Richard Bailey and Nicole Crosby are headed to a November showdown in the race for the City Council’s District 2 seat.
Bailey, the former Republican Mayor of Coronado who moved to Point Loma and dropped his party affiliation, took 38.8% of the vote, while Crosby, a deputy city attorney endorsed by the county’s Democratic Party won 31.3%, as of early Wednesday morning. Democrat Josh Coyne was in a distant third place with 11.3%.
Bailey said he wasn’t surprised by the results as he celebrated at the San Diego County Republican Party’s watch party in the US Grant Hotel.
“[Voters] want a change at city hall,” Bailey said.
“This is going to be a very clear choice between the same failed policies and political leadership that caused the challenges faced in San Diego and a new direction.”
At the San Diego County Democratic Party’s watch party, Chair Will Rodriguez-Kennedy claimed victory as he introduced Crosby.
“This race was won by hard work,” he said.
“This race is about preserving District 2, this race is about preserving our community,” Crosby said during her victory speech.
“It’s really important for someone [to win] who actually knows what’s going on, who is not going to give misinformation about what’s happening in our community and who is here to actually listen to real San Diegans and not be supported by corporate interests, developers and gun runners” Crosby told Times of San Diego in an interview.
The race for the open seat — Councilmember Jen Campbell is termed out — was the most expensive of the city’s four council races this cycle. Seven candidates were vying for a spot in a two-candidate runoff on the November ballot.
The district covers Point Loma, Ocean Beach, Mission Beach, Bay Park and the Clairemont areas.
The candidate who wins in November will inherit a range of issues, from the Ocean Beach Pier — some residents have been frustrated with Campbell’s handling of its long-delayed repairs — to Midway Rising, a development with neighborhood impact that also has citywide implications. Vacation rentals, housing development and homelessness are all major issues in the district.
Among the field, four candidates emerged as frontrunners — Bailey, former city staffer Coyne, Crosby, and community activist Mandy Havlik — three of whom are Democrats. Bailey, a former Republican, changed his registration in February to run as an independent.
Despite his decisive first-place finish, Bailey has a tough assignment in November. Of the 87,584 District 2 votes counted so far, 61.2% went to Democrats.
Among the Democratic coalition, endorsements were primarily split between Crosby and Coyne. Crosby won support from the San Diego County Democratic Party and the San Diego and Imperial Counties Labor Council; Coyne received endorsements from high-profile elected officials and the construction union Local Laborers Local 89, which spent heavily on his behalf in the closing weeks of the race.
Coyne enjoyed the most financial support, with more than $420,000 spent on his campaign. Over $300,000 of that came from independent expenditures by Laborers Local 89.
Bailey came in second in campaign fundraising and spending, followed by Crosby and Havlick. Bailey, however, attracted all the opposition spending in the race, roughly $148,000.
Updated 12:41 a.m. June 3, 2026
