Politics

The Law According to Rachael Rollins

The charismatic new district attorney is Boston's greatest hope to bring the criminal justice system into the wide, woke 21st century. What's at stake? Only the future of law and order in our city.


Portrait by Diana Levine

The first thing I notice when I walk into Rachael Rollins’s downtown corner office is the impressive wraparound windowsill jam-packed with plaques, diplomas, statuettes, and a little engraved glass prism that catches the afternoon light shining through the window. Everyone from Mayor Marty Walsh and Massachusetts Lawyers Weekly to the Cambridge branch of the NAACP and a Dorchester football team has contributed an object to her collection.

“Wow, you have a lot of awards,” I say.

“See,” Rollins says, looking up from her desk. “There are people who like me.”

The second thing I notice is that the city’s top prosecutor is already on the defensive.

At first blush, it seems a little odd that the woman who recently won a landslide election with 185,133 votes (a number she mentions with striking regularity) would feel the need to remind me that there are people who actually like her. Then again, ever since winning the job of Suffolk County district attorney on a promise to reform criminal justice, reduce racial biases in the system, and essentially reinvent the role of DA, Rollins has become a lightning rod for Boston’s law enforcement and political establishments. She has received more attention and public ridicule than any other DA in the state—probably more than all of the rest combined—for policies her critics warn are a threat to public safety. She has taken heat from the cops, feuded publicly with Governor Charlie Baker, and been hammered by a fellow DA. She’s also been thumped by her fellow progressives for not yet making good on some campaign promises and has been featured in more unflattering photos in the Herald than she has spent months on the job. And she’s losing experienced prosecutors by the droves.

All of this adds up to the most excitement and commotion Boston has seen over the district attorney in as long as most people can remember. Then again, this isn’t a DA like any we’ve ever had. Not only is Rollins the first woman to hold the office in Suffolk County, she is the first woman of color to hold it anywhere in the state. She has the politics of a public defender, street cred in poor and crime-ridden communities, and truckloads of charisma. She isn’t afraid to defend herself, even if it means making it personal. She doesn’t have much experience as a county prosecutor but does have another kind of experience with law enforcement—she’s a former assistant United States attorney with siblings who have been on the wrong side of the law. She begins a remarkable number of sentences with the words “very candidly,” which is almost a joke because at this point no one expects Rollins to be anything other than utterly frank. After all, she says, she doesn’t have time for nonsense. “I believe we’re 40 years behind where we need to be in the criminal justice system. And I have four years in my term,” she says. “This is urgent for me.”

Rollins is already shaking things up. She’s hired a data scientist to analyze past performance and measure the impact of new policies, something she says no other DA in the state is doing. In what is thought to be a first in the nation, she has named an external committee to review officer-involved fatal shootings instead of letting prosecutors, who work with police on a daily basis, investigate these events. She is working to expand programs that use alternatives to criminal prosecution and has vowed to make solving the 1,000 cold-case murders in Suffolk County a priority. But it is her marquee policy of not prosecuting a slew of low-level offenses, which she believes criminalize poverty, addiction, and mental illness and disproportionately target black and brown people, that has most rankled her critics. Rollins counters that the prior administration wasn’t prosecuting many of the same crimes—she just formalized the practice so that justice could be applied equally to all defendants. The real reason she is being attacked, Rollins and other observers insist, is because she is a woman of color sending a very candid message to the establishment: Time’s up on the status quo.

After more than six bruising months of public battles and internal office problems, it’s not clear whether Rollins’s enemies will relent long enough for her to do her job or successfully implement her vision for change. Just don’t tell her it’s not personal. Whether it’s attacks on her, the attacks she makes on others, her politics, or even the reason why she decided to run for DA, everything for Rollins is, and always has been, very personal.

Rollins is only 5-foot-3 but cuts an imposing figure—and it’s not just because the stilettos and high-perched bun she favors easily give her an extra 6 inches. It’s because she comes off as tough as nails. Still, nearly everyone I spoke with, even those who think she’s doing a crummy job as DA, said Rollins is funny. Like, really funny. So when we sat down to chat, I told her I was wondering if she was going to make me laugh. She explained, in a delightfully dry tone, that it was a distinct possibility.

