Days before resignation, Dream Keeper Initiative director Sheryl Davis hosted swanky D.C. party

She also took two trips to Martha’s Vineyard in 2023 and 2024, where she and other Dream Keeper recipients were event sponsors

Mayor Breed, right, appointed Mawuli Tugbenyoh to serve as acting replacement for Human Rights Commission head Sheryl Davis, shown in a promotional photo for an event she sponsored and spoke at on Martha’s Vineyard in 2023.

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To nobody’s surprise this close to an election where Mayor London Breed, her dear friend, is battling to keep her job, Sheryl Davis, head of the Human Rights Commission where she also ran the Dream Keeper Initiative, has resigned (on Friday the 13th, no less). As I pointed in last week’s GBTB, when London Breed was District 5 supervisor, she asked Mayor Ed Lee to allow Davis to run programming at the Ella Hill Hutch Community Center. After a few years there, Davis was asked to be interim director of the Human Rights Commission, and soon after that she became the director. In November 2023, I called out the Dream Keeper Initiative, which took $120 million from law enforcement and created a citywide plan for “reinvesting” those millions in San Francisco’s African American community, as a pet project of Mayor Breed and Supervisor Shamann Walton ripe for grift. “A quick glance at the beneficiaries brings up numerous ‘nonprofits’ with ties to Breed and Walton, including organizations involved with the SFPUC Community Benefits pay-to-play scheme,” I wrote. A year later, my predictions came true, with many of the nonprofits I referenced caught misusing those funds on everything from cigars and bourbon to $700,000 for two Juneteenth parties.

On Sept. 12, Davis took a paid leave of absence, but she phoned it in. The day before, on Sept. 11, she presided over the Dreaming Forward “fireside chat” and reception at the luxury five-star Riggs Hotel in Washington, D.C. The event was hosted by the San Francisco Human Rights Commission, as was a seminar held from 11 a.m. to noon that same day called “Dreaming Forward: Investing in Black Culture to Advance Academic Excellence,” featuring Davis and Dream Keeper Initiative director Dr. Saidah Leatutufu-Burch.

It turns out Burch has big City Family ties as well, to District 10 supervisor Shamann Walton, co-sponsor of the Dream Keeper Initiative. Walton officiated the wedding of Leattutufu to his aide and longtime associate Percy Burch. In his opening comments, Walton made light of the fact they met “while one was the boss of the other” but said (with a “wink-wink”) that both swear the relationship started outside of work. And where did they work? At the infamous Young Community Developers while Walton was director. Not surprisingly, YCD got a nice grant from the Dream Keeper Initiative.

The D.C. events attended by Davis and Leatutufu-Burch were part of the Congressional Black Caucus Foundation’s Annual Legislative Conference (ALC), which ran from Wednesday, September 11, through Sunday, September 15. The 2024 conference, presented by Amazon, was held at the Walter E. Washington Convention Center and touted on the organization’s website as “five days of premium programming and signature events.”

One month ago, Davis attended a four-day event on Martha’s Vineyard, where she facilitated one of her Dreaming Forward seminars.

And, it turns out, that’s far from the only traveling Davis has been doing, all of it a messy mix of speaking engagements, sponsorships, and networking — mostly for herself.

Two trips to Martha’s Vineyard in two years

From Aug. 12 through 15, 2024, KAIROS, which describes itself as an organization “where leaders connect, converse and cultivate effective strategies for bringing equity and justice to scale through conscious capitalism,” held their annual event, Convening for the Culture, which their website says, “provides an opportunity for leaders of color to gather during one of the Black community’s most prominent weeks of leadership activation.” Davis, along with Leatutufu-Burch, attended the four-day event on Martha’s Vineyard, where Davis facilitated one of her Dreaming Forward seminars on Monday, Aug. 12. Not only were Davis and Leatutufu-Burch participants, the Dream Keeper Initiative, via the San Francisco Human Rights Commission, was a sponsor, as was the Booker T. Washington Community Service Center, another pet project of Mayor Breed’s that I wrote about in a September 2021 article for the Marina Times titled “Cronyism is still alive and well at City Hall.” Unsurprisingly, the center got a grant of $250,000 from the Dream Keeper Initiative. 

Also listed as a sponsor is Collective Impact, which is run by Davis’s alleged live-in romantic partner (though both deny it), James Spingola. In 2021 and 2022, Davis approved $1.5 million in contracts for Collective Impact, and apparently, he spent some of that sponsoring the KAIROS annual Convening for the Culture event on Martha’s Vineyard. Perhaps, to save taxpayers some money, Davis and Spingola pulled a Harlan Kelly and Juliet Ellis move and shared a room.

A look back at the 2023 KAIROS Convening for the Culture event, also held on Martha’s Vineyard, shows Dream Keeper Initiative, via the San Francisco Human Rights Commission, and Collective Impact, were also sponsors, which clearly brought another speaking engagement for Davis and Leatutufu-Burch (and perhaps another chance for Spingola to hang out at a fancy hotel). August 17, 2023, was billed as Night for Justice, where at 6:40 p.m., Davis and Leatutufu-Burch hosted a “fireside chat” titled “Reparations & Operationalized Racial Equity.” As I’ve said for over a year, Dream Keeper Initiative was Mayor Breed and Supervisor Walton sneaking a prereparations reparations package past taxpayers, so the subject matter is something Davis and Leatutufu-Burch know plenty about. 

The relationship between KAIROS, Davis, and Leatutufu-Burch seems to keep the pair traveling all over the country (Davis is also a member of their advisory board). In May 2024, they teamed up for “Dreaming Forward About Democracy,” presented by the KAIROS Democracy Project to chat with Clark Atlanta University students.

As a side note, Mayor Breed ducked another debate, this one scheduled for Sept. 25 and hosted by The San Francisco Standard and KGO-TV. When she bowed out of the Sept. 11 debate hosted by KCBS and the San Francisco Examiner, she told KCBS political reporter and debate co-moderator Doug Sovern, “I am the mayor of San Francisco, not just a candidate. I have to run the city and that includes meetings and everything else that I need to do.” Her campaign said, “Unlike Daniel Lurie and Mark Farrell, Mayor Breed has a job.”

Indeed, the mayor did have to work that night — work the room, that is. I discovered that rather than attend the debate, Breed mingled with the Noe Valley Democratic Club at the Valley Tavern for their September 2024 member meeting. Something tells me — perhaps the San Francisco Chronicle and San Francisco Standard doing “look here, not there!” hit pieces on frontrunner Mark Farrell — that Breed doesn’t want to be quizzed about the latest scandal in a corruption saga that has plagued her entire six-year term. It will be interesting to see whether voters are willing to ignore it this November.