Oakland At-Large Councilmember Rebecca Kaplan wore two pins during a virtual press conference on Monday: One for her re-election campaign and another in opposition to Proposition 22, the statewide ballot measure funded by gig companies, such as Lyft, Uber, and DoorDash.

In both campaigns, mega-tech companies are spending astronomical amounts of money to affect the outcome. An Independent Expenditure Committee (IE) funded with a $100,000 contribution from Lyft, aims to defeat the incumbent Kaplan, a long-time opponent of the unfettered expansion of car-sharing companies in Oakland.

The push by ride-hailing companies to pass Proposition 22, the statewide measures that progressives across the state fear will exempt companies like Lyft and Uber from a number of labor laws, has flooded the airwaves and mailboxes over the past month.

Overall, $183 million is likely to be spent in support of Proposition 22, making it the most expensive ballot measure campaign in state history.

Californians for Independent Work, an IE backed by Lyft contributed $100,000 on Sept. 21 to an Oakland IE that backs Kaplan’s council opponent, named the “Committee for an Affordable East Bay supporting Derreck Johnson and opposing Rebecca Kaplan for Oakland City Council At-Large 2020, Sponsored by Lyft, Inc.” By law, IEs are prohibited from coordinating their efforts with campaigns they support or oppose.

“We are facing unprecedented oppositional expenditures from billionaires who are trying to buy our democracy,” Kaplan said during a Zoom call that also functioned as a fundraising pitch. “In Oakland, they’re trying to buy a council seat.”

Southern California Assemblymember Lorena Sanchez said the enormous amount of spending in support of Proposition 22 is leaking out to smaller races across the state, including Kaplan’s bid for re-election against Oakland restaurteur Derreck Johnson. Perennial council candidate Nancy Sidebotham is the third candidate in the race.

“And while they’re at it they try to throw a little money here and there to defeat candidates who stand up for values, who stand up to these billion dollar corporations,” Gonzalez said.

The IE against Kaplan’s re-election is a clear threat from billionaires, said Ash Kalra, an assemblymember who represents the South Bay.

“This is a warning to every elected official out there at every level of government. If you come after these billionaires, they’re going to come after you and we cannot let that stand,” Kalra said.

At first glance, Kaplan’s re-election did not seem in danger. She remains popular in Oakland and has a level of name-recognition topped only by Mayor Libby Schaaf. But the emergence of Johnson, and a clear fundraising advantage over Kaplan, in addition, to the help from the Lyft-funded IE, has put the incumbent on the offensive.

Kaplan has raised a populist banner in recent weeks, including on Monday’s Zoom call, when she blasted Lyft for spending heavily to achieve special favors, tax loopholes and monopolies in Oakland. “They want the right to abuse communities and workers,” Kaplan said. “When I wouldn’t go along with that, they decided to put more money than we’ve found any record of any company ever putting into a local council race to try to oust me, because I’m standing up for the people of Oakland.”

Later in the call, Kaplan told Lyft to “put their money where there mouth is,” and challenged the company to a debate.