East Bay's June Primary Election Preview, Part 2
Oakland eyes contentious business tax ballot measure for November
—PART 2—In Thursday’s newsletter, I broke down the Alameda County District Attorney and supervisorial race in District 3, along with the 10th State Senate District campaign. Read Part 1 HERE. Part 2 of the June primary races you need to watch:
20TH ASSEMBLY DISTRICT
CANDIDATES—There’s considerable talk that this field of five candidates should be stronger. Assemblymember Bill Quirk announced last December that he would not seek re-election. The timeframe for candidates was short, but Quirk’s retirement has been talked about every cycle since 2018. Why should more candidates be interested in this seat? It’s because in the deep blue 20th District, the winner of this race will hold the seat for the next 12 years, if they desire. The contrarian position, meanwhile, is that no bench of qualified candidates exists in this district. Among the four candidates—three Democrats, one Republican—only Dublin Councilmember Shawn Kumagai has held elected office. Liz Ortega-Toro comes close. She leads the powerful Alameda Labor Council. Registered Nurse Jennifer Esteen has toiled at the grassroots and serves on the Alameda Health System board and an advisory committee in the unincorporated areas. Republican Joe Grcar ran for the 20th District in 2018 as a write-in candidate and has served on the Alameda County Republican Party.
STORYLINE—Ortega-Toro, Kumagai, and Esteen all have allegiances to union labor. Anyone of them would suit voters who support the labor movement. But Ortega-Toro has the leg up due to her work with the Alameda Labor Council. We all saw last weekend how they came out for her campaign kickoff in San Leandro. But there is concern—perhaps cynicism—that Ortega-Toro’s labor support is a mile wide and an inch deep. Voters in the 20th District should be prepared for an onslaught of mailers in support of Ortega-Toro over the next three months. Expect Kumagai to continue highlighting his experience as a public official. Watch out for Esteen, who has caught the eye of some insiders for her sheer tenacity. Esteen and her team has been pounding the pavement and doing the work door-to-door for months. Like the scenario in the 10th State Senate District, Grcar, the lone GOPer, could play havoc for Democrats eyeing a 1-2 finish on June 7.
FRONTRUNNER—More than any of these June races, the top-two is truly a toss-up. There is a sense that Ortega-Toro finishes first in a close race. If its really close among the three Democrats, then Grcar and his Republican monolith of voters, could sneak into second. But there’s so many variables here. Does the Tri-Valley come through for Kumagai? First there was Eric Swalwell, then David Haubert. A Kumagai win will solidify a power shift in the county toward the Tri-Valley. The betting line says Ortega-Toro and Kumagai in November, but keep an eye out for Esteen sneaking into the top two. But, seriously, this race could go any way.
ALAMEDA COUNTY SHERIFF
CANDIDATES—It’s this simple. If you’re a progressive in Alameda County you loath Sheriff Greg Ahern. To this group, he’s the epitome of Donald Trump in the county, and much worse. Ahern has big-time baggage. He lacks charisma and warmth and those attributes don’t help when there’s misconduct within his ranks and deaths at his prison. Yet Ahern persists. Two challengers—Yesenia Sanchez and JoAnn Walker—represent progressives’ hopes this June. Sanchez is a commander at Santa Rita Jail in Dublin. Ahern is her superior. The jail’s misconduct, however, isn’t tied to Sanchez. Walker has a background in law enforcement and training and has been the most vocal critic of Ahern in this race.
STORYLINE—Ahern has a massive fundraising advantage and it will likely grow even larger when a new round of campaign finance reports are released soon. Ahern is certainly capitalizing on the county’s staggering $40,000 individual campaign fundraising maximum. In a countywide race, Ahern’s war chest, by itself, might just overwhelmed his challengers. Sanchez is slowly gaining support from progressives and, most importantly, labor. She reportedly has the backing of the Alameda County Building Trades. That’s a major shot in the arm. Unlike Walker, who has thrown some bombs at Ahern in this race, Sanchez has taken a measured approach. It remains to be seen whether we start seeing negative ads against Ahern soon.
