Today, we’re having fun and games with Richard Bailey, a candidate for District 2 of the San Diego City Council.
First, a new PAC for Bailey has just been announced. This is serious stuff. But it’s also a game. Steven Richter, a semi-retired tax attorney, is the principal officer for ‘SD Policy over Politics’, the new PAC.
Here’s Arturo Castañares’ write up about the new PAC, published April 13. Castañares is the editor at large of La Prensa.
A longtime Point Loma resident has launched a new political action committee (PAC) to support a candidate in the upcoming election for San Diego City Council, according to documents filed with the California Secretary of State last week.
Steven Richter, a semi-retired tax attorney, is the principal officer for ‘SD Policy over Politics’, a new PAC formed to support Richard Bailey, a candidate for District 2, which includes the communities of Clairemont, Midway, Mission Beach, Mission Bay Park, Old Town, Ocean Beach and Point Loma.
Richard Bailey — Last month, Bailey announced his candidacy for City Council to replace termed out Councilman Dr. Jen Campbell.
“I want to help elect someone with the right experience and vision to make things better for all San Diegans,” Richter told La Prensa San Diego in an exclusive interview in his home on Sunset Cliffs. “Richard Bailey is a city leader, a business owner in the District, and an economist with real world experience.” …
In 2024, Richter donated to a PAC run by the Lincoln Club, a non-partisan business group that supported independent candidate Larry Turner in his challenge to San Diego Mayor Todd Gloria. Gloria won 55% to 44%, but the margin was closer of any many political pundits had expected.
Richter cites the mismanagement of the City by Mayor Todd Gloria and the current City Council as the motivation to donate to campaigns of independent candidates like Bailey and Turner. “The City has been run into a financial hole by mismanagement, overspending, and lack of leadership,” Richter said. “We really need to make big changes to fix things, not just tax our residents to make up for bad decisions.”
In an interview with La Prensa San Diego during the Mayor’s race, Richter confirmed that he did not have any business interests, real estate projects, or other financial conflicts with the City of San Diego. He reiterated those points again this week. …
Richter is a retired Certified Public Accountant, an active licensed attorney, and serves as a Judge Pro Tem in San Diego Superior Court. He also serves as a Sergeant in the San Diego Police Department’s Volunteer Traffic Patrol. … Richter was a lifelong registered Democrat and became an unaffiliated voter two years ago, but he says he does not support candidates based on their partisan registration.
For more, go here.
And now for the fun.
There’s a new political parody of Bailey out there, an online effort on satire; it’s called “The Bailey Bugle” and here’s a sampling:
Richard Bailey, the former Mayor of Coronado who left office with approval ratings that could make a parking meter jealous, has reportedly set his sights across the bay. Sources close to almost everyone confirm that Bailey can’t get a real job, and after “district shopping” has set his sights on District 2 in San Diego with a platform of free parking, free trash pick-up, free ponies, and free jet-packs for commuting. He’ll promise everything. And now he lies about going from ICE Supporting January 6th Insurrectionist loving MAGA Trump Republican to “independent”. He must be smoking great stuff. Or thinking that you do. One thing is for sure – you’ll never catch Bailey at a No Kings March.
“He wore out his welcome faster than a sand dollar at a souvenir shop,” said one Coronado resident who spoke anonymously to keep Bailey’s flying monkeys from doxxing him. “Between the political mudslinging and the closed beach sewage situation, we’re not exactly rolling out the red carpet for a comeback tour. Bailey couldn’t get re-elected dogcatcher here if he tried. He’s burned the Coronado Bridge, so to speak, and is trying to now jump over it. Beware career politicians with a trail of failures.
Bailey claims to be a “fiscal conservative” but he was KICKED OUT OF San Diego Rotary because he didn’t pay his dues. You don’t want this financial failure to be anywhere NEAR San Diego City coffers. Bailey squandered hundreds of thousands of Coronado TAXPAYER dollars suing SANDAG (and losing in flames), being sued by people who thought his tree-hating “cut the hundred year old Torrey Pines down to save our plastic grass at the bowling green” was stupid (it was, and he lost there, too in court) and his all around arrogance and inability to work across the bridge that harmed the people of Coronado. Bailey loves to squander your taxpayer dollars for his petty grievances against anyone contesting his “King Richard” dictates. His claims of “fiscal responsibility” are 5-star “pants on fire” liar worthy.
