“They’re trying to purchase the entire political establishment … They’re trying to flood the whole apparatus.”
What can $43 million buy?
If you’re an alliance of rideshare giants and delivery app companies, it can buy millions of dollars in TV ads, high-powered consultants, and campaign workers who cross over with your biggest opponent.
Some say that money was meant to buy an election—and may still influence Massachusetts politics going forward.
Uber, Lyft, Instacart, and DoorDash poured the funds into a 2022 ballot initiative that would allow the rideshares to classify their workers as independent contractors, a status that has been hotly debated.
Attorney General Maura Healey filed a lawsuit against Uber and Lyft two years ago, saying the companies are misclassifying workers and illegally denying them employee benefits like overtime and paid sick leave and decrying the companies’ “unfair and exploitative practices.” As that lawsuit makes its way through the courts, nearly every observer is predicting that Healey, the Democratic nominee for governor, will easily win the election in November. Meanwhile, since the Mass Supreme Judicial Court earlier this year tossed a 2022 ballot question, rideshare companies—and the delivery operations that depend on them—have had a hard road ahead.
But those companies are not giving up. While the ballot question they financed is dead, they’re still pushing forward with plans to deny workers benefits available to other employees in the state. And campaign finance reports show how they’ve spent millions of dollars on national and state Democrats and progressive power players, trade groups, and consultants—with some of their hires also working for the Healey campaign.
That spending spree could still bear fruit by seeding the rideshares’ views through the state’s political infrastructure, according to Jeff Hauser, director of the policy watchdog group the Revolving Door Project.
“It normalizes some ideas because a large swath of people in the political chattering class start saying the same things about the topic,” Hauser said. “People inclined in the opposite direction might soften, undecided people might come over to that point of view.”
A self-described progressive Democrat may hold the corner office in 2023, but progressive and Democratic power players in Mass seem happy to take dollars to push rideshare agendas.
“They’re trying to purchase the entire political establishment,” said Wes McEnany, director of a coalition that opposed the rideshare ballot question. “They think that by doing that they can astroturf their campaign and erode our laws. They’re trying to flood the whole political apparatus.”
Ballots and bank statements
Along with the governor’s race, the 2022 ballot was set to contain a question with massive implications for workers in Massachusetts. The measure, pushed by Uber and Lyft, would say app-based drivers are independent contractors and not employees of those companies—and thus are unable to get benefits and protections from safety regulations available to employees, which is the crux of Healey’s lawsuit.
It was a similar proposal to the ballot measure Prop. 22, which passed in California in 2020, and which a state court later overturned (although rideshares are appealing). But in June of this year, the Supreme Judicial Court said the Mass question should not have been allowed on the ballot in the first place because of broad and vague language, and ordered it removed.
During the California campaign, rideshares and delivery companies spent more than $200 million in support of the ballot question. They didn’t reach that level in the Bay State, but still raised an eye-popping $43.6 million between the middle of 2021 and the SJC ruling—more than 10 times what Healey herself has raised in her gubernatorial campaign in 2022.
Healey raised $4.1 million in 2022 so far.
According to campaign finance reports, the pro-rideshare group Flexibility and Benefits for Massachusetts Drivers raised $17.8 million in 2021 and $25.8 million in 2022. Lyft gave $14.7 million and Uber $8.2 million, with both companies also “donating” support time and expenses. Rideshare-dependent companies also spent heavily—Doordash kicked in $3.7 million, while Instacart spent $17 million (including staff support time) on the campaign.
In comparison, the opposing campaign, MA Not For Sale, raised about $1 million through December 2021, mostly from unions, according to the most recently available reports. McEnany said the group ultimately raised about $2 million before the question was rejected by the SJC.
And because the question was tossed off the ballot, the rideshare companies wound up getting large amounts of their investment returned—Uber got $2.9 million of its donation back, while Lyft got $10.5 million and Instacart pulled back $10.9 million.
But that still left $14 million to be spent. And those expenditures show a heavy focus on organizations and consultants with significant ties to prior rideshare campaigns—along with the state and national Democratic party infrastructure.
“It’s not a certainty but in general a reason why money is spent is that it increases the odds of success,” Hauser said.
McEnany said rideshares and app-based companies are more than willing to spend large amounts of money up front if it means they can avoid paying higher wages or benefits later.
“If they’re able to preserve or change the law and rip off consumers and taxpayers,” McEnany said, “all of that is totally worth it.”
Payments and connections
The company that received the most money from the rideshare group, more than $5 million, was Pier 91 Media, an ad-buying company based in Washington, DC. According to a report from protocol.com, Pier 91 flies under the radar but “its mailing address is the same as a prominent Democratic-allied public relations company and political vendor known as GMMB, and local D.C. business records confirm that Pier 91 is a trade name of the latter firm.”
“GMMB boasts that it’s what “Presidents Joe Biden, Barack Obama and Bill Clinton have in common,” the Protocol article adds, and it can definitely brag about connections to the current president —a former vice president with the group, Patrick Bonsignore, was director of paid media for Biden’s 2020 campaign.
