Democrat With Local Roots Outshines Triple-Time Trump Voter and Carpetbagger Richard Bailey
Candidate Nicole Crosby has won the OB Rag’s endorsement for the general election to be held in 30 days. Coming to this stance, I looked at Nicole’s campaign website, my experiences over the last year with Richard Bailey, reviewed candidate debate reports from the U-T, Times of San Diego and our own Rag account.
Bailey has been campaigning for over a year and has polished off a number of campaign phrases — he’s into policies not politics, and the city doesn’t have a money problem, it has a spending problem. Yet, of course, he’s into politics.
Although not perfect, Crosby has a more compassionate heart than Bailey does when you compare their positions on San Diego’s homelessness, rent-control, city staffing,Trump’s immigration policies and the constitutional rights of all citizens in the area.
Of note are Crosby’s local roots — they particularly stand out in heavy contrast to the current District 2 officeholder, Jen Campell. Crosby and her family have lived in Clairemont for many years; she was the president of the PTA for her daughter’s school and was the chair of the Clairemont Town Council. This is also a huge contrast between her and the other candidate, Richard Bailey. Bailey — the former part-time mayor of the tiny community of Coronado – just recently moved to Point Loma so he would be eligible to run. That type of movement is often called “carpetbagging.”
Merriam-Webster defines carpet-bagging as “an outsider moving into a new area to exploit a situation or seek personal, financial, or political gain without having local connections.” A similar definition states it’s a politician who runs for office in a region where they do not live or have no prior ties, just because they think it will be easier to win. This is what Bailey has done.
Yet, setting that aside, on the issue of homelessness, Crosby believes the city is spending too much on enforcing the so-called “camping ban” and sees that as a serious waste of money and the use of police officers, that it costs more than providing housing. Bailey wants to cut city funds for homeless programs.
Crosby believes in rent control for senior citizens as a way to cut into future homeless seniors; Bailey takes a typical Republican view and doesn’t believe in rent-control at all.
On the issue of the trash fee debacle, Crosby wants to rid property tax bills of the trash fee and set up a more traditional monthly billing system. Bailey — again spouting GOP talking points — wants the city just to simply get out of the trash business and contract it out to private companies.
Taking on the city’s financial mess, Bailey wants to slash and burn through the city employee rolls to save money. Crosby calls this the San Diego DOGE effort, mimicking Trump’s and Elon Musk’s cuts early in his second administration. Crosby says Bailey wants to cut 1,000 city positions, including police officers, fire fighters, lifeguards, pot-hole fillers — and as a true Democrat, Crosby wants to save jobs and respect union agreements with the various elements of the city’s workforce. Bailey does want more cops, he says.
We’d urge Crosby to look at Todd Gloria’s multiple ranks of middle-managers; they have no contracts and appear to many to be superfluous — especially in a mismanaged city. Crosby also says it’s ridiculous to compare San Diego’s situation with that of Coronado. She wants more audits of current city leases and agreements. (Recent news reports regarding the Barnes Tennis Center and the city’s golf courses have proved her correct.) Bailey says the city already has enough audits. Crosby has distanced herself from Todd Gloria and City Hall — Bailey is the true “outsider” — although not outside the establishment (The U-T has endorsed him.)
Currently, both candidates support the coastal 30-foot-height-limit, want community planning groups to have more respect and be listened to by city officials. Both are critical of Gloria’s Complete Communities housing plan and both agree there’s not sufficient infrastructure and parking in the Midway District. Bailey is more adamant about opposing the Midway Rising project. Crosby questions the project’s ability to lay the groundwork for the necessary infrastructure. A crumbling infrastructure in the city was a big motivator for Crosby to run for office. Both are opposed to bonus density laws that overrule the 30-foot height limit.
At the most recent candidate forum in Point Loma, Crosby came out swinging against Senate Bill 79.
At another forum, the candidates debated the value of automatic license plate readers (ALPRs). Crosby doesn’t support or trust FLOCK — the company that installs and runs them. Bailey has a more nuanced view, and is generally more supportive of the license plate readers.
On the issue of utilities and SDG$E, Crosby thinks the city should plan now to have a different contract when the current one runs out.
From Crosby’s website, she wants to “rein in ruthless ADU development,” wants to stop corporate investors from buying up much of the housing stock; she wants to protect the coastline and Mission Bay. She also wants to rein in short-term vacation rentals. She’s critical of the current non-accessibility of San Diego’s public transit.