Yawn, is this informative outside of partisan? I really don’t care about Bailey in D2, I doubt he’d win given he shot himself in the foot playing this as a step to Mayor. But informative discussion of city issues could be made despite the dogpile. I don’t know why you’re worried about him.
Frank I’ll try not to poke the bear too much but I’ll say this – my restating of who Richard Bailey, a Trump voting Republican Mayor of Coronado who moved to D2 within weeks (days?) of announcing he was running to represent a place he’s never lived in with an ideology completely removed from where he hung his political hat for decades, has been called lies and character assassinations by two of the biggest Bailey supporters around (including one who has now started a PAC supporting him as you see above). These two continue to say, essentially, “pay no attention to who this man has been up until 15 minutes ago”. I simply will not. Yet there’s one way we can put this all to rest!
The Rag is letting all D2 candidates have their moment on this website with a post about who they are and what they believe in. Why doesn’t Richard, who we know lurks here, come out and just say what he believes in? He has the opportunity to lay out exactly who he is, what his politics are and – importantly – who he voted for for president in 2016 – 2024. This is pretty basic stuff that all voters have not only a right to know but are interested in knowing as well! If he declines, like he did with the Voice, then why wouldn’t we believe he continues to be exactly who he has always been? If he’s not making a big statement about turning over a new leaf, then why should we believe anything he has to say? And if we can’t believe anything that he has to say, or that he’ll obviously do anything – including move to D2 and leave behind decades of Republican activism at the drop of a hat – why should we elect someone like that? And if Carol and Lisa say that I’m ineligible to ask these questions, I would love someone to ask these same questions for me. The messenger doesn’t matter but the message does.
For 10 years we’ve been told a constant stream of lies by Republicans and Trump. We’ve been told to not believe what we see. They’ve demanded we think the sky isn’t blue, that 2+2 is five and whatever else Trump and the GOP have demanded. Republican voters may be fine with eating this pile of you know what but I, and other Dems in D2, certainly are not.
Richard Bailey is a Trump loving Republican who moved to D2 to immediately run for Mayor after putting aside everything he believes at the drop of a hat. No one like that should be anywhere near elected office. And I’m wrong about all of this Richard has the opportunity to correct it himself. You all talk about transparency and being upfront with people, it’s time for Richard to do what you demand of others.
Very good points. They complain about your “lack” of transparency, and then defend Bailey, who hides behind his mantra, “Policies not politics.”
Agree. Richard needs to come out and commit to serving the full 4 year term if he’s elected to the City Council. If he doesn’t commit and then runs for mayor in 2 years, we would be better off keeping Jen Campbell who does nothing for us.
If Richard is elected and then runs for mayor consider the implications. It takes 6 months to a year, to learn any new job. Then he will spend the 2nd year campaigning for Mayor. And then D2 may need a special election to elect a new person to finish his term, which costs more money to the city. And then the new Council person needs 6 months to a year to learn the job.
So D2 really doesn’t have a person fighting for our District for 3 years.
But you did poke the bear.
Would love for your good friend Trump Republican Richard Bailey to be forthright about who he is with the people whose votes he’s asking for Carol. Please ask him to write a piece and tell us (and also feel free to tell us who he voted for in 2016 – 2024 or do you already know and could never say because it’s obviously Donald Trump)!
You all talk about transparency and being upfront with people.
And your real name? Which has been asked before.
Yeah, I do talk about being upfront with people who are running for office. Seems like a higher bar for transparency than “posting in the OB Rag comment section”. I appreciate you all care so deeply about my name and you can continue to try to let that somehow distract from the facts on the ground about MAGA Mayor Bailey!
It’s not a distraction, D2, it sheds light on your camouflage. And you talk about transparency? We know you’re voting for Mandy. But your whining is not going to influence anyone.
Frank, this is such red meat for Mandy’s sycophants. And now you have written an article by Mandy Havlik. Let me repeat my post:
I am calling on Mandy Havlik to call off her shameless attack dogs. This is no way to run a campaign by having people who hide behind labels throwing lies, generalizations, and complete character assassinations on your campaign competitors. Mandy, I know you read this platform, so you have seen these vial and defaming posts. You need to change the tone and make this a more positive, solutions-based campaign. Whether we vote for you or anyone else who is running for District 2, we all must be treated with respect and dignity, not vicious and false accusations of degradation. If this continues, I truly will doubt your ability to bring civility back to city hall. It’s in your hands, Mandy. Stop this outrageous tone and mudslinging. Voters deserve better.
