What to expect when you vote in Oakland, starting in October

This is an edited transcript of Oaklandside 510. You can listen to the episode wherever you get your podcasts.

Starting in October, Oakland voters will decide a mayor’s race, three City Council seats, three competitive school board seats, and several Oakland and regional ballot measures.

To help make sense of all of it, and to explain how we’re planning to cover it between now and Nov. 3, I’m joined by two of our editors: Darwin BondGraham, our news editor, who edits our City Hall, housing, and public safety reporters, and Esther Kaplan, our deputy editor, who edits our education, transportation, and arts coverage.

— Tasneem Raja, editor-in-chief, The Oaklandside

Let’s start at the top. Who’s running for mayor?

Darwin: Mayor Barbara Lee is running for a full four-year term. She won a special election last year to fill out the two years left in Mayor Sheng Thao’s term after Thao was recalled. Now Lee is asking voters to keep her in the mayor’s seat for four more years.

She’s got three challengers who qualified for the ballot. Brenda Grisham, an East Oakland business owner and public safety advocate who led the successful recall campaign against former Alameda County District Attorney Pamela Price.

Mindy Pechenuk, an educator and activist who’s run unsuccessfully for office in Oakland before.

And Julius Robinson, who describes himself as a community investment executive.

Compared to past years, is this a crowded field?

Darwin: Actually, no. It’s a smaller field than in recent elections. In the 2025 special election, 10 people ran for mayor. Ten also ran in 2022. Our newsroom’s reporting on the candidate list points to Barbara Lee running as the incumbent for a full term as one likely reason there are only four on the ballot this year.

We’ll get into Barbara Lee’s time as mayor so far, and her reelection campaign, in more depth on this podcast soon. For now, what about City Council races?

Darwin: Three council seats are up: Districts 2, 4, and 6.

In District 2, the incumbent is Charlene Wang, who was elected in 2025. She’s facing a challenge from Democratic Socialist community organizer Nate Adams.

The District 6 seat is currently occupied by council president Kevin Jenkins. He’s being challenged by Nancy Sidebotham, a longtime Oakland resident, tax specialist, and neighborhood advocate who’s run for various seats before.

And then there’s District 4, where the incumbent, Janani Ramachandran, is running unopposed. So that race, at least, is settled.

Like the mayor’s race, this year is different in that slightly fewer people are running for council. But it’s like past years in other ways. In 2022, Kevin Jenkins faced three opponents in the D6 race, and one of them was Nancy Sidebotham. So that’s kind of a rematch.

There’s also a City Auditor race, but incumbent Michael Houston is running unopposed.

Let’s talk ballot measures. Walk us through what’s going to be on the ballot beyond the candidates.

Darwin: There are two Oakland-specific measures our reporters have been tracking closely, plus a regional transit measure.

The first is the “strong mayor” charter reform measure. This is the big one. Right now, Oakland has a hybrid form of government that’s neither a strong-mayor system, like what San Francisco has, nor a council-manager system, like most cities in California. The way power is divided right now can lead to confusion about who’s really in charge.

Barbara Lee cast a rare tie-breaking vote in June to put a measure on the ballot that would restructure the government more like a strong-mayor form. It would give the mayor veto power over legislation and the budget, and more control over day-to-day administration.

That was a really interesting vote.

Darwin: Right, the council was tied 4 to 4, and Lee doesn’t often step in to break ties like that, because she’s said it can create an appearance of division between her office and the council. But she said the current system makes it “impossible for residents to know who’s responsible when things go wrong,” so she voted yes.

We’ll certainly unpack that more in the next few weeks.

What else is on the ballot?

Darwin: There’s a foreclosure tax measure. Currently, if you sell property in Oakland, you pay a tax when the property changes hands. But that doesn’t currently apply to foreclosed properties. This measure would end that carveout.

Councilmember Charlene Wang authored it, and the council passed it onto the ballot almost unanimously. The city estimates it could bring in $4 million to $13 million a year, depending on market conditions.

One important caveat: it wouldn’t apply to smaller banks and homeowners who are themselves being foreclosed on.

It looked like Oakland voters were going to get to vote on a minimum wage ballot measure, but now that’s not happening?

Darwin: Right. A coalition called Living Wage For All submitted signatures to put a $30-an-hour minimum wage on the ballot for unincorporated parts of the county. It wouldn’t affect Oakland’s minimum wage, since Oakland sets its own.

The reason it won’t be on the ballot after all is that some of the county supervisors — David Haubert, Nate Miley, and Lena Tam — were skeptical and had a lot of questions. So they invoked a clause in the elections code that allows them to briefly hit pause and ask for a study. That delay means it won’t be on the November ballot; it’ll appear in a future election.

Esther, let’s turn to you, first on the last of the ballot measures — one you’ve been following closely since you edit our transit coverage.

Esther: Right, it’s called Connect Bay Area, a sales tax measure covering Alameda, Contra Costa, San Francisco, San Mateo, and Santa Clara counties, meant to bail out BART, AC Transit, and Muni, all of which will have to undertake deep service cuts or even close stations or lines without new funding.

It qualified for the ballot this summer after organizers turned in well over the required number of signatures. It would add a half cent to the sales tax here in Oakland.

Is that one expected to pass?

