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.

At that time, the city fathers and the downtown establishment had big plans to connect the Golden Gate Bridge to the Bay Bridge by running a freeway along the Embarcadero and through Golden Gate Park, something that’s unthinkable today. The Guardian successfully led the charge against that, and also campaigned against new skyscrapers in the city, or, as Brugmann put it, the “Manhattanization” of San Francisco. In 1986, after several unsuccessful tries, a Guardian-backed slow-growth ballot initiative passed, making San Francisco the first city in the country to set annual limits on high-rise office development. Brugmann also battled relentlessly on public-records issues, and as a result, San Franciscans have some of the best open-government laws in the nation.

As land-use issues dominated local politics, the Guardian’s audience grew—and so did the size and influence of the paper. Candidates’ internal polls showed that being endorsed by Brugmann’s paper was more important than getting the nod from the dailies. “I used to take their recommendations just to know what to vote against,” says Quentin Kopp, a former city supervisor and state senator from San Francisco—and a conservative, at least by San Francisco standards.

At its zenith, in the late 1990s, the Guardian weighed in at 140 pages, claimed a circulation of 155,000, and an editorial staff of 30. The good times continued until a series of blows, starting with the dot-com crash of 2000 and continuing through the Great Recession of 2008, savaged the local economy and the paper’s advertising revenue. In between, there was the slow and steady erosion of newspapers’ business model by the Web, and also a costly war with the city’s other alternative newspaper, the SF Weekly.

Founded in the mid-1980s, SF Weekly was bought in 1995 by New Times Media, which owned 10 other weeklies. In 2005, Village Voice Media merged with New Times Media, creating a publishing behemoth that turned the idea of an independent weekly on its head. (*Correction appended)

The merged papers’ economies of scale allowed the SF Weekly to cut ad rates dramatically in an effort to drive the Guardian out of business. In 2004, Brugmann sued under a state antitrust law, which prohibits a national entity from selling below cost to clear away competitors. In 2008, a jury sided with Brugmann, awarding the Guardian $21 million in damages. In 2010, the two parties settled for an undisclosed amount.

The victory did little to change the gloomy prognosis for the Guardian. Over the last year, the paper has shrunk to an average of 48 pages, circulation has dropped to 65,000, and the editorial staff is down to seven. Earlier this year, the Brugmanns started looking for a buyer. “What do you do when you reach a certain age?” Brugmann says. “The profit and the revenue just weren’t there. We couldn’t keep doing this to the staff and to ourselves.”

The San Francisco Examiner, itself rescued from extinction in December by group of Canadian investors, reportedly offered around $1 million for the weekly. Todd Vogt, leader of the investor group, has promised no editorial interference and has hired the staff in full, including Tim Redmond, Brugmann’s protégé, who has worked at the Guardian for 30 years.

There is, though, an undeniable irony to the circumstances of Brugmann’s exit, which was not lost on his various enemies: The Guardian, which will now share printing, offices, and distribution with the Examiner, is in its own version of a JOA. The SF Weekly, still smarting over Brugmann’s charge, in his lawsuit, that it was run by an out-of-touch, out-of-town corporation, wrote in an editorial announcing the sale: “Every progressive has his price. This is the foie gras of Schadenfreude. The delicious hypocrisy is so thick, it’s spreadable, yet it melts in your mouth like ice cream.” And The San Francisco Business Times noted that the $6.5-million deal for the Guardian’s building was brokered by Union Property Capital, the same company that did the planning for one of the luxury highrises that Brugmann fought bitterly a decade ago.

Meanwhile, the San Francisco that Brugmann worked so hard to prevent is gradually becoming a reality. The slow-growth initiative contained the development of commercial skyscrapers downtown, but not the construction of residential towers. His opposition to the tax breaks the city gave to George Lucas’s Industrial Light & Magic and Twitter seems almost quaint as the so-called knowledge economy gobbles up tanneries, factories, and warehouses, including those along the southeastern waterfront where the Guardian had its offices. It’s tough to sustain a working-class culture in a town where a one-bedroom apartment goes for $2,500 a month.

Yet Brugmann is not giving up—not yet, anyway. He blogs for the Guardian, where he will remain editor at large, and is active in press-freedom issues internationally. Just then, the furniture movers interrupt him and take possession of the very chair he is seated on. But he keeps talking, pledging to work to contain residential development and strengthen the open-government law, which he says has been weakened over time. “There’s a lot of work to do,” Brugmann says. “As long as you’re fighting, you haven’t lost.”

*Correction: This paragraph has been changed to reflect that SF Weekly was purchased by New Times Media in 1995, not 1999, and that the 2005 merger of New Times Media and Village Voice Media did not involve the 17 largest alt-weeklies in the country.

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