As we talked, Rollins shared how she decided to run for DA. She told me of the day in 2016 when she was diagnosed with breast cancer, and the surreal, dizzying moment when one second she had a perfectly normal life and the next doctors were talking to her about stages, percentages, and treatment options. “I took a deep breath,” she said—and so did I, leaning forward in my seat to hear Rollins reveal something heavy—“and I told them: I want pornography-quality breasts. Like up here,” she said, motioning with her hands to somewhere near her shoulders. “Like, I want them aiming backward.”

It was 12 minutes into the interview, and I was already laughing out loud.

Joking aside, she told me, her brush with mortality, combined with her increasing frustration with racial disparities in criminal justice, inspired her initial thoughts about running for DA. But to fully commit, she said, she needed a sign.

She found that sign at the bottom of a water slide in Florida. Rollins was attending spring training with her sister, Rebekah Salwasser, who directs the Red Sox Foundation, when she hurtled down the slide with her daughter, got out of the water, and checked her phone. She had dozens of voice mails, emails, and texts, all with the same message: District Attorney Dan Conley just announced he’s not running for a fifth term. You should.

One of the foremost reasons that early supporters thought she should run is the rare mix of personal experiences she could bring to the campaign trail. The eldest of five children of a mixed-race couple, Rollins identifies as black but, thanks to her father, says she is “fluent in white Irish male.” She grew up with tight finances in a working-class family, but a scholarship allowed her to attend school at the tony Buckingham Browne & Nichols. “I am everything that people don’t think I am,” she tells me, “and that’s my superpower.”

Race and class aren’t the only divides Rollins has straddled in her personal life. On one hand, she is an accomplished lawyer who worked at the U.S. attorney’s office and served as general counsel at Massport and the MBTA. On the other hand, one of her siblings has served time in federal prison on drug and weapons charges. And Rollins is candid when talking about how another has had his own run-ins with the law, and a third has battled an opioid addiction. As the result of some of these entanglements with the criminal justice system, Rollins is the guardian and has custody of two of her siblings’ children, in addition to having her own teenage girl. It was these contradictions that made her the most distinctive candidate vying for the job of the county’s top law enforcement officer. “There is no one out there with such a wide range of experiences,” Boston City Council President Andrea Campbell told me, explaining why she was one of those dozens of people who flooded Rollins’s phone with messages urging her to run. “She gets the story from both sides.”

From the start, Rollins faced an uphill battle. Five Democratic candidates were duking it out and one of them, Greg Henning, had the endorsement of Conley, the outgoing four-term DA, as well as the police unions. It was a foregone conclusion he would win. But the winds of change were in Rollins’s favor. For decades across the United States, DA candidates employed the same ol’ tough-on-crime platform and, once in office, measured their success in conviction rates. Over the past few years, though, as the nation has grappled with mass incarceration, racial biases in the system, and mounting research showing that high incarceration rates are actually counterproductive to public safety, voters everywhere from Harris County, Texas, to Brooklyn, New York, have elected DAs who have vowed to reform a broken system.

Rollins, like many of the progressive prosecutors across the country, and even some of her opponents in the race, vowed to stop criminalizing poverty, addiction, and mental illness; end cash bail; and send drug users to treatment, not jail. Then she went even further by releasing a list of 15 specific offenses—including shoplifting, trespassing to seek shelter, and disturbing the peace—for which the default policy would be not to prosecute unless extenuating circumstances existed.

Rollins’s personal story and her recipe for radical change resonated with voters, who rewarded her with 39 percent of the vote in the primary and 73 percent in the general election. “I think Greg Henning would have moved the office forward in incremental steps and in the name of preserving preexisting relationships,” says Adam Foss, a former Suffolk County assistant district attorney who considers himself a close friend of both Rollins and Henning and who works across the country advising reformist DAs. “But that’s not what the city of Boston needs right now.”

In no time, those long-standing relationships that Foss referred to started to crumble. The Boston Police Patrolmen’s Association criticized Rollins’s plan and predicted it would make the city less safe. The National Police Association called her policy ideas a “clear and immediate danger” and filed a complaint against her with the Massachusetts Bar. Even the then-president of the National District Attorneys Association predicted her proposed changes would lead to an increase in violent crime. Meanwhile, inside her office, assistant district attorneys started circulating their résumés and preparing their exits.

