Bruce B. Brugmann is a stubborn guy who sticks to his point of view, even as the world he helped build is disappearing. Fitting then to sit with him late in June in the cavernous warehouse offices of The San Francisco Bay Guardian, the alt-weekly Brugmann founded 45 years ago, as he railed against opponents past and present while members of a local dance troupe hauled away the office furniture he’d donated to them after he sold the paper to The San Francisco Examiner in May.

Gruff and imposing at 6’5”, the 77-year-old Brugmann has been shaking his fist at the powerful and privileged in San Francisco since before the Summer of Love. He battled those who would darken the city skyline with tall buildings, blocked those who wanted to yuppify the working-class neighborhoods, took on the city’s Public Utilities Commission, and made plenty of enemies along the way. Former Mayor Willie Brown, a longtime nemesis of Brugmann’s, once said, “I’d recommend first you don’t read the Guardian. Because there’s absolutely nothing accurate on any page of that particular newspaper.” Brugmann turned the insult into a poster, adorned with a not-very-flattering image of Brown, which he hands to visitors as proof of the Guardian’s masthead pledge to “Print The News And Raise Hell.”

So it was with a mixture of sorrow and, in some quarters, relief, that San Franciscans learned that Brugmann and his wife and associate publisher, Jean Dibble, would be stepping aside—an acknowledgement that Brugmann’s time has passed, along with the heyday of the alternative weekly.

Not long after Brugmann launched the Guardian in 1966, about a decade after The Village Voice kicked off the alt-weekly era, nearly every big city had a scrappy weekly that offered a mix of rock & roll, liberal politics, and investigative reporting. Alt-weeklies now suffer from the same afflictions that are undercutting the dailies, only more so. Their circulation and ad revenue is tanking, and they have been largely supplanted by Twitter, blogs, and digital startups. Who needs one thorn in the side of the establishment when everyone can be a thorn? This is particularly true in the Bay Area, where a variety of digital newsrooms offer investigative reporting and diverse critical voices.

Regardless of whether you agree with Brugmann’s style or his stands, there was a swagger about him that definitely will be missed. It’s hard to imagine another San Francisco newspaper mounting an advertising campaign like the one Brugmann ran more than a decade ago that featured his bearded grimace on buses and billboards commanding, “Read my paper. Dammit.”

Born in Rock Rapids, IA, Brugmann went to the University of Nebraska hoping to be a hoops star, but wound up at the student newspaper. He met Jean, his future wife, as an undergraduate, and together they hatched the idea of someday publishing a weekly. Brugmann says he was impressed that The Daily Nebraskan, which only came out three times a week, still managed to upset the university power brokers.

In 1963, after a stint in the Army and a few years bouncing around the daily-newspaper world, Brugmann married Jean. Three years later, they had scraped together $43,000 and, on October 27, 1966, published the first issue of the Guardian, “a fortnightly journal of news, analysis and opinion.”

San Francisco newspapers at that time were struggling. In 1959, the city had three dailies, one morning and two afternoon. By the time the Guardian appeared, only the Examiner and The San Francisco Chronicle remained, and the Examiner claimed to be fading fast. In 1965, the Justice Department and the publishers had negotiated a Joint Operating Agreement to keep the city a two-newspaper town. The rivals would stay separate editorially, but share advertising, printing, and distribution, splitting the profits 50-50.

Brugmann was livid then and remains so, reciting his indictment to me as the dancers moved about us, unfazed: The JOA, he said, was “a government-protected monopoly in perpetuity that allowed them to fix prices, pool profits, and share markets so no one could compete.” He sued, and in 1975, the papers paid the Guardian $500,000 to settle. Brugmann used the money to start publishing weekly.

Danelle Morton is the co-author of 11 nonfiction books.