I’m thrilled to sit down with Desiree Sainthrope, a legal expert whose deep knowledge of policy and compliance has made her a go-to voice on complex urban and economic issues. With a background in drafting trade agreements and a keen interest in the intersection of law and technology, Desiree brings a unique perspective to San Francisco’s current political debates over taxation and business policies. Today, we’ll explore the tensions between progressive tax proposals and the city’s push to attract business, the potential impacts on tenants and transit, and the delicate balance of rebranding San Francisco as a hub for innovation.
How do you see Supervisor Jackie Fielder’s concerns about Mayor Lurie’s real estate tax plan playing out for San Francisco’s tenants and landlords, especially regarding her push to prevent cost pass-throughs to rent-controlled tenants and to lift caps on big property owners?
I think Fielder’s concerns tap into a very real issue in San Francisco, where the housing crisis has long squeezed vulnerable populations. Her stance on preventing landlords from passing tax costs to rent-controlled tenants is rooted in a desire to protect those already struggling with affordability—imagine a single parent in the Mission District, barely making ends meet, suddenly facing a rent hike because of a policy loophole. If her proposal to block such pass-throughs succeeds, it could shield thousands of tenants, but it might also place a heavier burden on smaller landlords who rely on tight margins to maintain properties. On the flip side, removing caps on taxes for the largest property owners could generate significant revenue—potentially millions annually based on past city assessments—but risks alienating major real estate players who might look to invest elsewhere. I’ve seen similar policies unfold in other cities where landlords, feeling the pinch, deferred maintenance, which ultimately hurt tenants more. It’s a delicate dance, and the city would need robust enforcement to ensure protections don’t just shift the problem elsewhere.
What’s your perspective on the contrast between the labor-backed proposal to tax overpaid CEOs, which Fielder supports, and Lurie’s transit-focused real estate tax plan for the November ballot, and how might each shape San Francisco’s financial future?
The labor-backed proposal to tax high-earning CEOs, feeding into the city’s general fund, offers a populist appeal that could resonate with many San Franciscans tired of seeing wealth disparities widen. It’s a broad-stroke approach, potentially bringing in substantial revenue—think of the millions that could come from targeting top executives in tech and AI—but it lacks the specificity of Lurie’s plan, which directly ties real estate taxes to transit funding. Lurie’s measure addresses a critical need, as public transit is on the brink of a fiscal cliff, and ensuring dedicated funding could stabilize systems like Muni, which millions rely on daily. However, his plan risks being passed onto renters or small businesses, as Fielder noted, which could dampen economic recovery. I recall a case in another West Coast city where a similar CEO tax led to an exodus of smaller tech firms, not the giants, because they couldn’t absorb the hit. San Francisco’s financial future hinges on whether it can balance these revenue streams without scaring off the very industries it’s courting—either plan could work, but only with careful calibration.
How do you interpret Mayor Lurie’s reluctance to support the labor proposal on taxing high-earning executives, given his business-friendly branding, and what challenges might he face in maintaining that image?
Lurie’s hesitation makes sense when you consider his broader narrative of positioning San Francisco as a city reborn for business, especially for tech and AI sectors. Supporting a tax on executives could be seen as a direct jab at the very leaders he’s trying to woo—picture a CEO at a sleek downtown summit, hearing about this tax and questioning whether the city truly values their presence. His challenge lies in managing this perception; he’s walking a tightrope where one misstep could unravel years of outreach to deep-pocketed investors. I’ve heard whispers from business contacts that some firms are already wary of local policies perceived as punitive, and a tax like this could push them toward more welcoming locales like Austin. Beyond optics, there’s the practical issue of legal pushback—such taxes often face court challenges over fairness or jurisdiction, which could tie up city resources. Lurie’s got to weigh whether the revenue is worth the potential backlash, both in boardrooms and in public opinion.
Regarding Rafael Mandelman’s comment about additional taxes on the wealthy or companies undermining Lurie’s ‘new leaf’ narrative, how do you view this balancing act between taxing wealth and attracting business investment in San Francisco?
Mandelman’s point cuts to the heart of a perennial struggle in cities like San Francisco: how do you fund public goods without biting the hand that feeds economic growth? Taxing wealth—whether individuals or corporations—can generate vital revenue for social programs, but there’s a tipping point. I remember a policy shift a few years back in a similar urban hub where a modest increase in corporate taxes led to a 15% drop in new business registrations within two years; companies simply recalculated their bottom line and moved. Lurie’s ‘new leaf’ pitch is about signaling stability and partnership, and any whiff of hostility through taxes could disrupt that. On the other hand, ignoring wealth taxes risks alienating a progressive base that sees unchecked corporate profits as the root of inequality. It’s a messy equation—step one is transparency about where tax dollars go, step two is offering incentives like streamlined permitting to offset the sting, and step three is constant dialogue with business leaders to gauge their breaking point. Without that balance, the city could swing too far in either direction and lose ground.
Aaron Peskin’s critique about CEOs and companies like Waymo profiting off San Francisco’s streets while public transit struggles is striking—how do you see this disparity in the context of the wealth tax versus Lurie’s real estate tax, and what might the long-term effects be on transit funding?
Peskin’s frustration is palpable and grounded in a harsh reality: companies like Waymo are using public infrastructure—our streets—as their testing ground and revenue source while transit systems teeter on the edge of collapse. A wealth tax, as he seems to favor, could theoretically address this by pulling from corporate profits to bolster the general fund, some of which could trickle to transit. But without a direct pipeline, as in Lurie’s real estate tax plan, there’s no guarantee—past city budgets have shown general fund allocations often get siphoned to more urgent crises, leaving transit underfunded by as much as 30% of projected needs in some years. Lurie’s plan, while narrower, ensures transit gets the cash directly, which could mean the difference between Muni running reliably or cutting routes, impacting thousands of daily commuters who can’t afford delays. Long-term, if the wealth tax wins but isn’t earmarked, we might see transit limp along with patchwork fixes; if Lurie’s prevails, we could rebuild a robust system, but only if the tax burden doesn’t crush smaller property owners first. It’s a gamble either way, and the city’s most vulnerable riders are the ones who’ll feel the outcome most acutely.
What is your forecast for San Francisco’s ability to reconcile these competing tax proposals with its goal of economic revitalization?
I’m cautiously optimistic, but it’s going to require a level of political finesse we haven’t always seen in San Francisco. The city has the potential to blend these approaches—perhaps a hybrid tax model that targets wealth without broad punitive measures and ties some revenue directly to transit while offering business incentives. Without compromise, we risk a polarized outcome where either businesses flee or public services crumble, and neither serves the city’s long-term health. I foresee intense negotiations in the coming months, especially as the November ballot looms, and the deciding factor will be whether leaders can sell a shared vision to both progressives and corporate stakeholders. If they fail, we might see a stalled recovery, with empty storefronts and overcrowded buses as the lasting image. But if they succeed, San Francisco could become a model for balancing equity and growth—I’ll be watching closely to see which path wins out.
