From Dream(keeper) to Nightmare

This blog post is Part 1 of a multi-part series about the Dream Keeper Initiative corruption scandal.

The Dream Keeper Initiative (DKI) was supposed to be a promise. Instead, it became a scheme involving high-profile bureaucrats, non-profit executives, and elected officials that resulted in one of San Francisco’s biggest corruption scandals of this decade. 

Launched in 2021 by then-Mayor London Breed and District 10 Supervisor Shamann Walton in the wake of George Floyd’s murder, DKI redirected tens of millions from law enforcement budgets into San Francisco’s Black community. The intent was clear and noble: create lasting investments in a community that had been historically underserved and excluded.

But by 2024, DKI’s promise had imploded into scandal. What was billed as a generational investment became a case study in how San Francisco’s tangled web of City Hall and politically connected nonprofits can turn dollars earmarked for equity into grift.

What Went Wrong

At its height, Dream Keeper was moving roughly $60 million a year through City departments and nonprofits. The Human Rights Commission, a city department under the leadership of then-director Sheryl Davis, was the central hub - and the core of the rot.

Sheryl Davis used her position to personally approve contracts that benefitted people close to her - including her live-in boyfriend, James Spingola, who ran Collective Impact, a non-profit that received $7.5 million in Dream Keeper funds. Davis approved $1.5 million of that total herself while failing to disclose the personal conflict of interest. Collective Impact cracked the shell on a host of other nonprofits that were misspending DKI funds: other organizations were found to be spending taxpayer money on first-class flights, luxury chauffeurs, steakhouse dinners, and alcohol.

DKI’s unraveling started with reporting that J & J Community Resources, a low-income family services provider, was accused by the City of bilking taxpayers out of more than $100,000. The group’s leader had been caught forging invoices, double-billing the city, and submitting invoices for un-approved expenses like cigars and motorcycle rentals. The J & J scandal raised flags and concerns: could this be a pattern of financial abuse? 

In July 2024, a whistleblower report, covered by The San Francisco Standard, revealed numerous allegations against Davis herself: trips for family and friends on the city’s dime, contract-splitting to avoid oversight, a trip to Martha’s Vineyard, and generally requesting more than $50,000 in reimbursements—outspending even the airport director, who oversees a ~$1.7B budget. And it only continued to get worse from there. 

But it wasn’t just corruption - it was also blatant mismanagement of funds that should have been going toward direct community investment that instead went toward extravagant expenses. For example, SF Black Wall Street received $2.3 million from DKI, and spent more on two black-tie galas than it did on actual business grants and investments. One of its leaders even funneled administrative fees into her own LLC. Urban Ed Academy took in $1.2 million to recruit Black men to teach in San Francisco schools. The result? Just five hires locally (one of them a substitute). The rest of the placements went across the Bay in Oakland.

In September 2024, a city audit reported on by the San Francisco Chronicle revealed Davis’s department had systematically misused more than $4 million in taxpayer dollars. That same week, the Standard revealed Davis’s undisclosed romantic relationship with James Spingola. Davis resigned immediately after the Standard’s reporting. 

Nearly a week later, Mayor Breed froze Dream Keeper funding . 

The Dream Keeper Initiative became a full-blown political crisis for former Mayor Breed, particularly at a time of political vulnerability amidst an increasingly shaky re-election campaign. For Davis and Spingola, it was career-ending. For San Franciscans, it was another disappointment in a classically San Franciscan way: noble intentions, right ideas, completely botched execution - and a stark reminder that whom we choose to put in power matters. 

Stay tuned for Part 2 of our series on the Dream Keeper Initiative, where we’ll explore the key characters and exactly how they perpetuated the systems of corruption.