This spring, San Francisco’s District 5 Supervisor campaigns will take off, continuing until the elections in November. The result of this contentious race will drastically shift the city’s Board of Supervisors and local electoral politics. Frontrunner candidates Incumbent Dean Preston and Bilal Mahmood have different ideas about how to fix District 5’s issues of housing and open-air drug use, attempting to bring life and justice into the district they call home. 

Urban is located in District 5, which covers the east half of Golden Gate Park through Haight-Ashbury, Japantown and the Western Addition, the Lower Haight and Hayes Valley and most of the Tenderloin. 

The past eight years of elections between District 5 candidates have been close. In 2016, Dean Preston lost to then-Supervisor London Breed with 48% of the vote to Breed’s 52%. 

In 2019, Preston won the election against Breed’s chosen successor, Vallie Brown, to take over as District 5 Supervisor for Breed after she was elected as mayor. The race between Brown and Preston was close, but Preston won against Brown with 55% of the votes.

Preston was re-elected in 2020 and has been serving as the District 5 Supervisor since then. Preston is a member of the Democratic Socialists of America party and one of the most progressive San Francisco district supervisors currently in office. 

Local voters and political figures predict another close race for the upcoming election. San Francisco’s Democratic County Central Committee (DCCC) Member Joe Sangirardi is expecting a tight race because of the dissatisfaction many voters feel with the district. “I think that some voters right now … don’t know why things are the way they are. A lot of voters right now are just disenfranchised and looking for a change, whatever that change might be,” he said in an interview with The Urban Legend. “I don’t know that it’s necessarily an ideological change or even just a change of the person, but I definitely think that District 5 is much more likely to flip than it would have been historically.” 

Preston has lived in District 5 for 28 years. In an interview with The Urban Legend, Preston said, “I have deep roots in the district and raising my family here and have been very actively involved in neighborhood issues, as well as citywide issues for years.”

Due to his background as a tenant attorney, advocacy for affordable housing and rent security in San Francisco have been a focal point during his time serving in city politics, in addition to district needs post-COVID. “Priorities of our work have been around preventing displacement, creating affordable housing, housing homeless people, bringing back public transportation and protecting neighborhood small businesses,” said Preston. 

In the fall of 2020, Preston successfully spearheaded Proposition I, which focuses on increasing the property tax rate for properties valued between $10 and $25 million. The bill’s overt efforts at targeting wealth inequality made it a contentious proposition. Similarly to Proposition I, in 2020 Preston also passed an eviction ban bill in San Francisco, attempting to give economic relief during COVID so residents could rely on stable housing despite shifting incomes. 

As of recently, many San Francisco politicians have directed their focus toward disproving the negative media narrative surrounding homelessness and drug use in the city. In an interview with the San Francisco Chronicle last fall, Breed discussed her success in bettering the city by increasing arrests of drug dealers and public drug users. “The difference from then and now is [that] we’re starting to see results in the work we’re doing to combat [drug use],” she said. “[That and] the fact that we have gone so far as to arrest both drug dealers and drug users … and the public is not outraged over it.” 

There is competing rhetoric over how to improve the city between moderates like Mayor Breed and Mahmood and progressives such as Preston. In an interview with Mission Local, Mahmood gave his opinion on law enforcement’s crackdowns and mass arrests considering open-air drug dealing. Emphasizing his support for this approach, he said, “Arresting fentanyl dealers and providing treatment to users is necessary to ending our open-air drug markets.” 

Answering the same question, Preston gave an opposing viewpoint. “Effectiveness should be measured by whether the crackdowns have prevented overdose fatalities, reduced street violence, and improved neighborhood conditions,” he said. “By those metrics, the crackdowns have largely failed.”

In an interview with The Urban Legend Preston said, “I think one of the challenging dynamics right now is just the backlash from conservative interests against programs that were just starting to work.” Preston used the example of an overdose prevention site in San Francisco, an effort he pushed for in 2023. 

“We should take the success of an overdose prevention site and say, ‘We should have half a dozen of these around the city. [The first one] wasn’t perfect, so let’s improve them and let’s fix more,’” said Preston. “Instead, now you have this more conservative narrative that just wants to pour all the money into arresting drug users.”

While Preston has held the seat for four years, he sees continuous issues in implementing policies he sees to be the most effective. “I think that the overall biggest challenge for those who are on the more progressive end of San Francisco politics is defending the potential of evidence-based solutions, instead of just defaulting into the kind of solutions that have failed for generations,” said Preston.

Jin Valencia-Tow, intern for District 7 Supervisor also grapples with the issue of how to combat drug use in city politics. “No one is saying that we’re not going to prosecute drug dealers, it’s just about recognizing it’s a really nuanced issue and it’s not black and white,” he said. “I think the solution to most of these issues isn’t more policing. The answer to reducing [them] is having more wraparound service centers and active resources is what we need more of.” 

In an interview with Mission Local, Mahmood criticized Preston’s style of leadership and lack of collaboration with Breed for District 5’s housing and drug use issues. “For years, our political establishment, including District 5 Supervisor Dean Preston, has been focused on dysfunctional rhetoric and blaming others for their lack of outcomes,” said Mahmood.

Regarding his openness to collaboration, Mahmood expressed that he will willingly collaborate with whoever is elected as San Francisco’s next mayor. “Getting results on housing, safety and small business requires collaborating with those we don’t always agree with, and [collaboration is] what we need to achieve results.”

Sangirardi sees this openness as advantageous for Mahmood. “Voters are looking for a change and progress in any direction,” Sangirardi said in an interview with The Urban Legend. “The fact that Bilal publicly said that he’s willing to work with the mayor means that people are probably going to be much more interested in voting [for] him.” 

Preston passionately stands by his progressive policies and sees his insistence to be a strength. “I believe it’s important to continue having a representative that is willing to stand up to the status quo, willing to push for progressive solutions and to do that unapologetically,” said Preston. 

With several of the Supervisor seats up for election, the political playing field of the Board of Supervisors is set to transform. “I think there’s definitely a lot at stake in our race,” said Preston. “If one or two [Supervisor] seats were flipped to more clearly conservative candidates, I think you’d see a pretty significant impact on the policies.”

Valencia-Tow agrees with the noted importance of this upcoming election. He said, “I definitely think this new board race in November is going to be one of the most important telling[s] of where we are or where we’re heading politically as a city.”