The former mayor of Oakland is under investigation for allegedly leading a political committee that attacked a rival

The Oakland Political Supervisor’s Office has announced it is investigating a second case involving an unnamed elected official who is accused of secretly running a political action committee that illegally raised large sums of money to influence an election.

The first case, which we reported on in March, involves an unnamed city official who allegedly led a committee that raised $1.8 million to support the passage of Measure AA, also known as the Oakland Children’s Initiative. According to investigators with the Oakland Public Ethics Commission, that elected official kept his involvement in the committee’s work secret from the public, violating a law designed to prevent such committees from raising money from city contractors. Although the Ethics Commission did not name the official, referring to him only as “Candidate A,” The Oaklandside was able to confirm that the person under investigation is Libby Schaaf.

The second case, recently uncovered by the Ethics Commission when it released an agenda for its June 12 meeting, involves another political action committee called the Committee for an Affordable East Bay. That group was active in the 2020 election. Investigators allege that ride-hailing giant Lyft violated city law by donating $100,000 to the committee. On paper, the committee was run by several housing activists affiliated with local YIMBY groups. But investigators believe the committee was secretly controlled by an elected official they refer to only as “Candidate A.” The Public Ethics Commission will decide this week whether to fine Lyft $50,000 for helping to fund a committee secretly controlled by Candidate A.

Just as in the first case involving the committee that supported Measure AA in 2022, commission investigators wrote in the proposed settlement with Lyft that they are withholding Candidate A’s name due to other pending cases.

The Oaklandside was able to obtain confidential investigative documents that identify Libby Schaaf as the elected official accused of secretly controlling both the Measure AA committee and the Committee for an Affordable East Bay. The documents describe Schaaf’s actions as “part of a pattern,” suggesting that a third investigation is underway accusing Schaaf of secretly controlling a committee that helped oust Councilmember Desley Brooks in the 2018 election.

Schaaf is currently running for the office of Treasurer of the State of California. The Ethics Commission has not yet accused her of any wrongdoing.

The Oaklandside attempted to reach Schaaf by phone and left two voicemails. We also sent Schaaf several emails, including messages to the address listed as the primary contact on her campaign website for the Treasury. After not hearing from her for over a week, we left a message at her home describing the Ethics Commission’s investigation and asking her to contact us. Schaaf has not responded to our multiple attempts to interview her.

The Ethics Commission treats its cases with the utmost confidentiality. It also provides information about who it is investigating and what the exact allegations are. Oaklandside was able to obtain documents about the Commission’s ongoing proceedings against Schaaf from another source.

The Commission’s lead investigator, Simon Russell, declined to comment on the details of the cases and only offered to speak generally about the Commission’s work.

Lyft reaches agreement without admitting wrongdoing

In the Lyft case, investigators say Candidate A personally asked for the company’s $100,000 donation but did not disclose that she headed the committee. At the time of the donation, Lyft was negotiating with city officials over its contract to operate a bike-sharing service in Oakland.

According to city documents, Lyft employees and lobbyists discussed e-bike rental prices, bike-share station locations and operations in the early days of the pandemic with Schaaf’s office and the city’s Department of Transportation in 2020. The year before, Schaaf announced a partnership with Lyft in which the company would donate $700,000 to help Oakland expand transportation options in low-income neighborhoods.

Under the terms of the proposed settlement, Lyft will admit to donating money to a candidate-controlled committee, but investigators are recommending a penalty of $50,000 – less than the maximum possible penalty – because the company did not know the committee was controlled by an elected official.

“At the time of the donation, Lyft carefully considered whether the proposed donation complied with all applicable laws and regulations, including ensuring that the PAC was not controlled by candidates prior to the donation,” a Lyft spokesperson told The Oaklandside. “These efforts included obtaining the PAC’s registration forms, which stated under oath that it was a non-candidate-controlled committee, and reviewing other materials that specifically stated that the PAC was not controlled by candidates.” Lyft did not respond when asked who requested the donation.

We contacted the individuals listed as officials in the committee’s official filings in 2020, including John Minot, Ernest Brown, Victor Flores, Matthew Lewis, Nicolas Nagle and Jonathan Bair. None of the individuals we contacted agreed to an official interview. None of them are named or accused of wrongdoing in the settlement.

Bair, who was special assistant to Libby Schaaf during her time as Oakland mayor, wrote in an email, “I was not involved in the settlement and have no comment.” In 2020, after Lyft made its contribution, Ernest Brown told The Oaklandside he did not know why the company had donated to the committee.

Why a ride-sharing company spent so much money to oust Kaplan

Lyft’s $100,000 donation in 2020 to oppose Kaplan and support her primary opponent in the race, Derreck Johnson, made headlines. At the time, it accounted for 90% of the total funds raised by the Committee for an Affordable East Bay, which was set up as an independent spending committee. State law allows such committees to raise and spend nearly unlimited amounts of money as long as they don’t partner with a candidate.

At the time of her post, Kaplan told The Oaklandside she believed Lyft wanted to oust her because she did not support the company’s demands to change its contract with the city to operate its bike-share and scooter-sharing franchise. She said Lyft successfully negotiated a similar deal in San Francisco that gave the company a monopoly position and “terrible prices.” In 2018, Kaplan also proposed imposing a tax on ride-sharing companies like Lyft and Uber. The companies lobbied Oakland authorities against the tax, but the city council rejected it.

When Johnson, a local businessman who founded the Home of Chicken and Waffles restaurant, entered the campaign against Kaplan four years ago, Schaaf supported him and made a maximum donation of $900 to his campaign committee, according to campaign finance documents.

Schaaf’s support of Kaplan’s opponent was no surprise to astute political observers. The mayor and the council member have had a frosty relationship. Schaaf defeated Kaplan in the 2014 mayoral election, and the two clashed when they served side by side in Oakland’s government.

Lyft’s contribution to the Committee for an Affordable East Bay helped pay for $35,000 in commercials and television spots attacking Kaplan and another $134,600 in spots praising Derreck Johnson, according to campaign finance filings.

Kaplan narrowly won re-election with 52% of the vote to Johnson’s 48%, after third-place candidate Nancy Sidebotham was eliminated in a ranked-choice election.

Two weeks after the election, Kaplan filed an ethics complaint against the Committee for an Affordable East Bay and another committee, accusing them of a series of election law violations. The Ethics Commission has not yet commented on the specifics of Kaplan’s complaint.