The fight over gig work is ugly, expensive, and nowhere near over

No: “Massachusetts isn't for sale.” Gig companies: “Wanna bet?”

A car-shaped piñata

The fight for votes has become less about substance and more about a glut of cash — a bit like the tech industry itself, in 2022.

Illustration: Christopher T. Fong/Protocol

When Uber, Lyft, DoorDash and Instacart emerged victorious in their California campaign to continue classifying gig workers as independent contractors, they left behind a battlefield so flooded with cash that their opponents drowned in it. The most expensive ballot measure in California history cost the companies a little over $200 million; their opponents spent just $20 million.

Now, the gig companies have brought the Proposition 22 fight to Massachusetts. They are expected to once again break records for campaign spending, quite possibly surpassing the state record of $60 million spent across all ballot measures in 2020. Lyft already broke the state’s one-time political contribution record when it made a $14.4 million donation late last year.

The “No” campaign — led by labor groups — admits its defeat in California was crushing. But its new leader, Wesley McEnany, thinks he has a novel strategy that could actually prevent the same type of bloodbath.

For McEnany, fresh from two years helping to lead the campaign to unionize tech workers at the Communication Workers of America, there’s no question that the ballot measure in California, and the similar one now proposed in Massachusetts, are deeply unfair to the companies’ workers. But he also believes that if the campaign keeps the fight solely about the workers themselves, they could lose again.

So instead, the campaign has rebranded itself from the “Coalition to Protect Workers Rights” to “Mass Not For Sale.” For the next eight months, McEnany and the “No” coalition will argue to the commonwealth of Massachusetts that “Big Tech” is trying to buy a law, and that voters should be outraged. “Big Tech” is a popular public enemy these days, so the “No” coalition plans to take advantage of that trope and bring up issues like privacy, safety and antitrust.

“Here we have corporations that are willing to spend hundreds of millions of dollars to use a ballot measure process to buy a law,” he said. “We are talking about workers — workers are going to be a very centered strategy, and drivers are part of the strategy. But if we allow the conversation to strictly be about one thing, the amount of resources and money [these companies] have to sort of confuse that issue is undeniable.”

The “Yes” campaign, represented by a group called the Massachusetts Coalition for Independent Work, is so confident in its legislative strategy that its spokesperson, Conor Yunits, told Protocol he was almost certain the Massachusetts legislature would create a law enshrining protections for gig-work companies before the ballot question ever reaches the ballot box. But in case the legislature does not, the campaign already has more than $17 million in the bank — and the opposition expects that to swell to $100 million by November. (Protocol contacted Uber and Lyft for this story. Uber did not respond and Lyft directed us to Yunits).

The fight for votes has become less about substance and more about a glut of cash — a bit like the tech industry itself, in 2022.

Despite the financial shenanigans, this fight has enormous implications for the future of work. Millions of full-time American jobs that currently provide health insurance and sick leave are primed to be giggified. This giggification is already spilling over into other sectors, such as health care: In California, a new Prop-22 simulacrum has emerged that proposes to classify health care workers who find their jobs on digital platforms as independent contractors, much like ride-hail and delivery drivers. And if the gig companies succeed in the deep blue, labor-friendly Massachusetts, they’ll have a political playbook ready to export around the U.S.

A three-pronged approach

The gig companies are fighting their case in courts, in the Massachusetts legislature and potentially on November ballots. This three-pronged approach is part of what makes this campaign so complicated and expensive. It also shows the gig companies have adopted a more sophisticated approach since the California Prop. 22 campaign — in Massachusetts, the coalition has a plan, a backup plan and a backup-backup plan.

The first prong — the court battle — kicked off in July 2020, when Massachusetts Attorney General Maura Healey (now the Democratic front-runner in the state’s gubernatorial election) filed a lawsuit arguing Uber and Lyft drivers should be classified as employees under existing state law.

Healey asserted that Massachusetts Wage and Hour Laws required gig companies to reclassify workers as employees. These laws had been in place for years, but hadn’t been enforced for gig companies. Healey’s lawsuit sought to grant gig workers access to minimum wage guarantees, earned sick time and overtime. (At the start of the pandemic, Uber and Lyft gave drivers limited assistance in the form of stipends for those who tested positive for COVID; drivers struggling to make ends meet later became one of the largest cohorts to receive federal aid under the Economic Injury Disaster Loans program.)

In March 2021, Uber and Lyft lost a motion to dismiss the lawsuit. While the suit is still ongoing, the gig companies don’t need to win if they are successful in changing the law underpinning it, either through the legislature or the voter ballot measure.

The gig companies decided to push for the ballot question because of the lawsuit, Yunits told Protocol. And in September, Healey certified two ballot questions put forth by the gig coalition — one that would require additional safety training for drivers, and another that wouldn’t. Voters will likely see only one version of the question on ballots, if it gets to that point.

But the gig coalition doesn’t actually need the question to make it onto the ballot, and it would save them a lot of trouble if it didn’t. Under Massachusetts law, the state legislature can choose to pick up ballot initiatives and decide the outcome for themselves, cutting in front of voters.

The Legislature now has the option of passing the measure directly, proposing a substitute or doing nothing. If they fail to do anything before May, the gig coalition will have until July to collect an additional 13,374 signatures. Only then would the question appear on ballots.

“We continue to push for a legislative solution to this issue and we’re confident that our legislative leaders can get it done,” Yunits said.

Protocol pressed Yunits on this further, asking whether he thought a legislative solution was more likely than the measure going to the ballots. “We remain very confident,” he responded.

The legislative opposition doesn’t share this view. “We anticipate that this will go before the voters this November,” said Massachusetts State Senator Paul R. Feeney. “We're going to be doing everything that we can to make sure that our voters understand the full truth of what companies like Uber and Lyft and DoorDash are trying to do here.”

