Rollins brings mandate for change – and blunt style – to Suffolk DA’s job

With reform talk in the air, Boston’s new prosecutor prepares to take the reins

RACHAEL ROLLINS DEFIED expectations when she rolled to a decisive victory this fall in the race for Suffolk County district attorney. She won a five-way Democratic primary, outpacing a field that included the favorite of the law enforcement establishment, and went on to trounce an independent candidate in the November general election. The seat was open for the first time in 16 years after longtime DA Dan Conley opted not to seek another term. For Rollins, a 47-year-old single mother who had just completed treatment for breast cancer, it was a grueling nine-month marathon of debates, door-knocking, fundraising, and phone banks.

And now comes the hard part.

Rollins rode a national wave of rethinking criminal justice policy that has seen reform-minded DAs elected in several major cities and a sweeping crime bill passed on Beacon Hill. She has pledged to end the “criminalization” of poverty, mental illness, and addiction – social factors that Rollins says often lie behind criminal activity and are better addressed through services and treatment than jail. Now she has to translate those heady aspirations into day-to-day practices across the county’s courtrooms, where the details of cases are often cast more in shades of gray than black or white.

Rollins unsettled law enforcement officials by declaring that her default policy would be to not seek charges for 15 lower-level offenses that she said too often end up being entry points for a downward spiral of involvement in the criminal justice system. In recent weeks she has tempered the pronouncement, which seems to be more work-in-progress than settled policy.

Rollins has a penchant for speaking her mind, a trait that can be a double-edged sword. It helped her make a mark on the campaign trail, but following her victory it has also been the cause of friction between the soon-to-be DA and those she’ll have to work with.

Rollins is quick to remind people that she doesn’t report to the police and, in part, will serve as a check on their behavior. Still, she needs to strike a balance in forming a cooperative relationship with law enforcement agencies her office will rely on to make cases, while living up to the reform agenda that led voters to make her the first woman ever elected Suffolk County’s chief prosecutor.

“She’s going to be building this bridge as she’s crossing it,” says Rahsaan Hall, director of the Racial Justice Program at the ACLU of Massachusetts.

“We’re at a moment in time where voters and communities are recognizing the prior tough-on-crime approaches haven’t worked,” says Miriam Krinsky, a former federal prosecutor who now directs Fair and Just Prosecution, a national nonprofit that brings together reform-minded prosecutors to share ideas and best practices. “I think she’s bold and willing to hit the reset button and do things differently, and not afraid of the fact that there may be some pushback,” Krinsky says of Rollins, who was part of an early December meeting of prosecutors the group convened in Houston.

“I report to the voters,” says Rollins, “and they spoke really loud and clear about what they want, and it’s change.”


Rollins spent four years in the US attorney’s office, most of it working on civil cases, and she never had a single-minded goal of becoming a DA or top prosecutor. As the oldest of five children, though, she says she’s always carried a passion for fair play. Her father is a second-generation Irish-American who grew up in public housing and went on to teach for 40 years in the Boston public schools. Her mother is the daughter of immigrants from Barbados and worked as a school nurse for 20 years in Boston schools. “I identify as a black woman, but I am fluent in many cultures,” Rollins says.

“What I learned in that moment was lawyers matter,” Rollins says of the battle to reinstate the UMass women’s lacrosse team when she was an undergraduate there. (Photo by Llyr Johansen)

She attended Buckingham Browne & Nichols, a Cambridge private school, thanks to a financial aid package. She was a standout lacrosse player, which helped her win a scholarship to the University of Massachusetts Amherst. After her freshman year, however, the university cut the national champion women’s lacrosse team, while the long struggling men’s football team was untouched.

“I didn’t know any lawyers. We didn’t have any judges in our family. But I knew what was fair,” she says. “As the oldest of five you always know what’s fair.” Rollins and a couple of teammates found a lawyer to take on their case and they threatened the university with a Title IX gender discrimination suit, a move that led to the team being reinstated.

“What I learned in that moment was lawyers matter,” she says, crediting the experience with putting her on a path to pursue a career in the law.

She’s had a varied legal career, which, in addition to her time as a federal prosecutor, has included four years in a big downtown Boston law firm, and stints as general counsel to the state Department of Transportation and MBTA as well as Massport.

In 2016, Rollins was diagnosed with breast cancer. She underwent a double mastectomy, surgery, and 18 months of treatment. Her preference for tackling topics directly extended to conversations with her then-12-year-old daughter, who asked if she was going to die. “I said, ‘I hope not, but we’re going to find out, and I will never lie to you about that,” says Rollins. The answer has been a good one, with Rollins declared cancer-free following treatment. “It changed me, for sure,” she says. “It slowed me down in a good way. There is nothing better than beating cancer to make you realize that nothing scares you and nothing is impossible.”

