Boston’s New DA Is a Black Woman Who Is Out to Change the City’s Racist Sentencing Disparities

Rachael Rollins is the first woman of color to take the position in Massachusetts.

Rachael RollinsDiana Levine

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Update (11/6/18): Rachael Rollins just became the first woman of color to be elected as a district attorney in Massachusetts. Taking 79 percent of the vote, she defeated Michael Maloney in the race to become the top prosecutor of Suffolk County.

It was an unusual scene: In a county jail in Boston, inmates sat face to face in June with a row of attorneys who wanted their votes. The attorneys were competing to become the Democratic nominee for Suffolk County’s top prosecutor, to lead an office that would seek to lock away others accused of crimes, and the inmates wanted answers: Why were so many defendants pressured to accept plea bargains instead of going to trial? Did the candidates think it made sense for jails to give medical marijuana to elderly inmates in pain, and what did they see as the best way to help someone struggling with an opioid addiction prepare to leave prison? 

It was the first time district attorney candidates in the United States had ever held a forum inside a house of correction, and Rachael Rollins, an underdog in the primary race, tried to connect with her audience. “I don’t look at you as defendants, like some up in here,” she said, adding that she had received a phone call that morning informing her that her cousin had died of an overdose. Three of her siblings had cycled in and out of prisons, too. “I look at you as possibly being my sister, my brother, my neighbor, people I go to church with.”

In a huge upset a few months later, Rollins beat the heavily favored, police-backed candidate in the Democratic primary in September. If she wins in the November midterms, against a white male candidate accused of domestic abuse, she would be the first woman of color to serve as a district attorney in Massachusetts, and one of three female DAs in the state’s history. And for the first time, Boston’s sheriff, police commissioner, and DA would all be black, in a city and state known for some of the nation’s worst racial disparities in criminal justice.

In Boston, while black people make up a quarter of the total population, they accounted for nearly 70 percent of individuals who were observed, questioned, or searched by the police in 2016. They are disproportionately charged, jailed, and denied bail. And crimes perpetrated against them aren’t investigated with the same rigor: The killing of a white person there is more than twice as likely to end with an arrest than the killing of a black person—a gap that’s unparalleled in other major cities, according to a Washington Post investigation. The Suffolk County district attorney’s office, held for the last 16 years by Daniel Conley, pitches in with some of these homicide investigations. It also decides when to press charges and which cases to drop, and it makes plea bargains that can affect defendants’ sentences.

Nationally, less than 5 percent of elected prosecutors are people of color. In Massachusetts, every single district attorney is currently white. And most run for office unopposed; Conley, who recently resigned, held his title for four terms without a challenger. But that’s beginning to change: Following in the footsteps of Philadelphia DA Larry Krasner and Chicago DA Kim Foxx, Rollins is part of a wave of more progressive candidates running this year who are hoping to disrupt the status quo by proposing ways to send fewer people to prisons and to do so more equitably. For her, that means not pursuing charges for many low-level crimes and prioritizing treatment for people struggling with addiction and mental illness. It also means using implicit bias training and restorative justice techniques, and bringing in outside prosecutors to investigate police misconduct—pledges that recently caught the attention of former President Barack Obama, who praised her in September for “looking at issues in a new light.”

Rollins, who took custody of her two nieces partly because of the opioid epidemic, has personal experience with the limitations of the criminal justice system. She knows firsthand what it’s like to have a rap sheet—she was accused of a misdemeanor 28 years ago when she was 19, a charge that was continued without a finding and later dropped, but which she says helped her understand the lasting impact of a record. “I come to this situation having seen the criminal justice system, I can comfortably say, from almost every single angle,” she tells me.

The oldest of five kids, Rollins grew up in Cambridge with her mom, an immigrant from the West Indies, and her dad, an Irish-American military veteran who served as a corrections officer before finding work with Boston’s public schools. She became interested in law after her freshman year in college when her lacrosse team and two other women’s teams were eliminated from the university because of budget cuts that didn’t affect any male athletes; she helped file a Title IX lawsuit to reinstate them. Eventually, she landed a gig as a labor rights attorney, later focusing on First Amendment cases, civil litigation, and criminal defense. She joined the US Attorney’s Office as a prosecutor and then became the first person of color to ever serve as general counsel of the Massachusetts Department of Transportation.

Despite her experience, she wasn’t immediately a consensus candidate for DA. “From a community perspective, a lot of people didn’t think Rachael would win,” says Monica Cannon-Grant, a progressive activist in Boston who works on violence prevention and trauma services. “We come from a community where the candidate who aligns themselves with law enforcement usually wins the race.” According to Cannon-Grant, the city’s police department donated tens of thousands of dollars ahead of the Democratic primary to the establishment favorite, Greg Henning, a veteran prosecutor. Still, Rollins took 40 percent of the vote in the five-way race, riding a wave that also carried other Boston women of color to victory, including Ayanna Pressley, who won a historic nomination for Congress, and Nika Elugardo, who won a seat in the state House. “One of our colleagues refers to her as Thanos, the Marvel Comics character that basically obliterated half the universe, because she just obliterated her competition,” says Elugardo, who campaigned with Rollins and describes her as “fierce” and “focused.” “She is intensely practical about what you have to do in the short term to produce long-term change.”