Within the Statehouse, Feeney senses that the gig companies are preparing for the measure to go to ballots in November, despite their statements to the contrary. “There doesn’t seem to be much engagement in trying to figure out a legislative solution to this,” Feeney said. “We saw in California where they spent an ungodly amount of money to try and buy a law and confuse voters, and I think that’s where we’re heading in Massachusetts.”

In January, the No Campaign also filed a complaint against the ballot measure in Massachusetts Supreme Judicial Court, arguing that it shouldn’t have been certified in the first place.

“Not only do these proposals eliminate otherwise mandated rights, but they also blatantly violate our Constitution,” explained Nicole Decter, General Counsel of the Coalition to Protect Workers’ Rights.

The complaint also alleges that the measure is misleading to voters. It claims that Healey’s petition summary doesn’t adequately explain that drivers should already be classified as employees under Massachusetts state law.

It’s likely that neither campaign will get its best-case scenario: The “Yes” campaign won’t get a legislative victory to bypass ballots, and the “No” campaign won’t block the ballot initiative altogether through its court filing. That means Massachusetts voters will likely get the final say. If that happens, even more money would come flooding into Massachusetts; the debate would leave the cloistered rooms of the Statehouse and enter the frames of millions of smartphones and television screens.

Information warfare

“You hear the same lie four times, it becomes truth.”

That’s what Nicole Moore took away from the California Prop. 22 campaign. Moore is a part-time Lyft driver and organizer for Ride Share Drivers United. From her perspective, California voters were so inundated by the Yes Campaign’s media messaging that they didn’t fully understand what they were voting for.

Exit polls from California showed that 40% of those voting “yes” on Prop. 22 believed they were helping ensure that Uber, Lyft and DoorDash employees could earn a livable wage. But according to a 2019 UC Berkeley study, California gig workers would only really make $5.64 an hour, after accounting for hidden costs such as unpaid wait time and payroll taxes from the “guaranteed” minimum wage of $15.60. (Uber disputed the results, arguing in part that drivers should not be considered “on the clock” when waiting for ride assignments since they retain the agency to accept or reject offers.)

Moore said the gig companies saturated the media market to such an extent that “within a few hours, in your commute home, you’ve heard a couple messages on the radio, you open your Facebook when you get home [and] you get a message or two there, and you turn on the evening news and you get another message.”

The media campaign also directly targeted drivers, who received messaging from Uber and Lyft. The companies warned they would leave California entirely if the measure didn’t pass.

Lyft has once again started claiming that drivers are on its side. “Massachusetts drivers overwhelmingly support the ballot measure by a 7:1 margin because it allows them to keep their independence,” Lyft co-founder John Zimmer said in a November 2021 earnings call.

This kind of media saturation requires wads of cash. By November, the “No” campaign anticipates their opponents will have raised at least $100 million. The target fundraising goal for their own campaign is somewhere around $10 million, of which they’ve already raised about $1 million from a mix of labor and union groups. McEnany said he expects the financial difference to be slightly less important here than it was in California, given that the two groups have only a few major media markets to flood with ads, rather than California’s 14 — four of which are the most notoriously expensive in the country.

Beth Enrique Griffith, one of the members of the “No” coalition’s board, also believes that the money will matter less because the coalition is planning an early grassroots campaign with organizing groups across Massachusetts, a strategy largely absent from the California fight. “We’re going to hit the ground running, starting sooner rather than later, in this campaign,” she said. “We immediately connected with our grassroots organizations around the commonwealth and implemented a strategy and got them involved.”

The “Yes” campaign anticipates that each company will contribute about equally to the fundraising pool eventually, meaning that Uber, DoorDash and Instacart will likely match the record-breaking $14.4 million from Lyft at the very least, if they haven’t already (the campaigns aren’t required to report their donations since 2021 until September of this year). By the end of 2021, the “Yes” coalition had already spent more than $1.7 million just to gather signatures for the ballot proposal, another $600,000 on consulting and more than $100,000 on polling.

Those in-house polls show the ballot measure in a very favorable light. They ask gig workers whether they want to be independent contractors or employees (64% are in favor of being contractors), whether flexibility or full-time employee benefits are more important to them (70% say flexibility) and whether they support or oppose the ballot measure (83% support).

The opposition believes those questions are misleading and ask voters and drivers to believe a false paradigm: The gig companies want people to believe it’s flexibility or benefits, while the opposition thinks it’s possible to have both. But the “No” campaign also doesn’t think it can win when it’s arguing only about those details — instead, they believe they need to convince voters that Uber, Lyft, DoorDash and Instacart are trying to buy a piece of legislation.

Because for the opposition, it’s not only about Massachusetts, but the American way of life: What remains of today’s middle class will become tomorrow’s food couriers, on-demand nurses and uninsured ecommerce warehouse workers.

“We know that if they are successful here in Massachusetts with drivers, that this is only the beginning,” Feeney said. “We’re on the vanguard right now of protecting workers from this tidal wave of gig economy models that will carve out a separate class of workers.”

Massachusetts is set to become a proving ground for future Prop. 22-esque pushes. Opponents of the ballot measure believe Massachusetts will prove to be a tougher test than California for the gig companies, seeing as the commonwealth has a long pro-labor history and a highly engaged voter base. If the companies that depend on gig-worker labor can win in Massachusetts, they’ll be ready to win just about anywhere else.

“Our proposal for a new pragmatic approach is supported by 82% of drivers and 76% of voters,” Uber CEO Dara Khosrowshahi said in a November 2020 earnings call, referencing the passing of Prop. 22 in California. “It's a priority for us to work with governments across the U.S. and the world to make this a reality.”


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