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...
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