Lyft makes largest one-time political donation in Massachusetts history, fueling gig worker ballot fight

A Lyft light sat on the dashboard of a vehicle in this file photo from New York.Jeenah Moon/Bloomberg

The coalition pushing petitions that could reshape how gig economy workers are classified in Massachusetts took in the single largest political donation in state history last month, helping fund a phalanx of consultants, pollsters, and signature gatherers driving the questions toward the ballot.

The rideshare giant Lyft gave a whopping $14.4 million to a committee supporting the petitions, most of which came in a $13 million donation on Dec. 30, newly released records show. The single contribution is the highest the state Office of Campaign and Political Finance has ever listed in an online database that tracks reported donations to campaigns, ballot question coalitions, or other political committees regulated under state law.

It made up the bulk of the $17.8 million in donations and in-kind contributions the tech-backed ballot question committee reported taking since its launch in early August.

The vast sums underscore what was long expected: The debate over whether rideshare drivers, DoorDash delivery people, and others should be classified as independent contractors or employees is drawing millions of dollars from the same companies that prevailed with voters in a costly ballot fight in California in 2020.

The money here has helped pay for some of Massachusetts best-known political consultants. On the committee’s payroll are the Dewey Square Group, a public affairs firm with deep roots in Democratic politics, and Solomon McCown & Cence, a public relations outfit well versed in ballot question fights.

The committee also enlisted Conan Harris & Associates, a management consulting firm run and founded by the husband of Representative Ayanna Pressley. Harris’s work appears to put him at direct odds with Pressley’s own stance on the issue. The second-term Boston Democrat has backed calls to treat gig workers as employees, arguing last year that they are being “misclassified” as contractors.

“All of the coalition members have committed to providing significant resources to achieve our shared goal,” said Conor Yunits, a spokesman for the committee known as Flexibility and Benefits for Massachusetts Drivers. “This is just the beginning of our effort.”

California’s $201 million measure, known as Proposition 22, was the most expensive in the state’s history, with labor officials on one side and ride-hailing and delivery companies on the other. Uber, Lyft, and DoorDash contributed a combined $160 million to that campaign.

That state’s voters overwhelmingly sided with the tech companies, allowing them to continue treating drivers as independent contractors. But the matter has also been embroiled in court disputes, with a California judge declaring it unconstitutional in August.

That battle is now brewing in Massachusetts where, absent action by the state Legislature, it is likely to be decided by voters in November.

The question of how thousands of workers should be treated legally has major implications for the rights and benefits they are entitled to in the state, as well as for some of the country’s most well-known gig economy companies.

If backed by voters, the tech industry-backed ballot petitions would allow Uber, Lyft, Instacart, and DoorDash to continue classifying their drivers and deliverers as independent contractors — instead of as employees — while also granting the workers some new benefits.

Supporters say the proposal would give workers the flexibility they cherish, while also granting them new benefits including health care stipends and paid sick time. Labor advocates, however, say the gig workers already should be guaranteed the rights and benefits of full employees under state law, and argue that in practice, few workers actually would receive the new benefits promised in the proposal.

The tech-backed committee is pushing two slightly different versions of the question, one of which would require paid safety training sessions for drivers, including topics like collision avoidance and sexual assault prevention.

Proponents are expected to move forward with only one question, the secretary of state’s office said last month after the measures gathered more than the 80,239 signatures required to move toward voters’ hands.

The ballot petitions now sit with the Legislature. If Massachusetts lawmakers do not take any action on them, proponents must file an additional 13,374 signatures by July 6 to secure a place on the ballot.

But gig economy companies are hardly waiting. Lyft’s record-setting donation flowed in just days after the committee cleared the initial signature-gathering hurdle, adding to donations from Instacart, which contributed $1.2 million; DoorDash, which put up $1.17 million; and Uber, which contributed a little more than $1 million.

Among those aiding the campaign is Harris, a former City of Boston staffer who started his own firm days before his wife was sworn into office in 2019. The committee has paid his firm roughly $43,300 since September for what Yunits described as “grass-tops outreach” to community leaders, business groups, churches, and others about the ballot measures.

Pressley has indicated she disagrees with their position. She backed Labor Secretary Martin J. Walsh last spring after the former Boston mayor said that a lot of gig workers should be classified as employees.

“Gig economy workers should not be able to be misclassified as contractors,” Pressley wrote on Twitter in May, thanking Walsh for his comments. “They need benefits and full labor protections.”

A Pressley aide said her stance has not changed. “The Congresswoman has consistently said that gig economy workers should be classified as employees, and should have the rights and protections that employees have,” said Harry Shipps, a Pressley spokesman.

Harris did not immediately respond to a request for comment Tuesday.

Solomon McCown & Cence and the Dewey Square Group were also involved in the unsuccessful effort to beat back a ballot question last year that expanded the state’s “Right to Repair” law, itself a $50.7 million campaign that stands as the most expensive in Massachusetts history.

The firms also helped the successful push against a 2018 ballot that would have set strict limits on the numbers of patients assigned to hospital nurses. The Massachusetts Health and Hospital Association, the powerful trade group that represents hospitals’ interests on Beacon Hill, set a record in that race by funneling $24.6 million toward defeating the ballot question, the most ever contributed by a single entity.

Separate from the ballot petitions, Attorney General Maura Healey is suing Uber and Lyft over the same issue. Her office argued that the tech giants are currently breaking the law by failing to classify drivers as employees.

The labor-backed committee opposing the questions, known as the Coalition to Protect Workers’ Rights, has yet to file a report detailing its contributions and spending for the entire year.

But its leaders seized on the opponents’ filing, framing it as an attempt to “buy a giant loophole” in state law.

“Massachusetts is not for sale,” said Steve Tolman, president of the Massachusetts AFL–CIO, one of the labor groups opposing the measures. The labor-backed committee reported raising $464,500 within two months earlier last year, but Tolman said it would be a challenge for opponents of the ballot measures to match its supporters’ donations.

“From a dollar value, I imagine that will be very difficult,” he said.