When Rollins strode into the DA’s building on January 3 for her first day of work, she found the doors to her office were locked. No one could find the key.

If Rollins can’t avoid the urge to make things personal, it might be because for her the attacks are not about policy but about who she is.

The attacks began in earnest roughly 10 weeks after the election, and it’s not entirely clear whether Rollins’s policies, or Rollins herself, was the intended target. In late March, the new DA released her long-awaited policy memo, a 65-page, data-driven document spelling out in greater detail the reforms she’d campaigned on. Just over a week later, Thomas Turco, the secretary of Governor Baker’s executive office of public safety and security, released a letter to the media—before Rollins had a chance to read it—blasting her new plans for not sufficiently taking into account public safety and potentially jeopardizing ongoing efforts to battle the opioid crisis. The phones in Rollins’s office started ringing off the hook with reporters requesting her reaction.

At a press conference the next day, a visibly upset Rollins came out swinging. First, she defended her policies and efforts to reduce racial and economic disparities in prosecution. Then she made it personal, throwing a punch that many argued landed below the belt. “Not everyone gets the benefit of the Baker family when they have interacted with the criminal justice system,” she said, referring to allegations that the governor’s son had groped a woman on a flight. “They don’t get to not get arrested, have the state police that reports to them handle the investigation, etc. Most moms that are living in Suffolk County don’t have a $1,000 lawyer to handle a charge.”

Baker’s office immediately leapt to the moral high ground, pointing out that “the administration does not engage in personal attacks.” Later, the governor called Rollins to apologize and told reporters the two had agreed to hit the reset button. But the next day, the imbroglio took a hairpin turn when Rollins supporters held a rally for her in Dorchester and she described to the crowd her interpretation of her highly criticized reaction to the Turco letter. “This is an example of when someone slaps you in the face and thinks you’re going to turn away and cry, and you take your earrings off, roundhouse-kick them dead in the face, and then punch them to the ground,” she told her cheering supporters.

Rollins’s next big battle happened about a month later, with Michael O’Keefe, the longtime district attorney for the Cape and Islands. In late May, he wrote an op-ed for the Boston Globe in which he didn’t name Rollins specifically—but clearly was writing about her. He derided “social justice district attorney candidates” and encouraged them to “work in the community” and leave the prosecuting to “professional prosecutors.” His piece even contained some thinly veiled racist thinking, noting that when it comes to racial disparities, it’s easier to blame the criminal justice system than it is to blame “the disintegration of the family, a lack of respect for discipline and education, and the glorification in some communities of a culture that celebrates disrespectful language and misogyny under the guise of art.”

Initially, Rollins stayed quiet, perhaps having learned her lesson from her earlier spat with Baker. When she appeared days later on WGBH’s Greater Boston with Jim Braude, she answered Braude’s questions calmly and, as always, confidently. In a matter-of-fact tone, she simply said O’Keefe was entitled to his opinions. She seemed seconds from a clean getaway when, after a photo of a much younger O’Keefe appeared on the screen, her face went from all business to something that bordered on an impish grin. “That’s a great photo of him,” she quipped. “It’s about a hundred years young.”

If Rollins can’t avoid the urge to make things personal, it might be because for her the attacks are not about policy but about who she is. After all, she said at the press conference about the Turco letter, “the men who were in this position before me were treated with quite a bit more respect.” She makes no bones that she believes the attacks on her are motivated by racism and sexism. Indeed, it is highly unusual, if not unheard of, for the governor’s public safety secretary to send a letter like he did to the press before communicating directly with the DA, or for a sitting DA to publicly criticize another DA. And other activist district attorneys, such as Philadelphia’s Larry Krasner, have not faced the same vitriol as Rollins. “Larry Krasner is like this super-radical guy who gets people’s backs up against the wall and he’s not receiving death threats like Rachael is,” says Foss, who has worked with progressive DAs across the country, including Krasner, and thinks Rollins is being singled out for criticism. “She’s getting a lot of mansplaining and is being dismissed. To put a finer point on it, there’s a lot of racism and misogyny that Rachael is dealing with.”

