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.

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