Gross would face hurdles, opportunity in mayoral run

Boston police commissioner weighing campaign at time of tough questions for law enforcement 

IF WILLIAM GROSS jumps into the race for mayor of Boston, one thing is clear: He’ll do so at a time when issues he oversees as the city’s top police official are receiving tremendous attention and scrutiny. Whether that would play more to his benefit or detriment is the big question he may be weighing. 

Reports over the weekend said Gross, who became the city’s first black police commissioner in 2018, was seriously considering a mayoral run following Mayor Marty Walsh’s selection by President-elect Joe Biden to serve as labor secretary. On Monday, Gross said he is giving a run “deep consideration.”

An entry by Gross would shake up the still-forming race to succeed Walsh, who had been widely expected to seek a third term this fall. “He would be an instantly credible candidate for mayor,” said former Boston city councilor Tom Keane. 

But a Gross campaign would come amid a harsh national spotlight on police killings of unarmed black civilians and on the heels of months of debate at the city and state level that have ushered in reforms to the Boston Police Department and to the oversight of departments across Massachusetts. 

More than 4,000 people have quickly signed up for a Facebook group promoting a Gross mayoral run. But whether the political environment is right for a police official to run to lead a major US city would become a central question for a Gross campaign.

“I think Gross should read the room,” said Monica Cannon-Grant, a longtime activist in Boston’s black community and the founder of the nonprofit service organization Violence in Boston. “The climate right now in this country does not believe that a cop that says ‘blue lives matter’ should be in an elected position as we’re watching people die in this country at the hands of police officers.” 

Cannon-Grant led the largest protest in Boston over summer following the policing killing of George Floyd in Minneapolis, part of a wave of demonstrations across the country decrying police brutality against black Americans. She said it is the wrong time to even consider installing a top police official in the mayor’s office.

Rev. Jeffrey Brown, a leader of the clergy-led 10 Point Coalition that formed in the 1990s and worked with police to quell gang violence, was more circumspect but issued a caution. 

“He is a wonderful public servant and he’s a cop’s cop,” Brown said of Gross, who became a Boston police officer in 1985. “But the business of being the mayor of the city requires that you do more, and I don’t know how that plays in all the communities to have the police commissioner, in this time when we are trying to do police reform, become the mayor of the city.” 

Gross has fully embraced the reforms proposed last year by a city-appointed task force that Brown was a member of, including creation of a new oversight board, with subpoena power, to investigate allegations of police misconduct. Gross, who arrived in Boston from Maryland with his mother when he was 12 and grew up in Dorchester, touts himself as a reformer and a community-oriented leader who came of age in and understands the communities most affected by crime and policing. 

But he has clashed several times with reform advocates and elected officials in the two and a half years since he was appointed commissioner. Only months into his new role, he lashed out at the ACLU in a Facebook post, calling the group “paper warriors” always ready to take the police department to court, while its officers bravely risk their lives to keep residents safe. 

Minority elected officials criticized Gross for his post, while the president of the Boston Police Patrolmen’s Association, the city’s largest police union, said officers were thrilled with the statement. 

Last June, Gross faced heat for meeting in Boston with Attorney General William Barr on the heels of the tear-gassing of peaceful demonstrators in Washington’s Lafayette Park to enable President Trump’s controversial walk from the White House to a nearby church for a photo-op holding a Bible. 

“Defund whatever the hell this is,” City Councilor Andrea Campbell tweeted in reaction to a photo posted by the attorney general’s office of a grinning Barr and Gross. Campbell is now one of two declared candidates for mayor, along with City Councilor Michelle Wu.

In June, Boston Police Commissioner William Gross took flak after meeting with and posing for a picture with then-Attorney General William Barr.

Jim Jordan, a policing consultant who served as director of strategic planning for the Boston Police Department in the early 1990s, said police chiefs across the country are feeling embattled, and residents of many cities “would be aghast” at a run for mayor by their top police official.

With lots of sentiment that Boston may embrace the opportunity to elect its first mayor of color, however, Gross could be uniquely positioned to satisfy that call while appealing to more moderate or conservative voters.

City Councilor Michael Flaherty deflected questions from the Boston Globe on Sunday about whether he might enter the race. But the veteran white at-large councilor from South Boston told the paper, “People are calling me across the city saying ‘If you’re not running, I’m with Willie Gross.’”

“He’s looking for support from conservative whites and police,” Cannon-Grant said of a potential Gross campaign. “The black community is not having it. Not when we’re constantly on the receiving end of FOIs and being racially profiled,” she said, invoking the acronym for “field interrogation and observation” stops by police. 

But Gross could have broader appeal than just that, including among some minority voters. He would certainly have high name recognition. 

“The police executive is the second most well known figure in any municipality,” said Jordan.

But as he pointed out, the high profile role of police commissioner has not always translated into electoral success. Jordan worked for Francis “Mickey” Roache, a Boston police commissioner in the 1980s and early 1990s who flopped as a candidate for mayor in 1993. 

Keane said Gross could find an opening with a large swath of Boston voters that have long gravitated toward more moderate leaders.  

Meet the Author

Michael Jonas

Executive Editor, CommonWealth

About Michael Jonas

Michael Jonas has worked in journalism in Massachusetts since the early 1980s. Before joining the CommonWealth staff in early 2001, he was a contributing writer for the magazine for two years. His cover story in CommonWealth's Fall 1999 issue on Boston youth outreach workers was selected for a PASS (Prevention for a Safer Society) Award from the National Council on Crime and Delinquency.

Michael got his start in journalism at the Dorchester Community News, a community newspaper serving Boston's largest neighborhood, where he covered a range of urban issues. Since the late 1980s, he has been a regular contributor to the Boston Globe. For 15 years he wrote a weekly column on local politics for the Boston Sunday Globe's City Weekly section.

Michael has also worked in broadcast journalism. In 1989, he was a co-producer for "The AIDS Quarterly," a national PBS series produced by WGBH-TV in Boston, and in the early 1990s, he worked as a producer for "Our Times," a weekly magazine program on WHDH-TV (Ch. 7) in Boston.

Michael lives in Dorchester with his wife and their two daughters.

About Michael Jonas

Michael Jonas has worked in journalism in Massachusetts since the early 1980s. Before joining the CommonWealth staff in early 2001, he was a contributing writer for the magazine for two years. His cover story in CommonWealth's Fall 1999 issue on Boston youth outreach workers was selected for a PASS (Prevention for a Safer Society) Award from the National Council on Crime and Delinquency.

Michael got his start in journalism at the Dorchester Community News, a community newspaper serving Boston's largest neighborhood, where he covered a range of urban issues. Since the late 1980s, he has been a regular contributor to the Boston Globe. For 15 years he wrote a weekly column on local politics for the Boston Sunday Globe's City Weekly section.

Michael has also worked in broadcast journalism. In 1989, he was a co-producer for "The AIDS Quarterly," a national PBS series produced by WGBH-TV in Boston, and in the early 1990s, he worked as a producer for "Our Times," a weekly magazine program on WHDH-TV (Ch. 7) in Boston.

Michael lives in Dorchester with his wife and their two daughters.

“I do not think the next mayor of Boston is going to be a white male, but I do think there’s going to be a struggle over does Boston swing far left or does it still favor middle-of-the-road governance. Menino pioneered middle-of-the-road governance,” he said of the late former mayor. “And Marty Walsh kind of followed that.” 

Of course, Gross’s positions on a whole range of issues are unknown. “We don’t know what he believes,” said Keane. “But I’m pretty sure it won’t be ‘defund police.’”