San Diego’s District 2 City Council Race Is a Big Test 

For several years now, the San Diego City Council has been led by nine Democrats. The mayor is a Democrat. The city attorney is also a Democrat. San Diego, once known as a comparatively conservative city, joined the ranks of big cities run exclusively by Democrats.  

City Council races are officially nonpartisan elections. But for the past 20 years, parties have polarized the San Diego electorate and marshalled resources. And feelings about President Donald Trump have further stratified voters. Yes, there’s a sizable group of voters who identify as having no party preference, but they are very hostile to Trump.  

In 2018, incumbent City Councilmember Lorie Zapf, a Republican, lost her re-election bid by a landslide.  

She had weathered no significant scandal. She was not facing a major groundswell of community opposition nor was a particularly talented or rich opponent challenging her. But she was a Republican and the Democrats and union supporters did everything they could to tie her to Trump. It worked.  

Now the same district – District 2, which represents Ocean Beach, Point Loma, Mission Bay and Clairemont – has the chance to put a non-Democrat back into the seat.  

Richard Bailey, the former mayor of Coronado, has been making the case for a year, through his engaging social media videos and in op-eds and online discourse that the city is mismanaged. He goes deep on policy and achieves what is elusive for many local leaders: He can explain things in a way people understand.  

He wants to outsource city services. He wants to rebuild the Ocean Beach Pier with a “public-private partnership” – ostensibly a restaurant or other attractions that would help foot the bill of the rebuild. He wants to cut hundreds if not thousands of city employees but hire more police officers.  

But he was a Republican until a few months ago. An active leader in the party who supported Trump. And that’s what supporters of Nicole Crosby will spend a lot of money telling residents about in coming weeks.  

Crosby used to lead the Clairemont Town Council and is a deputy city attorney. Two deputy city attorneys like her have won election to the City Council – Councilmembers Raul Campillo and Marni von Wilpert – and that mix of prosecutorial credibility and community activism helped her match Bailey in results of the primary. She has joined the chorus that the city went too far on fees, on allowing ADUs in neighborhoods and questioned but not opposed Midway Rising, much like Bailey.  

Political observers have a saying about this district: The money is in Point Loma but the votes are in Clairemont. Bailey has significant support in Point Loma. One family has demonstrated willingness to put in up to $1 million or more to support him.  

But his candidacy is a test. It’s not just about whether the district would support a candidate who voted for Trump. It is about just how low the opinion is of City Hall’s current direction. How much do they want to shake things up? Do they identify Crosby as part of the change needed or part of the problem? 

At the Politifest debate between them, we’ll focus on housing, homelessness, neighborhood infrastructure and the city budget. It will be a fascinating discussion, I guarantee it.  

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