By Kate Callen
When I entered the 2024 primary for the San Diego City Council District 3 seat, I knew I had very little chance of winning. I knew the race would be financially costly and physically grueling. I dreaded the long slog of speaking at forums and knocking on doors.
But I felt compelled to do it. I was furious that D3 constituents were disrespected by their representatives. I had tried everything else: protesting, speaking out at public meetings, organizing grassroots activist groups. Running for office was the only course of action left.
I’ve read a lot about Theodore Roosevelt – his life story has the sweep of an epic novel – and his best-known quote pushed me to set aside my qualms and make the decision to run:
“It is not the critic who counts, not the man who points out how the strong man stumbles or where the doer of deeds could have done better. The credit belongs to the man who is actually in the arena … who spends himself in a worthy cause … who, if he fails, at least fails while daring greatly.”
Richard Bailey appears ready to enter the arena. If you keep up with local politics, you are hearing a lot about him. He is a pragmatic centrist who has an intriguing vision for San Diego’s future spelled out on his website, www.sandiegocomeback.com.
Bailey’s slogan is “Promoting common sense policies to help the San Diego region make a comeback.” This is hugely appealing to the legions of San Diegans who haven’t seen one bit of common sense emerge from City Hall in eons.
He wants our local government to exercise fiscal responsibility, enforce public safety laws, protect air quality, fill potholes, and perhaps most important in a city stuffed with market-rate infill, change land use laws to promote middle-class housing. These are worthy goals.
I met Bailey years ago when he was mayor of Coronado. He spoke at an Emerald Keepers event at Glorietta Bay that included a tribute to my late husband’s underwater photography. I saw instantly that Bailey was whip-smart, telegenic, and enormously likeable.
So when friends who are passionate Bailey supporters – and there are many – urge me to join them, I want to say “Yes!” But I can’t. Because he has not yet stepped into the arena.
Bailey shows every sign of being a candidate. Besides the website, he is speaking at events all around the city, some of which he pays for. There is a lot of speculation about which office he might seek – maybe the District 2 seat next year, maybe a bid for mayor in 2028.
Of course, Bailey is free to take his time to declare for a particular office. But as someone who was a candidate, I know the longer you take to pull the ripcord, the less time you have to run a successful campaign.
And once you declare, the heat is on. Your record of public statements and political activities will be scrutinized. Every campaign contribution you receive – or have ever received – will be examined. Your opponents’ supporters will show you no mercy. Your opponents’ hired guns will dig for dirt on you or just manufacture some.
The process can be hellish. But it’s the only way voters can sweep aside your sloganeering and learn who you really are, who has poured money into your candidacy (and may well expect something in return), and which past behaviors may offer insights into your character.
In a 1917 commentary that criticized President Woodrow Wilson for being too cautious, Roosevelt wrote, “Rhetoric is a poor substitute for action.” I admire Bailey’s rhetoric. But that’s not enough. I hope that before too much longer, he will take the courageous action of declaring his candidacy for office.
As soon as Bailey enters the “arena”, I have 2 questions for him. #1 Who did he vote for in the presidential campaign of 2016, and #2 Who did he vote for in the presidential campaign of 2024?
Kate I find it incredibly disingenuous and insulting to this audience to write more than 600 words about Richard Bailey and “Republican” is not one of them, which is what he PROUDLY is. Does a “centrist” go on Tucker Carlson so many times you can barely count?
Where do your values stand that you’d stump for the GOP right now? In a time when fascism, led by his party’s leader Donald Trump, is on the march you want to install one of his minions into power here? Just gross and unnecessary. If you don’t want more homes built, Mandy Havlik has made it clear both in 2022 and now that that’s her lane so why not just support the candidate that aligns with all your values?
And Frank you posted an article from Bailey before, you’ve clearly got his contact information, why not just ask him for a piece as a companion to this? If he runs for office he’ll be able to hide his party ID behind the nonpartisan nature of municipal elections just like Lori Zapf and Kevin Faulconer. I see a real opportunity for the Rag to do some journalism here to make sure voters know who this guy is and who he voted for for president as you say above. I know Frank that you’re up to the challenge and I hope you take it on, we need this kind of journalism now more than ever. It’s that important.
Sandy whoever you are, me thinks you need to reread the post. You’ve mightily jumped to conclusions with no basis. No where did Kate say she supported Bailey or was ready to “install a Trump minion into power here.