Rollins was candid during the campaign about her own family’s involvement in the criminal justice system, saying it provides another valuable dimension to her thinking on the issues facing a DA. Both of her brothers have served time in jail, and one is currently being held on a probation violation. A sister has struggled with addiction. Rollins also had her own early brush with the law, a charge of receiving stolen goods – a pair of sneakers – when she was 19, a case that was continued and eventually dismissed.

Along with her daughter, who is now 14, Rollins has custody of two nieces, ages 5 and 9, because of issues her siblings are facing. As if that didn’t put enough on her plate, until the campaign began, she was also on the Department of Children and Families list for emergency overnight placement of children deemed to be in imminent danger. Rollins estimates she had children stay overnight with her on 50 occasions over three years. Her parents, who are both retired, help her juggle it all, but Rollins admits to the classic traits of a first-born.

“I am a problem-solver,” she says.

In early December, Rollins was part of a panel discussion at Suffolk County’s South Bay House of Correction to mark its new wing dedicated to younger offenders, part of a trend toward separating these inmates and providing them greater access to education and rehabilitation programs. The last time she had been there was to visit her brother.

The bad choices her siblings have made are never far from her mind, she says. “It has been very apparent to me in my own family that decisions people make can follow them for the rest of their lives,” she says. “I will bring that to work with me every day.”


Rollins says she will work to end racial disparities in charging decisions, and she plans to undertake extensive training exercises with the DA office staff, including on implicit biases people may carry.

But the most tangible marker of the approach Rollins wants to take is the list of 15 charges for which she said the default position of the DA’s office will be to seek a resolution other than prosecution. The list includes such charges as shoplifting, drug possession, and malicious destruction of property. She says she’s willing to rethink aspects of the policy if there are “unintended consequences,” but maintains that this is the direction she wants the office to move in. “Of course, I want to have conversations with law enforcement,” she says.

The list drew a sharp rebuke from the president of the Boston Police Patrolmen’s Association. “I think that the quality of life is going to go down because she’s not going to prosecute these people and they are going to keep doing it,” Michael Leary told the Boston Herald following Rollins’s primary victory.  “Our job is already dangerous,” he told WBZ-TV. “It’s unbelievable to think people are willing to make it more dangerous for us.”

Rollins says she subsequently met with Leary and two other union leaders “There were some very good points that he made, and I asked him that it not be our last conversation and I don’t believe it will be,” she says, though they have not spoken since.

Leary did not return several phone messages. Boston Police Commissioner William Gross’s office also did not respond to multiple requests to speak with him.

More recently, Rollins has seemed to temper the policy, saying the approach will be not to seek incarceration for first-time offenders for the list of 15 charges, but she stopped short of saying they would not face prosecution. Details of exactly how her office ends up handling the cases are critical, since it’s not just jail time but a criminal arraignment that can follow someone and put a lifetime of hurdles in their path.

James Guido, the police chief in Revere, one of the four communities that make up Suffolk County together with Boston, Chelsea, and Winthrop, says law enforcement officials should use discretion in the case of young offenders without a record. “But to just have a no arrest or no prosecution policy – I don’t think that’s going to be productive,” he says. “There’s a lot of factors that need to be considered. I’m sure once she gets in office we’ll work together to come to a reasonable resolution for the police, the public that will work to make our communities safer and better.”

Suffolk DA candidates at Roxbury forum in June, from left to right, Rachael Rollins, Evandro Carvalho, Greg Henning, Linda Champion, and Shannon McAuliffe. (Photo by Michael Jonas)

Sen. Will Brownsberger, one of the main architects of the criminal justice reform bill enacted by the Legislature earlier this year, says he thought Rollins was sending a broad message rather than setting an ironclad policy. “I just took it in the spirit of generally we’re going to look at diversion when we can,” says Brownsberger, who endorsed Rollins in the Democratic primary. “I didn’t parse it more finely than that.”

“I think the election results and the votes that the Legislature took [in passing the criminal justice bill] speak to the same thing, which is the public wants us to lift people up instead of lock them up, when we can,” he says.

Former Boston police commissioner Ed Davis says his first reaction was to think of “all the people I knew in Roxbury and Mattapan” who struggle to keep their neighborhoods free not only of violent crime, but also of the kinds of offenses on Rollins’s list. “I think she’s trying to not use the criminal justice system as a hammer, and I’m all for that,” says Davis. But he says it’s important not to ignore minor offenses that also drag neighborhoods down. “Violent crime is certainly a big problem, but close behind that are quality of life issues people need help with,” he says.

The reality, say law enforcement officials, is that people rarely face jail time for the offenses on Rollins’s list, especially if it’s their first charge. “I think it’s sort of a move in the direction that has already been implemented in Boston,” Davis says of her goal, noting that the number of arrests fell each year of the seven years he was police commissioner, from 2006 to 2013.

Rollins says the Suffolk DA’s office has often been on the right track, but she wants to see a more systematic approach to diverting these cases across all courts in the county.