Plus Crosby wants to strengthen the Sanctuary City policies of San Diego and wants to defend the rights of women and the LGBTQ community. She was seen protesting and chanting at a recent “No Kings” demonstration in downtown San Diego. Bailey has said multiple times that he supports Trump’s immigration policies and supports ICE.
In media interviews, Bailey denied he moved to Point Loma just to run for political office, and denied he switched parties to be more acceptable to blue District 2. He also said it was wrong to shut down the OB Pier. This is curious. The pier no longer works as a pier; it came to the end of its service life and needs to be totally replaced.
When Bailey was asked about his support for Trump, he deflects. Yet, the night of the June Primary election, Bailey partied with other GOP candidates. He denies his involvement or support for the Awaken Church and its militant arm — despite clear documentation that he assisted the so-called church in training its apostles to run for political office. This raises the issue of honesty. He has not come out clearly against the church and its policies or explained or admitted his involvement.
Yet, he remains very out-spoken, articulate and has worked on his campaign delivery speeches for many a moon.
One other point: Crosby is supported by some unions; and this is a boogeyman for some D2 residents. Yet, critics use a broad brush to paint all unions as negative or corrupt or too powerful. They ignore that in San Diego, the union movement is splintered. Different unions support different candidates, especially in District 8. These critics fail to appreciate the role of labor in uplifting the working and middle-class and view all of it as some monolithic structure that outweighs all other elements of society. No one complains of the role of the Chamber of Commerce, the Lincoln Club or other business and capitalist combines that have controlled San Diego’s politics for generations — until maybe just recently.
For all of these reasons, the Rag endorses Nicole Crosby for city council, District 2.





Hey Editor-Dude!
I appreciate your well-reasoned endorsement of Nicole Crosby, though I’m personally very conflicted about which candidate will be the overall best for our city council, and, more importantly, for residents.
Richard Bailey would bring a very smart, experienced, and much-needed voice for fiscal restraint, and he strongly opposes the Miday Rising developer, as it’s proposed. (Bailey, like, many of us, support redevelopment of that area, and more housing, but don’t trust the billionaire (X25) developer (Stan Kroenke) and really doubt the city’s ability to craft a lease that won’t end up costing us for unseen liabilities while protecting Kroenke’s stake in the project. Not to mention that despicable special-interest legislation that allows Midway Rising, as proposed, to escape legitimate environmental reviews and legal challenges, if warranted.
As for labor union influence in the D 2 race, I agree, in part, with your comment that:
“These critics (of labor’s expenditures for Crosby) fail to appreciate the role of labor in uplifting the working and middle-class and view all of it as some monolithic structure that outweighs all other elements of society. No one complains of the role of the Chamber of Commerce, the Lincoln Club or other business and capitalist combines that have controlled San Diego’s politics for generations — until maybe just recently.”
I would just note that while I and others are critical of labors’ huge political clout, and the allegiance it extracts from the politicians that money elects and re-elects, I for one have been equally critical of the Chamber and the Lincoln Club.
My recent letter to the UT editor explains my position on this issue:
Re: “These are the unions, developers, and wealthy donors fueling this falls San Diego City Council races” Sept 26
“Your story highlights the outsized influence that labor unions have on our elections.
When organized labor’s money makes the difference in a campaign, the chosen candidates have an implicit debt to those unions.
Labor organizations have to date contributed at least $638,000 to city council candidates, including a game-changing $250,000 to one candidate, from the Carpenter’s Union.
It’s no coincidence that the city council’s initial approval of a greatly expanded trash collection program included the hiring of more union-represented employees.
And at council meetings — which I regularly attend — our elected representatives too often sound like they’re representing the interests of unions, not taxpayers.
Labor unions have an important role in our economy, and I was a proud union member myself.
But taxpayers’ priorities often clash with those of organized labor.
And in San Diego, the scales have tipped way too far in labor’s favor.”
Thanks Paul; you’re a treasure and your observations and writings are keen and decisive. I think it also shows our readers that the Rag is not a monolith either — the main writers have differences, yet we manage to crank out a daily online newspaper.
Here are two recent debates. I encourage everyone to watch them and decide for themselves.
Pay attention to each candidate’s experience in both the private and public sectors, the solutions they’re proposing, and how directly they’re engaging with members of the community throughout this campaign. The differences are worth seeing firsthand.
This one was hosted by the League of Women Voters on September 28, 2026
https://youtu.be/NvTgqyUQwyg
And this one was hosted by the Peninsula Community Planning Board on Thursday Oct 1, 2026
https://youtu.be/tB7rioPGEXA?feature=shared