The Rag has offered to publish any (within reason) 1000-word policy statement by any of the D2 candidates. Mandy is simply the first candidate to take us up on the offer. BTW, tell Richard; we’ll do the same for him.
Hi Lisa.
FYI.
As Mandy Havlik’s number one fan, I can guarantee you that Mandy does not control anyone. Mandy does not ask anyone to go against Richard Bailey. Everyone here has their own personal opinions.
Mandy is supportive of stopping the paid parking fees at Balboa Park Ballot Measures that Richard Bailey is leading.
So far no word if Richard Bailey supports Mandy’s two Ballot measures to clarify wording on Hotel taxes and the Convention Center Expansion replacement TOT to keep $200 million within San Diego, and an extra $50 million for a directed Special Tax that will need everyone’s support.
Not sure in this economic environment that I agree with adding a TOT tax. Does it have the hospitality’s buy in? This on top of the recent increase from the TOT tax increase that was just implemented by the hospitality industry to direct monies to the convention center and homeless effort. It sounds more like a quick fix. I suggest that you run this proposal by the San Diego County Taxpayers Association. They are our major consumer watchdog. I would believe you could get support if the SDCTA did their analysis first. Not AI generated information.
How will the $200 million stay in SD and what will it be used for? What is the Special Tax that you are talking about. The devil is always in the details.
Yes. The San Diego County Lodging Association (SDCLA) agrees and spoke up in favor of our Measure 1 at the 03/18/2026 Rules Committee. The SDCLA and Booking Holding, Inc. (BHI) who represent Online Travel Company (OTC) agree that we are losing our existing General Fund TOT due to failure to change wording on our Transient Occupancy Tax Ordinance (TOT). The estimate is -$125 million of our General Fund revenue being lost due to failure of leadership and understanding the easy solution of TOT Reform.
These are not Tax Increases.
These are TOT Clarification and TOT Replacement where we will be losing an additional $77 million in 9 years if a $1 Billion Convention Center Expansion does not start construction.
https://obrag.org/2026/03/new-revenue-streams-to-save-san-diegans-from-budget-cuts/
I just talked with Mark Kersey of the San Diego County Taxpayer Association (SDCTA) today at City Hall and told him we plan on submitted our two Ballot Measure for TOT Reform for his board’s review and hopefully approval through their SDCTA’s new Tax Evaluation Criteria. Mark stated he has already spoken to the San Diego County Lodging Association (SDCLA) about our Measure 1. Good news.
$125 million of our 13.75% Transient Occupancy Tax (TOT) that belongs to our General Fund is currently being legally stolen by out of state and International Online Travel Companies (OTC) due to the plain language in the TOT Ordinance created in 1964 before the internet was created. 20 Years ago the City sued the OTC to get our stolen TOT revenue paid for by visitors and lost, then appealed. 10 Years ago the California Supreme Court ruled that all San Diego has to do to get its full 13.75% TOT is to have a public vote to add “Online Travel Companies” (OTC) to the Definition of “Operator” in the Municipal Code. We are also asking the definition of “Rent” include other Hotel taxes such as untaxed Resort or Destination Fees.
Podcast of our two Ballot Measures.
tinyurl.com/20260330a
Our Measure 2 is a 4% Replacement TOT to the up to 3.25% Measure C the San Diego Convention Center Expansion. Measure C has a poison pill in the original ballot language that the TOT will cease to be collected for the Convention Center and Homeless in 9 years unless a $1 Billion Convention Center Expansion construction is started.
We are trying to get 2/3 voter approval for a Special Tax to be put into lockbox Funds, with audits, and community input with the following:
1% for Homeless.
1% for Infrastructure including new Mission Beach and Ocean Beach Lifeguard Station.
1% for the Penny for the Arts, Library, and to fund the future Balboa Park Conservancy. And,
1% for Convention Center Improvements.
Thank you, La Playa for your reply and thorough information. Good stuff.
Just one more question: if the money goes into the city’s general fund, I fear those monies will be used to plug the city’s deficit and support the bloated staffing. While this should not deter support for the measure, how can we keep a tight lid on the ‘cookie jar’
For our Measure 1 the tax clarification there is nothing we can do. The money that is being lost @ $125 million would go straight to the General Fund and can be used on excessive City salaries and pensions. But it would solved the City’s structural deficit.
