San Jose Leadership Goes “All In” on Fligor as Assessor Race Hits Final Holiday Stretch

SAN JOSE, Calif. — As the clock ticks down to an unusual late-December runoff election, the political weight of Northern California’s largest city has firmly shifted behind one candidate.

In a decisive move that could shape the future of property taxation in Silicon Valley, San Jose Mayor Matt Mahan and the entire City Council have endorsed Neysa Fligor for Santa Clara County Assessor. The endorsement comes as Fligor, currently the Vice Mayor of Los Altos, prepares for a final showdown against tech executive Rishi Kumar to determine who will oversee the region’s massive $700 billion assessment roll.

Here is the investigative breakdown of the race, the endorsements, and the economic stakes facing the county.

The Power Move: Why Mahan Picked Fligor

The race to succeed longtime Assessor Larry Stone—who resigned in July 2025—has been defined by a clash of philosophies: technical expertise versus populist reform. Mayor Mahan’s endorsement signals a preference for the former.

Mahan, a Democrat known for catering to a more fiscal-conservative base, cited Fligor’s pragmatic approach to governance as the deciding factor.

• The Scoop: Mahan explicitly praised Fligor for not treating taxation as a “first resort” for government problems.

• The Quote: “She knows our answer to every problem can’t be another tax or bond,” Mahan stated in a press release. “The right assessor keeps revenue stable so we can continue to fund the basic services we need without overburdening our working families.”

• The Strategy: By aligning with Fligor, San Jose leadership is betting on stability. Fligor is not just an elected official in Los Altos; she is an insider—a state-certified property tax appraiser and current employee of the Assessor’s Office who helped overhaul its outdated IT systems this year.

The Opponent: The Outsider Challenge

Standing in Fligor’s path is Rishi Kumar, a former Saratoga Councilmember and tech executive who advanced to the runoff after a crowded special election on November 4.

While Fligor runs on institutional knowledge, Kumar runs on bold, if controversial, proposals.

• The Platform: Kumar has garnered attention for suggesting significant changes, such as property tax exemptions for older adults. Critics and industry analysts have scrutinized these ideas as “lofty” and potentially outside the legal jurisdiction of a county assessor.

• The Backing: Despite lacking the assessor-specific credentials of his opponent, Kumar has secured endorsements from Cupertino Mayor Liang Fang Chao and former state Assemblymembers Kansen Chu and Nora Campos.

• The Money: Campaign finance filings reveal a stark contrast. Kumar has raised approximately $35,000 this year, with a significant portion arriving only after surviving the November primary.

The Context: Economic Headwinds

Whoever wins the December 30 runoff will not inherit a smooth operation. They will be stepping into the cockpit of an economy facing its lowest property value growth in over a decade.

The Economic Reality:

• Stalled Giants: Major developments that were expected to boost the tax roll, such as Google’s massive “Downtown West” project in San Jose, remain in limbo. Originally slated for 2023, the project has been stalled by high interest rates and corporate restructuring.

• Office Vacancy: The “hybrid work” era has left deep scars on commercial real estate. The office vacancy rate in Silicon Valley has hovered near 20% for the past two years, dragging down potential assessments and tax revenue.

Fligor has positioned herself as the “technocrat” capable of navigating this turbulence. “I will continue to identify ways to improve processes that make us more efficient and also ensure that the assessments continue to be done legally, fairly and accurately,” she told reporters.

The Variable: The “Holiday Turnout” Trap

The biggest enemy for both campaigns may not be the opposing candidate, but the calendar.

The runoff is scheduled for December 30, a date sandwiched between Christmas and New Year’s Eve. Political strategists warn that voter fatigue and holiday travel could lead to historically low participation.

• The Nov. 4 Benchmark: Turnout for the special election was 51%, a number bolstered largely by the presence of the controversial statewide Proposition 50 regarding congressional redistricting.

• The Risk: With no major statewide propositions on the December ballot to drive traffic, the assessor’s race relies entirely on local engagement.

“We’re still tabulating some checks… but we still need to raise a lot more money in order to reach voters,” Fligor admitted, acknowledging the difficulty of cutting through the holiday noise.

The Verdict: A Choice of Direction

Voters in Santa Clara County face a stark choice to close out 2025.

• Option A (Fligor): A continuation of the Larry Stone era, modernized by an insider who promises efficiency and technical competence.

• Option B (Kumar): A disruption of the status quo, led by an outsider promising relief for seniors but facing questions about the feasibility of his promises.

Early voting is already underway at the Registrar of Voters on Berger Drive. As the year ends, the Silicon Valley electorate will decide who holds the keys to the region’s property wealth.