The message worked. Parents from all over the city—as well as parents from the Bayview who would otherwise have sent their kids to school elsewhere—put their kids’ names in for spots at the new school. Shawn Whalen, who was then the chief of staff at San Francisco State University, and Xander Shapiro, the chief marketing officer for a startup, had children in public elementary schools that fed into well-regarded middle schools. But, liking what they heard, both listed Brown as a top choice in the lottery. Kandace ­Landake—a Bayview resident and Uber driver who wanted her children to have a better education than she’d received, and whose children were in good public schools outside the neighborhood—likewise took a chance on Brown. One third-­generation Bayview resident, whom I’ll call Lisa Green, works at a large biotech company and had been sending her daughter to private school. But she too was so enticed that she marked Brown as her first choice in the lottery, and her daughter got in.

On opening day in August of 2015, around two dozen staff members greeted the very first class. That’s when the story took an alarming turn. Newspapers reported chaos on campus. Landake was later quoted in the San Francisco Examiner: “The first day of school there were, like, multiple incidents of physical violence.” After just a month, Principal Hobson quit, and an interim took charge. In mid-October, less than two months into the first school year, a third principal came on board. According to a local newspaper, in these first few months, six other faculty members resigned. (The district disputes this figure.) In a school survey, only 16 percent of the Brown staff described the campus as safe. Parents began to pull their kids out.

By August of 2016, as Brown’s second year started, only 70 students were enrolled for 100 sixth-grade seats; few wanted to send their kids there. The school was in an enrollment death spiral.

It was hard to imagine sending our daughter to a place in such chaos. But I was also unsettled that so many people spent so much money and goodwill to do the right thing for middle schoolers, with such disastrous results. I wanted to know what had happened.

Robotics teacher James Robertson and a student. Preston Gannaway

Willie L. Brown Jr., the man himself, now occupies a penthouse office with a spectacular view of the west span of the San Francisco–Oakland Bay Bridge, which happens to be named after him. As mayor, he famously gilded San Francisco City Hall’s dome with $400,000 worth of real gold. Brown’s best-known political achievements were in real estate development. He helped spur the rise of live-work lofts during the original dotcom boom and helped to turn San Francisco’s tawdry South of Market neighborhood into a booming tech startup district. After leaving office, Brown became a lobbyist; his clients included some of the biggest developers involved in transforming San Francisco into a corporate tech hub.

Small and compact at age 84, with a genial face, Brown greeted me in his office wearing an elegant purple suit. He explained that Willie L. Brown Jr. Middle School was the second iteration of a school formerly called Willie L. Brown Jr. College Preparatory Academy—“part of a group of schools called the Dream Schools,” he said, “that were going to try to afford equal educational opportunity on almost a boutique, as-needed basis.”

To make sense of this remark, it helps to understand that San Francisco has been trying, and mostly failing, for half a century to give African American and Latino students an education comparable to that provided to white and Asian students in the city. Those efforts started in the 1970s after the success of lawsuits accusing the city of maintaining racially isolated schools in the Bayview. Attempted remedies over the years included busing and racial quotas for school assignment, but both approaches foundered, partly due to opposition from families, often white and Asian, who argued they didn’t want to send their kids across town to school. In 1978, California voters passed the state’s most infamous law: Proposition 13 severely restricted raising property taxes, and required a two-thirds majority to pass many tax measures. This gutted California’s education funding so severely that the state’s public schools, which had been ranked best in the nation in the 1950s, fell to among the worst in a few decades. (They now hover around 35th.) California currently spends less per student on public education than many low-tax states. Belying its progressive image, San Francisco spends roughly half the amount per public school student than New York City, where the cost of living is comparable.

After just a month, the first principal quit and an interim took charge. In mid-October, less than two months into the first school year, a third principal came on board.

By the early 2000s, the district’s next campaign for change was aimed at improving its most underperforming schools, aided in part by a $135,000 pledge from the Bill and Melinda Gates Foundation. The district designated some of these new schools as Dream Schools. This plan involved requiring existing teachers to reapply for their jobs, sprucing up their buildings, offering foreign-language and art classes, and requiring kids to wear uniforms. The Dream School that was eventually renamed Willie Brown College Preparatory Academy—Brown 1.0, if you will, in the Bayview—opened in 2004 (the same year Facebook was founded and Google and Salesforce held their IPOs). Six years later, Brown 1.0 had only 160 kids enrolled for 500 slots, and its standardized test scores were among the worst in the state.