Rollins is also drawing fire from her own side of the political divide. While generally happy with the progressive DA’s performance thus far, Rahsaan Hall, director of the Massachusetts ACLU’s Racial Justice Program, said he was disappointed Rollins hasn’t fulfilled her campaign promise to appoint people of color to powerful positions within her office. (Since then Rollins has appointed an Asian-American woman, Amanda Teo, to be her chief of staff.) Meanwhile, the leftist CourtWatch MA, which has been monitoring activity in the courts, found in its report on the first 100 days of Rollins’s term that her assistant DAs were still prosecuting defendants for crimes on her list of 15 banned charges. In the weeks after the report came out, Atara Rich-Shea, the group’s cofounder, told me they’d seen some anecdotal evidence of improvement, but that Rollins’s policy was still not being implemented in many cases. Even the once very friendly Globe questioned her policy and early record as DA.

The frequency and variety of criticism thundering down on Rollins has some observers, such as Northeastern University law professor Daniel Medwed, concerned that her attackers aren’t giving her the opportunity to do her job. “She has only been in office for, like, six months and the knives are coming out from the left and the right,” he says. If the attacks continue, he adds, “It is going to be really hard for her to implement her vision.”

Rollins’s daily schedule is packed with speaking engagements, including this speech at the annual Martin Luther King Jr. Convocation at the Twelfth Baptist Church in Roxbury. / Photo by Nathan Klima for the Boston Globe/Getty Images

As I prepared to write this profile, I told Rollins’s deputy press chief, Renee Algarin, that I wanted to shadow the DA and see her do what she does around the office. Algarin reeled off a list of speaking engagements Rollins had in the coming days, including a graduation address at Boston Tech and short remarks at Mass General.

“Right, those sound interesting,” I said, politely, “but I need to see her in action, doing what she does as a DA.”

“This is what she does,” Algarin said. “Her calendar is full of speaking events.”

While it is safe to say Rollins is taking personal hits, her active speaking schedule is one of the reasons there is a perception that the DA’s office is starting to look a lot like the Rachael Rollins Show. “There’s a sense in the office that she cares more about her perception in the media than about doing the work,” said one assistant DA, who asked to remain anonymous for fear of reprisal, adding that it often seems like Rollins views being DA as “a stepping-stone for some other political office.” Some former staffers agree, one even calling her an “absentee landlord.”

Since taking the helm, she has spoken at or gone to receive awards from the YMCA, the NAACP in Providence, a veterans’ group at Boston’s Elks Lodge, multiple high school graduations, and a group of female athletes from economically challenged schools, among many others. When Rollins talks, she has two major themes: bias in criminal justice, and herself. Her self-referential attitude can even be seen in a recent press release about winning an injunction in a lawsuit against ICE that she and Middlesex County DA Marian Ryan filed together. Rollins’s quote started out, “I am incredibly proud that after taking office on January 2, 2019, I was relentless in pushing this litigation forward.” In contrast, Ryan’s quote in the same release was more boilerplate political-speak, focusing on the issue at hand and not invoking the personal “I.”

Another criticism from several current and former prosecutors is the emergence of a chaotic, quasi-Trumpian office atmosphere. In addition to Rollins’s willingness to go personal in her attacks on critics, her use of more colorful language than many prosecutors are accustomed to hearing from a DA, and her often appearing to be campaigning for something, there has been turnover in key leadership positions without replacements for months.

To her credit, when Rollins took over she fired no one. And while in any transition—especially after a four-term DA—departures are to be expected, one current and several former staffers who have left in the past months say attorneys are exiting en masse. According to Rollins’s office, 19 DAs have left since her term began. But a current and a former staffer said at press time that another four had just resigned, including high-ranking prosecutors. Meanwhile, the former staffer said that eight prosecutors left between her election victory and the time she took office. This brings the total to 31 out of a staff of around 160 prosecutors. Rollins’s office says she has hired nine prosecutors who carry regular caseloads, but the current and former employees say the reduced staff has resulted in a punishing workload divided among fewer attorneys and that the staff senses that there is no plan to fix the problem. This has caused record-low morale inside the office, they say. One current staffer claims to know of more than a dozen assistant district attorneys who are currently looking for new jobs and thinks the situation could soon become untenable. There’s a widespread fear inside the office, the prosecutor says, that with so few hands on deck and with the office’s staff spread so thin, something could go terribly wrong in a major case. If it does, that could harm Rollins more than any of the battles she’s fighting outside the confines of her own office.

