Before 2010, San Leandro voters had never seen a city council incumbent lose re-election. With the aid of ranked-choice voting that year, San Leandro Mayor Tony Santos was upset by Stephen Cassidy. Two years ago, Councilmember Lee Thomas was narrowly defeated by Victor Aguilar. Next week, there’s a good possibility a third incumbent in the past decade could be unseated by San Leandro voters.

District 2 Councilmember Ed Hernandez is facing a strong challenge this November from Bryan Azevedo, who has long fashioned himself as a philanthropic everyman.

There are two strong similarities between the 2018 race in District 3 that included Thomas and Aguilar, and this year’s District 2 matchup. Both involve head-to-head matchups from the seat’s prior election cycle. Thomas defeated Aguilar in 2014 for the then-open seat and Hernandez defeated Azevedo in 2016.

If an upset is registered next week by Azevedo, one of the main factors will be growing opposition to a number of developments planned in the city. Specifically, the 42-unit housing project known as the 1388 Bancroft Apartments.

Aguilar stunned Thomas by using the project as a cudgel for NIMBYs worried about traffic congestion and angry over a perception the city kowtowed to the developer, Tom Silva, in order to rezone the property. The Bancroft Avenue property is nestled between a residential area and the edge of downtown San Leandro.

Azevedo is using the Silva project to the same effect over the past few months. It didn’t help Hernandez that he missed the contentious vote on the 1388 Bancroft Apartments last month, creating the perception he skipped the vote to avoid giving Azevedo more political ammunition. Hernandez later said he missed the meeting due to an illness in his family.

A victory for Azevedo will undoubtedly signal that San Leandro is in the midst of a shift toward anti-growth sentiment. The San Leandro City Council has never been known for its courageousness, so two successive upsets over a modest housing project will likely make them extremely cautious going forward.

But it’s not clear whether Azevedo is actually a NIMBY or merely a useful cypher for San Leandro NIMBYs who simultaneously fly a progressive banner. Just like four years ago, Azevedo appears woefully unprepared for the job even though he’s been campaigning for the last two years. Instead of studying policy, he’s spent time feeding residents, helping seniors during the pandemic, and other charitable acts. There’s nothing wrong with that, but his lack of an ideology could make him, if elected, a worrisome empty vessel to be filled by special interests down the line.

By the same token, Azevedo’s outreach may prove formidable come Election Day. But the type of residents he’s reaching, don’t appear to be typical San Leandro voters. As evidenced by the extreme number of Hernandez signs that have been stolen, Azevedo’s supporters don’t seem motivated by ideology but petty dislike for Hernandez, along with a hint of antigovernmental sentiment . Do these people who clutter Azevedo’s Facebook postings in droves actually vote or are they just online sycophants?

Last September when being interviewed by the Alameda County Democratic Central Committee, Azevedo shockingly could not answer any questions about San Leandro’s Measure VV, the potentially crucial Real Property Tax Transfer ballot measure. It was a telling moment that showed the candidate’s clear lack of preparedness. Yet, the central committee still endorsed his campaign.

If anything, it shows just how far Hernandez has fallen in the eyes of local Democrats, who criticize him as too moderate and often less than forthright in his dealing with them. All told, it may signal another upset in San Leandro politics.

In San Leandro’s other contested council race, Oro Loma Sanitary District Board Director Fred Simon is facing Chris Bammer. The open seat is being vacated by termed out Councilmember Benny Lee, who incidentally, is on the ballot this November for a seat on the Oro Loma board.

Most observers predict Simon will win the District 4 seat next week. Like Azevedo, Simon is a potentially raw newcomer. Unlike Azevedo, he has shown himself to be a well-prepared and studious Oro Loma board member. Going forward, the prospect of Azevedo, Simon, and the often loafing Aguilar, could make the San Leandro City Council one of the worst in Alameda County politics, at least for their first year in office.