FRONTRUNNER—Far and away, it’s Ahern. He is not a politician, but the lack of direct contact between these candidates favors Ahern and hides his inexperience on the stump. I’m sure he could be baited by his opponents into a raging quip, but when will that happen? The way this race is going, Ahern may not even have to employ any negative messaging. Instead, he could rely solely on mailers that highlight his accomplishments as sheriff. For certain, Sanchez and Walker are hoping for a November runoff. Can they block Ahern from a simple majority on June 7? Most doubt it at this point, but it’s possible. Ahern has a rash of negatives and many still fester. Sanchez and Walker have to be praying yet another scandal involving Ahern’s sheriff’s department blows up between now and early May. Even in a November runoff, Ahern is a strong favorite for re-election, but for the second-place finisher at least it’s a second bite at the apple.
PART 3: MONDAY - 24TH ASSEMBLY DISTRICT | ALAMEDA COUNTY SUPERINTENDENT | CONGRESS/LEGISLATURE | BALLOT MEASURES

—ENDORSEMENT—Alameda County sheriff candidate Yesenia Sanchez’s bid to unseat Sheriff Greg Ahern received the support of progressive Emeryville Mayor John Bauters on Friday. “Emeryville needs a collaborative Sheriff who will work with our local police department to lead with Alameda County values,” Bauters said. The endorsement comes as Sanchez has struggled to energized the county’s progressives, despite their strong dislike of Ahern and his tenure as sheriff.
—MONEYBALL—There was a small pot of gold on St. Patrick’s Day for some candidates. Alameda County District 3 supervisorial candidate Rebecca Kaplan picked up $1,500, according to campaign finance reports, from Signature Development Group, the major Oakland developer also behind Brooklyn Basin… Alameda County DA candidate Pamela Price received three separate 1,000 contributions on Thursday from D.C. political consultant Megan Hull, attorney Deborah Schweizer, and Jillian Bauer… Seth Steward, another candidate for Alameda County DA, reported a $1,000 contribution from psychologist Jennifer Harrison on Thursday.
CITY NEWS
OAKLAND
—BIZ TAX MEASURE COMING—Oakland City Council President Nikki Fortunato Bas and Councilmember Carroll Fife introduced a plan on Friday that would ask voters this November to approve a ballot measure to raise taxes on the highest-earning Oakland businesses. The restructuring of Oakland’s flat-rate business tax would raised up to $40 million annual in new taxes to be used to expand services for the homeless, streets, and tax relief.
—The proposal, which will come to the Oakland City Council Rules and Legislation Committee on Mar. 31, has already been panned by the Oakland Metropolitan Chamber of Commerce. In an opinion piece for the San Francisco Chronicle, the Chamber’s CEO Barbara Leslie, wrote the proposed measure will hamper businesses still struggling to survive the pandemic. “What small businesses need is business — patrons buying food, clothing, gifts, hotel rooms, groceries, etc,” Leslie wrote
—Around 93 percent of Oakland businesses do not earn more than $1 million a year in gross receipts, according to Bas and Fife, and a disproportionately higher percentage of taxes. Meanwhile, higher earning Oakland businesses pay a smaller portion of tax compared to their gross receipts. Oakland, and other East Bay cities, have until the first week of August to finalize potential ballot measures for the November General Election.
D.C. DISH
17TH CONGRESSIONAL DISTRICT
—RO FOR PREZ—Progressive champion Sen. Bernie Sanders, or, at least, his surrogates, think Fremont and South Bay Rep. Ro Khanna should run for president if President Biden does not seek a second term. If not 2024, then 2028, they told Politico on Thursday.
—For what it’s worth, Khanna running for president is not what I’m hearing in the East Bay. After Rep. Eric Swalwell’s ill-fated run for president in 2020, talk about running for president elicits eyerolls in the East Bay. In the Tuesday newsletter I wrote about chatter that Khanna is eyeing a position in Biden’s administration. Based on his interaction this week with Ukraine’s consul general, it might be a position related to foreign policy.
—Khanna has a good rapport with the press and has slyly pushed these kind of stories before. Recall in early January that a Washington Post piece appeared to be a vehicle for Khanna to float interest in becoming House speaker. The same scenario was used for Khanna’s interest in the U.S. Senate in the event Feinstein steps down.
PODCAST

—EPISODE 45—Coming this weekend, it’s a baseball and politics edition of the East Bay Insiders podcast. Oakland Mayor Libby Schaaf sat down for an interview. We chatted about Howard Terminal and she offered some surprising comments about the city’s upcoming fall elections. Also, special guest Casey Pratt, ABC7 sports anchor and producer, talked with Shawn Wilson and I about the A’s ballpark situation, along with some baseball and March Madness talk.