Esther: It’s genuinely uncertain. Most other Bay Area tax measures failed at the ballot in June — including Oakland’s Measure E — which has some observers wondering if voters are just tired of being asked to pay more without seeing noticeable results.

But as our transit reporter Jose Fermoso has reported, the only transit-specific tax measure on that June ballot, in Marin County, was an exception. It passed easily with 70% of the vote. And the regional transit measure hasn’t drawn the kind of organized, funded opposition that sank, for example, Measure E here in Oakland or the CEO tax in San Francisco.

What’s happening with the school board?

Esther: This might actually be the most competitive set of local races this year. Three OUSD board seats are up — Districts 2, 4, and 6 — and none of them are uncontested. Also of note: in every single race, there’s a current OUSD parent running for the first time. Districts 4 and 6 each have three candidates facing off.

Talk to us about why that matters.

Esther: In recent years, as our education reporter Ashley McBride has written, the board has only had a single parent with kids currently in Oakland schools on the board — and that affects the conversations that take place.

Right now, for example, there’s only one board member who’s an active OUSD parent: Rachel Latta, who represents District 1. She isn’t up for reelection this year. Other current board members either don’t have kids in the district anymore, or have kids who haven’t started school yet.

So what changed this year?

Esther: A few things converged. OUSD is heading into this fall with real financial pressure. The district is confronting a budget gap, restarting its search for a permanent superintendent, and trying to avoid going back into state receivership, which it only exited last year.

At the same time, there’s been a real uptick in parent organizing — new parent engagement groups, a newsletter dissecting board meetings, and this year, for the first time, an independent expenditure committee formed specifically to support parent-candidates in two of these races.

Walk us through the actual school board races.

Esther: In District 2, in central Oakland, incumbent board president Jennifer Brouhard — an ally of Superintendent Denise Saddler’s and a retired special education teacher whose kids are OUSD graduates — is being challenged by Arielle Fleisher, a Crocker Highlands parent and tech worker who has been running on fixing the district’s budget.

In District 4, in the Oakland Hills, extending down into Dimond and Laurel, incumbent Mike Hutchinson — a former afterschool teacher and firebrand on the board — faces two challengers: Kathryn Camp, a Glenview Elementary School parent, and Sylvia Williams, a longtime adult bilingual teacher and special education aide in the district.

And in District 6, which covers a chunk of East Oakland, incumbent Valarie Bachelor, a former labor organizer who is the board’s sitting vice president, is being challenged by charter school teacher Alexandra Williams and by LeAna Powell, an OUSD elementary school parent and PTA activist who’s maybe best known for filing the ethics complaint that led to the investigation of former Mayor Sheng Thao.

I know from Ashley’s reporting that low compensation for school board members is one reason parents haven’t historically run.

Esther: It is. Board pay went up this year, to $3,000 a month, up from around $900 previously. That’s the result of a state law that raised compensation limits for school boards across California.

But the parent activists Ashley’s spoken to say other obstacles are a bigger deal. Many worry about engaging with a board known for conflict and acrimony, or about entering the public eye and becoming the target of parent frustrations. Some also feel like they’ve witnessed too many years of leadership failures by the board and can’t imagine one person could make a difference.

That’s why the wave of parent candidates feels like a note of optimism.

Okay, so that’s the landscape. Now let’s talk about how we’re actually planning to cover all of this between now and Nov. 3. Darwin, what’s the approach on your end?

Darwin: Our goal isn’t just to write “meet the candidate” profiles. For each major race, Eli and Natalie are working on a feature that finds the real angle in that specific contest — what’s actually driving it, not just who’s running.

For the mayor’s race, for instance, we’re looking at whether Barbara Lee can deliver on a second term given what she’s been attacked on, and how a challenger like Brenda Grisham — who’s shown she can unseat an incumbent before — might make her case.

We’re also doing district-level stories for each council race that start from what residents themselves say are the top issues, not what we assume they care about. And we’ve got ballot measure explainers in the works for the measures we just walked through. Expect clear, short pieces on what each one would actually do, who’s for it, who’s against it, and where the money’s coming from.

And Esther, on the school board side?

Esther: Ashley’s got one story on the rise of parent candidates already out, which I highly recommend, and she’s working on individual stories on each of the three board races, where we’ll drill in on how each candidate is looking at OUSD’s budget sustainability, whether they’re open to school closures, and what their vision is for strengthening student achievement.

We’re also looking to do a story on youth voters. Oakland is one of the places where 16- and 17-year-olds can actually vote in school board elections.

And we’ve got an Oaklandside candidate forum tentatively planned for late September, where we’ll break each of the district races into separate rooms to allow for high levels of dialogue and engagement. Look out for a post soon with information on how to attend. We’re also planning to record the forum for the podcast.

Any big overarching questions hanging over this whole election that listeners should keep an ear out for?

Darwin: One we’re chewing on: why aren’t most of these council races more competitive this year? District 4 is uncontested, and several other races have relatively thin fields compared to past cycles. Is that a one-off, or a real shift in Oakland politics?

Esther: The heavy use of AI in election communications is another one we’re watching.

For listeners who want the practical details, when does voting actually start?

Darwin: Ballots go out to every registered voter starting Oct. 5. Drop boxes open the following day, Oct. 6. In-person voting centers open Oct. 31. And Election Day itself is Nov. 3.

This episode of Oaklandside 510 was produced by Mark Nieto and hosted by Tasneem Raja.

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