year by Algonquin Books.

His marriages to painter Joan Mitchell, Hannelore Eckert, Cristina Agnini and Lisa Krug ended in divorce. Survivors include his fifth wife, Astrid Myers Rosset of New York; a son from his second marriage; two children from his third marriage; a daughter from his fourth marriage; three stepchildren; and eight grandchildren.

In the late 1990s, Mr. Rosset revived Evergreen Review online, which he continued to work on into his late 80s.

“Why would I retire?” Mr. Rosset told NPR. “First of all, I have no money. I have no pension. . . . What are my options? I’m going to retire to where? That’s number one. Number two, I don’t understand the idea of retiring. I mean, that, to me, is another word for death.”