She says she met lots of people while campaigning who said they couldn’t get a laborer’s job because of a criminal record. “And you can’t walk 10 feet without hitting a crane in downtown Boston,” Rollins says, referring to the city’s construction boom. “It’s just heart-wrenching to me when I hear that.”

“There are too many cases clogging up the system where human beings are grist for the mill, largely because of poverty, substance use disorder, mental health, and trauma,” says Hall, the ACLU program director. “For her to address that, I think, is bold. What will be more telling will be her willingness to abide by that. The minute something happens where somebody who wasn’t prosecuted is involved in another crime, all eyes turn to this policy.”

“The statements I made I stand by. Whether that was the forum to have that discussion would be a different story,” Rollins says of a recent panel where she ruffled some feathers with Boston’s police commissioner. (Photo by Llyr Johansen)

While the controversy over the list of 15 charges has drawn a lot of attention, shifting the approach to justice will mean grappling with many other cases, including violent crimes, where the right thing to do isn’t always clear-cut.

In April, at the first candidate forum of the DA’s race, one of Rollins’s Democratic rivals, Shannon McAuliffe, a veteran defense attorney, recounted the case of a woman she once represented who attacked an MBTA bus driver. The woman had diagnosed mental illness, McAuliffe said, and was doing much better while on proper medication and in a program while out on bail. She said prosecutors insisted, however, on pursuing the charges, with her client ending up sentenced to six months in jail. McAuliffe said the woman lost her housing, was disconnected from her program, “and we all became less safe.”

It is a “sticky issue,” Rollins responded at the forum. “Yes, the prisons are becoming the new asylum, but we have to think really clearly and make sure victims are getting what they think is justice in the system as well.”

Rollins says that’s the sort of case that might be right for pursuing the expanded options for “restorative justice” included in the crime bill passed by legislators in April. Under that approach, if victims are willing, they are brought together with perpetrators in a session aimed at producing an outcome that helps repair the harm done to the victim and the community. “There has to be some middle ground,” Rollins says.


Danielle Williams is an organizer with the Massachusetts Communities Action Network, a coalition of faith-based groups that received grant funding in advance of the election to do outreach in Boston’s minority neighborhoods highlighting the important role of the district attorney. The ACLU of Massachusetts, which had conducted a poll showing 38 percent of Massachusetts voters did not even know DAs were elected, also mounted a public information campaign stressing the extraordinary power of the office.

The faith network’s phone canvassing efforts reached more than 14,000 Boston residents who were deemed the least likely to vote in the September primary – people from the age of 18 to 35 who had only very sporadically voted in past elections. The group also did street-level outreach, visiting barber shops and other places to talk about the DA’s race. Williams says organizers often brought a poster-sized map, based on a 2016 MassINC research study, showing the heavy concentration of homes in Boston’s minority neighborhoods that had a family member who had been incarcerated.

“Some people actually cried,” Williams says, when they saw the map.

She says Rollins’s election has been widely heralded in heavily minority neighborhoods most affected by crime. “I think people are viewing her as a breath of fresh air,” she says. “There’s a lot of hope in her.”

Williams, whose son was wounded in a shooting 12 years ago that has never been solved, says the DA’s office can help restore trust in the system. “They’ve got to be able to bridge that trust between the community and law enforcement,” she says.

“People are questioning police actions, they’re questioning the number of people of color who are incarcerated,” says Davis, the former Boston police commissioner. “We need to reestablish the trust for police, for the courts, for the prosecutors.”

Rollins has made that a top priority. She said throughout the campaign that minority neighborhoods suffer from being both overpoliced and underpoliced. She says there has been too much focus on lower-level crimes that saddle young people with records that make it hard to move ahead in their lives, while residents are frustrated that homicides and other violent crimes go unsolved. She regularly cites a Washington Post report that found Boston has the biggest racial disparity of any US city in homicide clearance rates, with murders involving a black victim resulting in arrests at a far lower rate than those in which the victim was white.

But as she prepared to take office, her effort to draw a range of voices into her transition team included one who offered an uncertain message when it comes to solving cases.

Christian White, who has served state and county sentences, is now active in promoting anti-violence efforts. In a YouTube video posted in October, however, he stood on a Mattapan street corner where a murder had recently taken place and offered a primer on the difference between a witness and snitch. In the video, which was taken down earlier this month, White explained that witnesses are everyday citizens who can be expected to look to law enforcement for help, while a snitch is someone who agreed to the “rules” of the street, which dictate never giving up someone else who also operates outside the law.

Gangs are often “taken down from within,” says one Boston community leader who works to curb youth violence and counsels at-risk youth. Anything that pushes back against gang members striking deals in exchange for testimony, he says, “short circuits our entire criminal justice system.”

Rollins has said she wanted a diverse group of 30 or 40 people on her transition team, including, she said in a recent radio interview, having “people closer to the problem helping us with the solution.”

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Michael Jonas

Executive Editor, CommonWealth Beacon

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