Plus you believe somehow we “don’t want more homes built”. WTF? Where did you get that? Totally not true and then you slight Mandy Havlik in the same sentence.
And since you’re ready to give us direction, let me ask, have you ever contributed to our shoestring efforts?
You throw around our names as if we’re friends, yet you hide behind an internet meme.
Ah, Sandy — or whatever your real name is — I have discovered you’re a troll, who makes comments here under various names, like Jim Hoover and OBsurf92107. Thanks for helping to keep our stats up. Even though I agree with some of your comments over time re Trump et al, I find it “incredibly disingenuous and insulting” that you keep coming on here under different names and troll either us or our commenters. You do exactly what you accused the writer of doing.
Yeesh Sandy tell us how you really feel.
Look, it is true that Frank and the Rag generally oppose housing, and yes, are more than a little hypocritical (sorry Frank) about supporting the will of the voters when it is convenient for them (Prop D) and opposing it when it is inconvenient (Measures D and C).
Having said that, personal name calling does no one any favors. I’ve been down that road myself and it is just unhealthy. You can reasonably disagree with Frank, challenge the weaknesses of his arguments, and even point out hypocrisy in pretty civil ways. But going after the guy for being “childless” and not caring about anyone under 65 is not only irrelevant but also an unfair caricature. I am sure that Frank does care about people generally. I am pretty certain he believes he is doing the right thing, even though I think his views regarding housing are wrong on the merits.
The OB Rag, for all its one-sided views on housing and outdated perspectives, does provide some degree of helpful information about local issues. Yes, it does tend to attract a handful of people who like to vent in all caps about Todd Gloria or “greedy developers” or whatever, but it also does serve as a place for those who are skeptical about changes they see happening to find like-minded people. Even though I usually roll my eyes at the stuff I read on here, I cannot deny that a sense of community is important.
Since Bailey was the mayor of Coronado, is he now a resident of San Diego??
And if he now lives in San Diego, did he move so he could eventually run for mayor of San Diego? I am always concerned with the intent of carpetbaggers.
As far as Bailey’s voting record, we typically have only a few candidates running for each open position. There have been plenty of times I’ve held my nose and voted for one candidate because I didn’t agree with the other candidate. You can hardly condemn Bailey for making a choice on the ballot, that’s our right.
A “pragmatic centrist?” Bailey is by his own words a very conservative Republican ( a word you studiously avoided). He’s been running for various offices since 2010 and only ever succeeded in the very affluent, homogeneous town of Coronado. His much ballyhooed “homeless miracle” that he touted on Tucker Carlson’s program doesn’t really hold water. And he’s trained by and been associated with “The RMNNT.” Those unfamiliar with them should look up these self-styled “Warriors of Liberty.” He has no chance of winning a mayoral general election in SD. His only hope (and I believe his entire plan) is to win a jump ball should there ever be a recall of Todd Gloria.
CG — People can change parties and philosophies — just look at Nathan Fletcher, a former Republican who became a darling of some Democrats — so don’t jump (yet) to too many conclusions. We will soon learn of his recent presidential choices. If he indeed is or has been a very recent Trump supporter, he’ll go the way of Faulconer — who was destroyed running for supervisor against Larson-Remer due to his past Trump affiliations.
The ip address associated with this “name” Joni and email address has been historically associated with Daniel ” Fast Danny Diego” Smiechowski, who I believe is again running for city council in District 2.
I read about Bailey a few years back and he seemed clearly linked to RMNNT. What I read:
https://coronadotimes.com/news/2024/10/17/what-is-the-rmnnt-and-why-are-coronado-candidates-unhappy-about-its-endorsements/
https://bradwillis.substack.com/p/the-mayor-our-schools-and-the-radical
He won’t like it one bit, but if he’s going to run for any office in SD (assuming he moves here), he’s going to have to come clean about his link to these yahoos.
Christian,
Can you tell us more about your assertion that “Bailey is, by his own words, a “very conservative Republican.”?
I can recall reading (though I can’t remember where) a recent article in which Bailey specificaly denied allegations that he’s a right-wing Christian who supports banning books from the Coronado library and that he backs the agenda of the conservative/evangelical/anti-vax church that holds worship services (on public property?) in Coronado.
I know for a fact that Bailey positions himself as a “pragmatic centrist” in his public appearances, though I agree that lots of San Diego voters (and most of our elected city officials) might think anyone who argues that our city government should significantly reduce the city workforce is not a “pragmatic centrist,” but a “traditional conservative.”