Rollins says improving office culture is a top priority and that she is proud of taking positive steps, such as removing the keycard lock off the door of the executive floor, establishing more family-friendly policies, and even telling her staff it’s okay to unionize so they can fight for higher salaries. When it comes to her public speaking habit, Rollins admits she’s at it a lot. “I have probably spoken at more events than my predecessor did in his entire [16-year] term,” she says—but not by way of an apology. “Education is one of the most important parts of my job.”

Some people agree. “The conversation about who is going to jail, which is people who are black, brown, and poor, really needs to be had,” says Suffolk County Sheriff Steven Tompkins. “A lot of people don’t want to have that conversation. She is putting the issue in all of our faces to say let’s really talk about it. Sometimes you need an agitator.”

Considering that public events are a lot of what Rollins does—as well as one of the reasons she was catching flak at work—I attended a few of them to see what I could learn.

At the Pride Parade, she led a delegation from her office while sporting a rainbow feather boa around her neck. As the crowds gathered, someone from a group of transgender marchers behind her shouted through a megaphone that “without black and brown trans people there would be no Pride,” in reference to the demonstrators at Stonewall.

“Oh my God, I think that’s my new best friend,” Rollins said, rushing off to introduce herself. Moments later, as they talked, she motioned to the posters being hoisted above the crowd of the many trans people who have been murdered. Later, as she marched with Mayor Marty Walsh and other politicians, she was the only one whose raised hands weren’t robo-waving the whole time but rather snapping and noodling as she danced to and enjoyed the music. Her bodyguard, walking beside her as she danced down Columbus Avenue, told me she’s “totally down to earth; she’s a real person.” Even a former staffer told me that Rollins was “hands down the funniest, most relatable, likeable DA” the staffer had ever met.

Despite the optics of a relentless speaking schedule, many of these events are a chance for Rollins to do something she doesn’t get much credit for: listen. At a town hall meeting in Chelsea this past June, she opened the floor to questions and, as happens at most community meetings I’ve been to, someone asked a random question that had absolutely nothing to do with the purpose of the meeting. But Rollins patiently listened to the man complain about housing prices before suggesting he speak with city council members there that evening who were better equipped to deal with his issue. “Rachael listens to everyone, from the janitorial staff all the way to her first assistant,” Foss says.

This includes her critics. She’s gone on shows with conservative hosts Tucker Carlson, Howie Carr, and Jeff Kuhner and recently went to speak to the police patrolmen’s house of union representatives. She joked to me that it was really the “house of pain” because she knows the police aren’t happy with her. Rollins attended, she said, because it is important for her to hear from the people who don’t agree with her—directly, face to face, and not through the media. The meeting went well, said her first assistant, DA Daniel Mulhern, who added, “It’s impossible not to like Rachael.”

At an event one afternoon for female athletes from underprivileged schools, Rollins sat on a panel and fielded questions from the audience. A young girl asked Rollins, who is a former UMass lacrosse player, how she dealt with men who didn’t respect her, either in her profession or in sports. Sometimes, the girl said, she’d work 10 times harder than the boys in class but no one wanted to listen to her.

“Yeah, we can fight to make sure they respect us,” Rollins said. “But I want you to respect yourself. When you start with this deep, pulsing piece inside of you, knowing how smart you are, how talented you are, how capable and able you are, you’re going to look at them and be like, ‘You’re a clown.’”

In the moment, it seemed as though Rollins had just described her path forward as Suffolk County DA. Perhaps her greatest weapon and chance at success lies not in her propensity to fight for respect but in her sheer force of personality, which is to say that if she is able to rout her enemies and remake criminal justice in Boston, it won’t be despite the fact that everything is personal with Rollins but precisely because of it.

After hearing Rollins’s words of encouragement, the girl started to cry, and, seeing her break down in tears, Rollins stopped talking and started crying, too. After the event ended, Rollins found the girl, put her arm around her, and scribbled a phone number on a piece of paper for her so they could continue the conversation.