In November, Rollins is up against Michael Maloney, a 38-year-old defense attorney from Brockton who’s running as an independent candidate with police backing. He also wants to stop prosecuting nonviolent drug crimes and help people struggling with addiction get treatment—he owns an alternative wellness company and built a chain of medical marijuana evaluation facilities. But in many ways, he’s far less progressive: He recently accused Rollins of playing the “race card” to sway voters, and he described her attitude toward low-level offenses—she said she would generally decline to prosecute 15 of them, including shoplifting, trespassing, and disorderly conduct—as “crazy.” 

While Rollins’ campaign pledge could be described as unorthodox, her proposal isn’t exactly revolutionary. DAs don’t typically talk about it publicly, but their assistant prosecutors often decline to prosecute low-level offenses because they are bogged down with cases and need to focus their resources on more violent, serious allegations. Suffolk County is no exception. “But our sense is that there is a racial disparity, that more white people benefit from those nonprosecutions,” says Rahsaan Hall, who directs the racial justice program for the state’s ACLU, which does not endorse candidates in elections.  “Communities of color and poor communities are overwhelmingly overpoliced and overprosecuted, and it’s these types of low-level offenses that ensnare people within the system and make it difficult to move on with their lives.”

Massachusetts has the country’s second-lowest overall incarceration rate. But its sentencing disparity is pronounced: While black people nationally are locked up at six times the rate of white people, those in Massachusetts are locked up at about eight times the rate, according to the state Sentencing Commission. Latino people in Massachusetts are incarcerated at five times the rate of white people—four times worse than the national average. “Communities across Boston are saying clearly that they want to be policed differently, they want to be treated differently, and they want their kids to be treated differently,” says Jordan Berg Powers, who leads Mass Alliance, a Boston-based coalition of progressive political and advocacy groups that work on issues including civic participation.

Some change is in the works. Suffolk County Sheriff Steve Tompkins, who encouraged inmates to join the forum with DA candidates at the jail in June, took office back in 2013, and Boston Police Commissioner William Gross, the city’s first black police commissioner, was appointed this summer. And in April, Gov. Charlie Baker signed a 121-page bill—opposed by Suffolk’s outgoing district attorney—that overhauls the criminal justice system by, among other measures, eliminating certain mandatory minimum sentences, preventing kids younger than 12 from being charged in court, making it easier to expunge certain offenses, and improving conditions in jails and prisons. But other reforms have proved harder to push through: In recent years, legislative proposals to require independent investigations of police-involved shootings have gone nowhere. Rollins and Maloney have both pledged to bring in outside prosecutors when cops, who work closely with the DA, are accused of misconduct.

At the jail forum in June, Maloney also tried to use his background as a defense attorney to appeal to inmates. “I’ve never been a prosecutor,” he said. “I am an incredibly strong proponent of criminal justice reform.” But his pitch hasn’t always landed so well. Just days earlier, at another forum moderated by three New England Patriots players at a middle school, he was heckled when he spoke about his close relationship with law enforcement. “I don’t hate on police,” he said after a player asked about discriminatory policing. “I am very good friends with a number of law enforcement individuals.”

His campaign took another hit when the Boston Globe recently revealed that his ex-wife asked for a restraining order against him in 2014. According to court documents detailing three fights while they were married, he allegedly pushed her, smashed a chair and their oven, snatched glasses off her head and threw them across a room along with her phone, and threatened to slit her father’s throat. He later told the Globe he took “full responsibility for my actions,” and that he never hit her. “While at the end of the day I am human, no one should question my ability to manage my reaction to dynamic and intense situations or my ability to consistently make judgments on domestic violence cases or violence against women from this situation,” he added. No criminal charges were filed against him and the restraining order was eventually lifted.

After her strong showing in the primary, Rollins is optimistic about her chances in the midterms. “I am going to work really hard to make sure we are successful and we get to start talking about sexual assaults and domestic violence and crimes against women because they matter,” she told me. “Women’s perspectives matter. People of color’s perspectives matter. It’s important that we’re going to have a different voice at the table.”

Still, she’s not taking anything for granted. “I think if Maloney can make inroads with people in communities of color, he may have a chance, but I don’t know if capitalizing on the police resentment and law enforcement establishment vote is going to be enough,” says the ACLU’s Hall. “But this is Suffolk County and you never know.” 

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