Two years ago, Massachusetts braced itself for what was expected to be the most expensive ballot measure campaign in the state’s history. That question, brought by ride-hailing companies to classify their gig workers as independent contractors, was kicked off the ballot by a ruling from the state’s highest court.
In just a few weeks, the state should know if the fight and the ad dollars will be back on the horizon. And this time, there could be ballot measures on both sides.
At the heart of the new dueling ballot measures, years of legislative efforts, and an ongoing lawsuit is a seemingly straightforward question: Are ride-hailing workers, who conduct pick-up and drop-off services through app-based platforms, more akin to ordinary employees under state law or more like independent contractors and therefore not guaranteed the benefits and protections of standard employment law?
This question could be resolved in a few ways, all on long timelines. A ride-share backed coalition and the state’s largest service workers union have submitted propositions for the 2024 ballot, awaiting certification from the attorney general’s office by September 6.
The Massachusetts Coalition for Independent Work – financed by Uber, Lyft, Instacart, and DoorDash – is taking multiple runs at the question, submitting nine versions of the “law establishing that app-based drivers are not employees” measure.
Last year, the Supreme Judicial Court tossed an earlier ballot measure trying to establish independent contractor status for app-based drivers. The court concluded that the question was impermissibly trying to do too many unrelated things – not only setting out certain benefits for ride-share workers in exchange for independent contractor status, but also including language related to accident liability and contract formation.
In giving the attorney general’s office an array of ballot measure options, all including the independent contractor language and certain guaranteed benefits, the coalition is hedging its bets and hoping that some version of the question clears the legal bar to appear on the ballot and survive the courts. “We want voters to be able to decide this issue,” said Conor Yunits, a spokesman for the coalition.
It may well be up against a ballot measure backed by the service workers union, submitted by Roxana Rivera, who leads SEIU 32BJ in Massachusetts. Her petition “giving transportation network drivers the option to form a union and bargain collectively” would do just that. Union advocates say the gig economy is structured to give the companies immense power over the individual drivers, and codifying a right to collective bargaining would give the drivers more standing to negotiate for better work conditions and pay.
Rivera’s petition language is pulled from one of several ongoing legislative efforts. But neither the ride-share coalition nor the union groups are waiting to see if bills mirroring the ballot language die on Beacon Hill.
“The commonwealth of Massachusetts recognizes that technological advancement has generated new “digital marketplaces” in the transportation sector, in which companies connect, through electronic media, customers seeking passenger transportation services to persons willing to supply that transportation service,” the Rivera ballot initiative and a current bill proposed by Sen. Jason Lewis read. “These persons often suffer poor pay, inadequate health coverage, and irregular or inadequate working hours.”
Rideshare drivers themselves are split on the question, proponents of the independent contractors classification argue. Many value their scheduling flexibility and fear a worker classification would inhibit their ability to work for multiple apps at once to supplement other income, the group says.
The Commonwealth is set up for a busy 2024 on the matter. The attorney general’s office is still pursuing a lawsuit against Uber and Lyft, started by then-Attorney General Maura Healey. Healey, and her successor Andrea Campbell, argued that these companies were deliberately and incorrectly classifying their drivers as independent contractors.
It looks like a trial is on the books, though a ways off. The next hearing is scheduled for April 2024, with a trial slated for that May.
One certainty looms – if the attorney general’s office okays an app-based worker ballot measure, the battle will be pricey. A California ballot campaign backed by similar coalitions that successfully classified ride-share gig workers there as independent contractors cost over $200 million, the most expensive ballot measure ever launched in the United States.
JENNIFER SMITH
FROM COMMONWEALTH
Online Lottery after all? Although lawmakers opted against including a House plan to authorize online lottery ticket sales in the final 2024 budget, in late July a New York-based company called Jackpocket made Massachusetts the 17th state where residents can order lottery tickets on their phone or desktop computer and have someone go pick them at a retail lottery outlet. Two years ago, the then-director of the state lottery suggested companies offering such services were “operating outside the law,” but no action has been taken to regulate or rein in Jackpocket since it began operating here. Read more.
OPINION
State child welfare system ‘abysmal’: Retired Worcester County Juvenile Court judge Carol Erskine says the state’s child welfare system is in shambles, and nothing seems to change after repeated tragedies, which she says only result in investigations, apologies, and promises of reform, before the whole cycle repeats itself with the next horrible episode. Read more.
FROM AROUND THE WEB
BEACON HILL
The state broke ground on a new $482 million veterans home in Holyoke to replace the existing facility where more than 70 veterans died of COVID during the peak of the pandemic amid chaotic mismanagement and allegations of neglect. (Boston Herald)
Anne Gobi, the state’s new rural affairs director, tells MassLive she hopes to be a “strong voice” for Massachusetts towns.
MUNICIPAL MATTERS
An attorney for the Boston City Council filed an internal complaint claiming she felt “intimidated, ridiculed, harassed and bullied” by three councilors – Ricardo Arroyo, Kendra Lara, and Julia Mejia – during tense redistricting proceedings in April. Arroyo and Lara both say the conflict was with Council President Ed Flynn, not the staff attorney. (Boston Herald)
HEALTH/HEALTH CARE
The Valley Springs Behavioral Health Hospital is expected to open in October, with the 150-bed Holyoke facility providing behavioral health care for children, adolescents and adults. (Daily Hampshire Gazette)
WASHINGTON/NATIONAL/INTERNATIONAL
Former president Donald Trump and 18 others were indicted in a sweeping indictment by a grand jury in Georgia that alleges a broad conspiracy to overturn Joe Biden’s victory in the state in the 2020 presidential election. It is the fourth indictment Trump has faced this year, but the first in state court, where he would have no power to halt proceedings or issue pardons to himself or others if elected president next year. (Washington Post)
ELECTIONS
Democratic presidential candidate Robert Kennedy Jr. says he would support a federal abortion ban after three months of pregnancy, but his campaign later claimed he misunderstood the question because it was asked in a noisy exhibit hall at the Iowa State Fair and said he “does not support legislation banning abortion.” (Boston Herald)
Brockton businessman Hamilton Rodrigues, who is running for mayor, is facing questions about his residency. (The Enterprise of Brockton)
BUSINESS/ECONOMY
Home prices in Greater Boston continue their upward march. (Boston Globe)
TRANSPORTATION
State officials say they’ll try to get federal funding to replace one of the Cape Cod bridges at time, rather than both of them, with their initial efforts focused on the Sagamore Bridge. (Boston Globe)
CRIMINAL JUSTICE/COURTS
The state’s police oversight board, the Peace Officer Standards and Training Commission, will soon release records of more than 4,000 employer-substantiated complaints against officers. (MassLive)

