SAN DIEGO — August 23, 2026
With Councilmember Jennifer Campbell termed out, San Diego’s District 2 — stretching from Clairemont and the Midway District through Ocean Beach, Mission Beach, Old Town, and Point Loma — is home to the most closely watched City Council race on the November ballot. The two finalists could hardly offer a starker contrast: Richard Bailey, the former two-term Republican mayor of Coronado who re-registered as an independent and relocated to Point Loma to run, and Nicole Crosby, a Chief Deputy City Attorney and Clairemont Town Council president backed by the county Democratic Party and its labor council.
Neither candidate has built their campaign around a traditional jobs plan in the sense of targeted industry recruitment or incentive packages. Instead, both are running on competing theories of what it takes to make San Diego functional enough to support economic activity in the first place — and their disagreement starts with the size and role of city government itself.
Bailey’s pitch centers on fiscal discipline. On election night, he told KPBS that the city has effectively “become a jobs program,” with a “very bloated” government workforce driving San Diego’s structural budget deficit. His platform calls for slashing mid-management roles, questioning affordable-housing subsidy programs he describes as unfair to taxpayers who don’t qualify for the housing they fund, and changing “the model of how government delivers services” because, in his words, City Hall “is not a good operator.” His campaign leans on his own background — a master’s degree in economics, a career in finance at a Fortune 500 company, and ownership of two small businesses in the district — as evidence he understands budgets in a way he argues the current council does not. Bailey has also touted his record on the environment, including bipartisan work to secure federal funding for the Tijuana sewage crisis.
Crosby’s pitch is built around housing affordability and city services as the foundation for economic opportunity. She supports the Midway Rising redevelopment project, which would bring roughly 2,000 units of affordable housing to district-owned land in the Midway area, and backs continued expansion of accessory dwelling units — provided new projects aren’t exploiting loopholes that distort the original intent. Her stated priorities include working with the San Diego Housing Commission to expand home-ownership opportunities, curbing corporate purchases of residential properties, and cracking down on short-term vacation rentals she argues displace long-term residents and workers. She has also pushed back on Bailey’s cost-cutting framing directly, arguing at candidate forums that the city needs more grant funding rather than blanket cuts to address its budget shortfall, a position Bailey’s campaign has criticized as avoiding hard tradeoffs.
On homelessness, the two candidates split along similarly predictable lines but with more overlap than the rhetoric might suggest. Bailey favors what he calls an accountability-first approach: enforcing existing laws consistently, using the court system to direct people toward jail or rehabilitation rather than allowing continued street encampments, and treating homelessness as partly a public-safety and emergency-services issue rather than solely a housing one. He has drawn scrutiny over his claim to have “ended homelessness” as mayor of Coronado; critics note the city’s geography largely prevented encampments from forming there in the first place, and that unhoused residents were routinely given transportation across the bridge to shelters in San Diego rather than served locally.
Crosby’s homelessness platform leans on her experience helping build the city’s first comprehensive contact-and-support program for vulnerable residents as a prosecutor. She has pledged to expand shelter beds, partner with San Diego County on behavioral health services for people struggling with substance use, and build senior housing on government-owned land, pointing to data showing that seniors on fixed incomes, hit hardest by inflation, are now the fastest-growing group entering homelessness in the city. She has also flagged an estimated 20,000 homeless children countywide, most within the city of San Diego, as a driving reason for her support of denser affordable housing near schools and services.
With the primary result mirroring the state’s own governor’s race — a single strong Republican-aligned finisher facing a fractured but numerically larger Democratic-leaning field — the outcome in November may hinge less on ideology than on which economic argument District 2 voters find more persuasive: that City Hall spends too much, or that City Hall isn’t yet doing enough.
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