Whether a candidate voted for Trump is not a deal-breaker for me when it comes to a local election, but I do understand that it’s a definate disqualifier for some of my friends and colleagues.
I do think someone should ask Bailey if he voted for Trump, what his current registration is, and his registration history. (I will do that I attend one of his forums, or talk with, if one of you doesn’t beat me to it :) )
Paul Krueger, thanks for your reply. I took my description of him as very conservative from his own guest column to San Diego Rostra, when he ran for 77th AD. He described himself as being in a “frenzied race to claim the title of Most Conservative.”
Curiously, in an exchange between the two of us on Nextdoor, Bailey denied running in 2010. When I corrected him, he simply ignored it in his answer to me. So, right now, I don’t have a lot of confidence in his candor. Nor his track record.
The Rostra link:
https://sdrostra.com/richard-bailey-on-the-race-for-the-77th-assembly-district/amp/
Bailey was on the central committee of the San Diego Republican Party and stood with the Three Percenters- with guns- in front of our school board demanding they open during Covid ( they are separate elections). That looks extreme Republican from any angle. He was anti mask, anti Vaxx and trolled me- and other Democrat running for office here in Coronado – constantly on social media as a sitting Mayor. Who does that? He ignored our sewage crisis until it closed our beaches- and STILL denied the scientific testing – claiming our waters were safe. He is a divisive Trumper and his voting registration – Republican always- is public record. Shape shifting carpet-bagger. He is despised in Coronado for being such an incompetent bully. Go on the Coronado Happenings FB page ( which he was kicked off of) to ask around. So shape shifting only works if there’s no paper trail. His is long and ugly. Total Trumper Republican who just pushes a few unpopular SD decisions like he can waive them away. He’s about as centrist as Nick Fuentes. Oh and he has no visible means of support. More red flags than a May Day parade.
Hi Laura, thanks for your input. By chance, got a copy or link of that photo?
Your on-the-ground narrative and insights into the vacuous persona of Bailey is very helpful. I am reminded of another political chameleon, who captivated the San Diego arena for many years, while ascending the Republican ranks, in search of personal glory and little else. Pete Wilson. There once was a moderate Republican Mayor who advanced smart city planning as the future model for US cities. He brought in the best of planners and academics who designed the SD growth plan, with its concentric growth barriers, to prevent leap-frog development. It all worked well until Wilson was co-opted by the SD financial kingins, whose wealth was derived from real estate development, and the rest is history. Wilson began his national rise which finally cratered with his immersion with the Orange County Birchers. Bailey positions himself as a manager of government, as if his checklist of solutions for every problem demonstrates that governing can be handled like an AI equation. He certainly managed the Coronado Council during his tenure and refused to lead on such crucial issues as the sewage tsunami. When the demands of the IB and Coronado residents resulted in a groundswell of demands for solutions, Bailey surfaced at a pivitol beach rally for the photo op, durinf which hesought credit for recent Washington action. As you say, take the pulse of Coronado residents who witnessed Bailey’s MIA management style. Indeed, he loves to climb mountains abroad, while ducking the mountains of problems on our doorstep that require visionary leadership from arena fighters, not grandstanders with simple solutions for every problem. We have so outgrown such wanna-be’s these days.
Here’s the details on a meet and greet today with Bailey. This email when to many people, so I’m assuming anyone and everyone is invited, and can ask him about his voting history and party affiliation. I’d go and do that myself, but I’ll be at the opera at 2 pm :)
A special invitation to Meet Richard Bailey on Sunday, November 2nd – 2-4p.m.
At the home of Michelle Pius and Tom Dorosewicz
1835 Altura Place, San Diego, CA 92103
Please join us as we introduce you to Richard Bailey, who was the youngest council member and mayor of Coronado. Bailey has been very active on social media this past year, sharing important information on the state of affairs of the city and county of San Diego. He brings a lot of insight to his posts because of his previous experience as an elected government official.
This will be a special occasion to meet Bailey and ask him questions about his future political goals.
Please R.S.V.P. to “Michelle Pius”
Kudos to Kate for a great column. I, too, want to like Bailey and friends are near rabid in their own enthusiasm but the jury will remain out until he states why he would train (Awaken/RMNNT) candidates to win public office if he doesn’t share their values?
Thank You Laura. It sounds as if you know Mr. Bailey quite well.