However, Measure 2 is where we would get funding for specific projects and civic issues only if we get 2/3 voter approval in replacing the 3.25% Convention Center Measure C TOT with a 4% citywide TOT.
As part of Measure C, the City Council recently created separate locked Fund Balances for the revenue from the Convention Center to be spent by the Convention Center Board on 02/23/2025 as Items 201 and 202. “Creation of an Annual Allocation for the Convention Center Modernization Projects and Approval of the FY26 Itemize Budget for the Convention Center Revenue Account Under Measure C.” , and “Designation of Specific Future Convention Center Capital Improvement Projects as “Covered Projects”.”
And a seperate lockbox Fund Balances for Homeless solutions 01/13/2026 as Items 331 and S506: “Clarifying Ordinance for Measure C Approved by Voters March 2020.” And. “Amendments to the San Diego Municipal Code to Establish the Homelessness Revenue Account Citizens Oversight Committee” that includes a 7 member board who decides what homeless projects to fund.
We would use the same format as the Homeless Revenue Account for the Infrastructure Fund and the Arts, Library, and Balboa Park Fund.
Mandy and I go into detail on the Podcast on how we hope the funding can be directed for the Arts, Libraries, and the Balboa Park Conservancy, so that project funding can be prioritized by citizens instead of City staff, and none of this money can be used for the General Fund except for Libraries and Infrastructure.
tinyurl.com/20260330a
Lisa – you have acted on OB Rag as Bailey’s spokesperson and as such, this last posts says it all.
You – and by extension the candidate you are speaking for – do not seem to have the necessary demeanor or temperament to represent district 2. Maybe stop before you make him even more unlikeable?
Hey Lisa! If calling Richard a Trump Republican carpetbagger who threw away everything he believed in an hour ago for the sake of winning an election in a city he’s lived for two minutes is “throwing lies, generalizations, and complete character assassinations” and “vial and defaming posts” I’ve got good news for you! He can simply disprove everything I’m saying by either responding in these comments or accepting Frank’s invitation to write about who he is! But if he’s not (and we know he’s not) then why don’t you tell me specifically what I’m saying is “throwing lies, generalizations, and complete character assassinations.” I would love to know! And if I don’t count as an acceptable person to ask that question because you don’t have my name, I’m sure others in these comments would LOVE to ask the same questions of – Who did Richard vote for for President, why should we trust someone who is willing to throw away his political ideology at the drop of a hat and will he immediately run for mayor in 2028. Seems like a low bar for someone who is, per you all, the best we have for public service. I’m waiting on an answer Lisa!
Still sounds like a way to funnel money in, and funnel policies in, from undisclosed sources. Make Richter head of the PAC and then slide the money under the table. “Policy not politics” is not any guarantee of positive, community-endorsed policy. Emphasizing policy can mean implementing new detrimental policies. Doesn’t reassure anyone that the policies will be what D2 constituents want. Just look at City Planning’s Preservation and Progress Package A. That’s a “policy.” Policy not politics could be a wolf in sheep’s clothing. SOHO has an active lawsuit suing the City over P and P Package A. And, policy in SD is just as bad as politics these days. A better P word would be “people.” If this is an election based on what the people vote in a democratic process, what do the people want? New slogan needed. Campaign still not convincing anyone of a better future for D2.
I loved the article and agree with your sentiments.
No on Bailey
Fifth Column
Just say No
I don’t know. I kind of like him. I do like the whole policies over politics “mantra” and his videos show he gets a lot of things that current City politicians don’t. He’s better than what’s sitting downtown now.
Alright Lis- ahem, I mean “Joe” ;)
Its time to drop the glazing – we can all see that he only cares about political power.
“Policies over Politics” is the latest pivot from the right to cover up their embarrassment from the trump administration by trying to appeal to the centrists with their tails between their legs.
Tho I’m no fan of Richard Bailey because he’s exactly what everyone accuses him of, whenever his name comes in any forum popcorn sales go up.
A terrible campaign move already. The first version of this article contained a video that had been edited from the original Ocean Beach Planning Board video recording of the meeting. If you can edit the woman speaking during non-agenda public comment to the start of video, you can edit her out of the video. The full meeting recording as provided by the OBPB should have been provided for the article. Yes, she’s a woman, and has hips and breasts. Camera adds 10 pounds. The edited version originally provided by the author of the article was intentional cruelty.