October 25, 2021
William Gross, the former Boston police commissioner backing Annissa Essaibi George’s mayoral campaign with an endorsement and his own super PAC, took to television in the days leading up to the September preliminary.
Looking at the camera and wearing a light hat and a dark suit, a smiling Gross said, "On Tuesday, September 14, I'm voting for Annissa Essaibi George for mayor of Boston."
But elections department records show Gross did not vote in the preliminary. The Reporter reviewed the city’s voter file, which is a public document.
George Regan, the founder of Regan Communications Group who has been working with the super PAC, confirmed that Gross didn’t vote on Sept. 14. In an emailed statement, Regan said Gross went to a polling station in Roslindale that day to vote for Essaibi George. He showed his driver’s license and he was told he could not vote because the Registry of Motor Vehicles had made a change in his address, according to Regan.
“Commissioner Gross appealed the mistake on the spot and he's received a letter from the City stating that the mistake has been corrected and he will be voting for Annissa Essaibi George for Mayor of Boston,” Regan said in the statement.
The general election is set for Tuesday, Nov. 2.
Gross, who has previously listed a Milton address, is now registered in the city of Boston, and he listed his party affiliation as unenrolled, according to the elections department.
Gross endorsed Essaibi George in May. A Baltimore native who was raised in Dorchester, Gross considered a mayoral run himself before abruptly retiring as police commissioner earlier this year. He was first appointed by former Mayor Marty Walsh in 2018, becoming the city’s first Black police chief.
At the end of August, Gross filed paperwork forming a super PAC called “Real Progress Boston” and listed a Roslindale address. Super PACs can raise and spend unlimited amounts of money, but they cannot coordinate with candidates. In Massachusetts, the outside groups typically draw their funding from unions and wealthy donors.
In the closing days of the five-way mayoral preliminary, New Balance chairman Jim Davis, a top GOP donor, joined police unions in pouring money into “Real Progress Boston,” which spent more than $550,000 on television, radio and newspaper advertisements, which featured Gross touting Essaibi George’s candidacy.
Essaibi George has called on outside groups to stay out of the race, while mayoral rival Michelle Wu has asked them to stay positive. The Essaibi George outside groups — the other super PAC, “Bostonians for Real Progress,” is operating separately from “Real Progress Boston” — have ignored the requests, with radio and TV ads taking aim at Wu’s plans for police funding.
Wu’s super PACs, much of their funds coming from attorneys and environmental groups, have focused on promoting the Roslindale city councillor at-large.