The campaign also gave $1.4 million to the Berkeley, California-based Trilogy Interactive LLC for advertising. According to its website, Trilogy bills itself as a “leading digital consulting firm focused on helping progressive political causes” and “the digital partner for labor unions”—who appear to be donating exclusively to the campaign opposing the one Trilogy was working for.
The campaign didn’t just spend on media buys. It also paid Leo Feler, a nationally-known economist who frequently makes media appearances and who advocated for Prop. 22, to create a report analyzing data around rideshare effects on the economy. The report, which said rideshare and delivery platforms generate $8.3 billion in economic activity in Massachusetts, was then touted on the campaign’s website. “My compensation in this matter is in no way contingent or based on the content of my opinions on this or any other matter,” Feler wrote in the introduction to the report, for which he was paid $116,000.
Bay State ties
Local political firms benefited from the rideshare campaign as well. Longtime political consulting firm the Dewey Square Group pulled in $2.6 million in consulting fees, and paid out another $4 million to subvendors, according to finance reports. Political operative Dan Cence’s firm Solomon McCown got $125,000 and when it merged into a new organization, Issues Management, that group got $50,000 as well. Prominent Boston law firm Foley Hoag—whose members include Healey’s predecessor, former Attorney General Martha Coakley—pulled in $467,000 from the rideshare group.
And digging into the list of vendors and subvendors—firms or people paid through larger organizations like the Dewey Square Group—shows a battalion of Bay State politicos with strong Democrat connections. TL Strategies, which is run by Tracey Lewis who managed Joe Kennedy III’s congressional campaign and worked on Elizabeth Warren’s 2020 presidential campaign before directing Joe Biden’s campaign in Georgia, pulled in $187,000. Another Warren campaign veteran, Annie Nagle, got nearly $100,000. Former Worcester Sheriff Guy Glodis raked in $100,000, with $50,000 under his own name and $50,000 through his consulting firm. Pilgrim Strategies, a consulting firm founded by former staffers of Congressman William Keating, hauled in $35,000.
The rideshares also hired numerous community activists and firms without political work in their history as consultants, but even they could have political connections. The management consulting firm of Conan Harris, the husband of Congresswoman Ayana Pressley, which focuses on improving diversity, was paid $113,000. Alex Tkachuk, whose Boston law firm received $15,000, is a lobbyist who has worked for Uber in DC. But she previously dealt with labor issues as counsel for the City of Boston under her old boss—former mayor and current Secretary of Labor Marty Walsh. And not all consultants had Democratic ties; South & Hill Strategies, run by former Gov. Charlie Baker spokesperson Lizzy Guyton, took in $46,0000.
“The Dewey Square Group specializes across the country, doing state and local work on behalf of national clients,” said Hauser from the Revolving Door Project. “They hire people to maintain really good relationships with community leaders and work with them on electoral campaigns, which binds them together in a more ideological way.”
“It’s hard for a corporation to maintain key relationships across the country, so they go to firms who specialize in hiring well-liked local people.”
While Healey has criticized rideshares, some of the companies have hired people with close ties to the attorney general. Beacon Research, which was co-founded by former Healey pollster Chris Anderson, was paid $148,000 for polling work by the rideshares. At the same time, Healey’s campaign also paid Beacon Research $182,000 for polling work.
Political operative Malaika Lucien received $45,000 from the rideshares throughout 2022, with her last pay date coming on July 29, according to campaign finance records. Two weeks later, Lucien announced she was becoming the Healey campaign’s deputy political director.
Steve McKenna was working for Healey at the same time he was taking money from the rideshares. Campaign finance records show McKenna getting nearly $40,000 from the Healey campaign in 2022, first as a consultant and then as a staffer—McKenna’s Twitter, where he stumps for Healey, says he’s a field director for the campaign. But finance records show him getting $50,000 for consulting for the rideshares as well from 2021 to June 2022, overlapping with the time he was consulting for the Healey campaign. McKenna used his Twitter account to plug the rideshares’ campaign as well.
A spokesperson said Healey’s campaign had no comment about the crossover. Hauser said he doubted those connections would influence Healey to reverse course on rideshares, but said the crossover would be beneficial to consultants looking to make future corporate ties. “If you have an organizing role for the Healey campaign, it gives you connections. You can market those connections for Uber or Coca-Cola or whatever company has a political ax to grind,” he said.
And the connections forged during this campaign can be valuable in the future. While the ballot question is currently off the table, there are other ways the law can change. A spokesman for Flexibility and Benefits for Massachusetts Drivers said the group had no comment about future plans or its past work, but the organization’s website said it “will continue to stand with drivers and fight to protect their flexibility and independence through the Massachusetts Coalition for Independent Work.”
In 2021, state lawmakers filed a bill that would also re-classify rideshare drivers as independent contractors. That bill died in committee, but McEnany said he expects another version in the next legislative session.
“I don’t think these companies are done,” he said. “We fully expect them to re-file a similar bill.”
Ed. Note: The original subtitle for this article was “How Rideshare and Delivery Companies Spent $43 Million Buying Influence In Mass.” We adjusted it for clarification.