Rollins draws on wealth of experience: Work as lawyer, experience with family in justice system inform her approach

The Suffolk County Superior Court. (BU News Service File Photo)

By Allison Miller
BU News Service

This article was previously published in the Bay State Banner. 

At the downtown pub aptly-named Democracy Brewing October 22, a suit-clad crowd full of lawyers and other civic professionals stood attentive as 47-year-old Rachael Rollins rallied her supporters by talking about her “superpowers.”

“My superpower is that I have a spine of steel,” said Rollins, candidate for Suffolk County district attorney. “One of my other superpowers is loving making people uncomfortable.”

As the Democratic candidate, Rollins will likely make people uncomfortable if she beats out Republican Mike Maloney on November 6. Her now-famous list of 15 petty crimes she will not prosecute as DA, which includes instances like trespassing and disorderly conduct, gained support from President Barack Obama and The New Yorker magazine while drawing criticism from Boston police and local newspapers.

But if Rollins’ history shows anything it’s that she knows how to work her influence. If she does succeed Nov. 6, Rollins’ win will be a symbol of victory for not just herself but many people of color — and for women. She’ll break barriers as the first person of color DA in the history of Massachusetts and the first woman of color DA in Suffolk County.

On the campaign trail

Sitting in the publicly visible WGBH sound stage of the Boston Public Library six weeks after the primary, Rollins looked tired. She sipped a water and frowned down at her phone. Since winning the primary on September 4 by almost 40 percent in the five-candidate race, she hasn’t slowed down.

She came alive, though, when the Boston Public Radio show began on Friday, Oct. 19.

Rollins was fierce, answering tough questions about her platform with strong answers and a finger pointed at her interviewees, prompting host Jim Braude to joke about Rollins coming to prosecute him. When the show finished, Rollins got a round of applause from the live library crowd.

“The reason I think it went incredibly well is I did a lot of research beforehand,” said Rollins after the show in the lobby of The Lenox Hotel directly across the street. “Because the public deserves that.”

Although this would be Rollins’ first time in public office, she’s prepared well for these interviews thanks to her years of schooling, first at UMass Amherst and later studying law at Northeastern University. Notably, while an undergrad at UMass on the lacrosse team, she was  introduced to law through a Title IX lawsuit she and her teammates brought to the school after budget cuts shut down all of the girl’s teams schoolwide — but not the boys’ teams.

The lawsuit the lacrosse team brought resulted in all UMass women’s teams being refunded and reinstated. From there, Rollins got her law degree from Northeastern, her master’s from Georgetown University, and later attended a six-month leadership intensive program at Harvard Business School.

“What I want is to make government exceptional. I want to make us — even though we are the only place people can go when a crime is committed — feel like they can get justice,” Rollins said.

One way she knows how to lead an initiative like this is thanks to her time at Harvard Business School; there, she explored ways to best incentivize people without competitors, such as when they have a monopoly on something, much like the government does.

This transitions well into Rollins’ desire to run her office like a CEO. If she wins the bid for DA, she said she plans to teach competitive values to the hundreds of employees in the office. She’ll also use her legal experience working for the National Labor Relations Board of Boston, law firm Bingham McCutchen, as a DA in Plymouth County, and assistant attorney at the United States Attorney’s Office in Massachusetts. In addition, Rollins will use her leadership experience, most notably at MassDOT and the MBTA, where she was appointed chief legal counsel and managed a team of over 150 people.

Family influence

Rollins’ connection to her family shaped her platform in several ways. The oldest of five kids, she had a diverse childhood growing up in Cambridge, Massachusetts, the daughter to Irish-American and West Indian parents.

But now, some of Rollin’s siblings are incarcerated and some are struggling with addiction. Through these challenges, as well as professional experience, Rollins said she’s grown frustrated with the inequalities she sees in the criminal justice system.

“Overwhelmingly, [those working in criminal justice] criminalize poverty, mental illness and addiction” said Rollins at the Democracy Brewing event. “Our first inclination is not going to be prosecution … There’s so many other ways we can hold people accountable. Why are we holding them accountable for health issues or penalizing people because they are poor?”

Instead, Rollins is an advocate for restorative justice, like her colleagues Philadelphia District Attorney Larry Krasner and Chicago DA Kim Fox. Rather than criminalization, these city DAs want to offer alternative responses for convicts, such as rehabilitation and early education.

There are another 20 or 30 DAs of the 6,500 nationwide with a stance like this. But, Rollins said, it feels like she’s the only one here in Boston. In one article, a Boston defense attorney, alongside members of the BPD, called her list “a recipe for disaster”.

Despite this negative feedback, Rollins has continued to gain support, and pulled out a strong win in the primary. She said she was surprised at the large margin by which she won. Though polling results were released throughout the day, Rollins told her team not to provide her with updates.

At “every polling place, I wanted to be upbeat,” Rollins said. “I wanted to hungry, to meet voters and get votes.”

Overcoming the odds

At the Lenox after the recent WGBH recording, Rollins recalled walking into her office on election night and seeing mascara running down her campaign manager’s face. Rollins said she thought the worst before finding out that she’d won in districts like West Roxbury, where she had no expectation of winning.

Rollins said she remained skeptical of victory until the very end, even as her fellow Democratic candidates called to concede.

“My campaign manager came up and said Greg Hennings is on the phone. I was like, ‘Oh my God.’ He concedes, and then Shannon [McAuliffe] concedes. I still didn’t believe it,” Rollins said. “Then, Linda Champion called, and I was like, ‘Alright, I don’t think they are like conspiring to do this to me’.”

This is not the first time Rollins has overcome negative odds. A little over two years ago, Rollins learned she had breast cancer. Like many other women suffering with the disease, Rollins had five or six doctors’ appointments a week. She did it all while raising three children.

Rollins recalled having to tell her 12-year-old daughter, “I love you. I’m never going to lie to you about this. This is really scary,” she said. “My ex-husband is an amazing dad and he was wonderful. My family is awesome but they have seen me there, and now here.”

This June marked two years since Rollins was diagnosed, treated and then announced as cancer-free.

Nichelle Sadler, one of Rollins’ election volunteers, talked about Rollins’s ability to have similarly tough conversations with people while campaigning.

“She never backs down from a conversation. Her message is consistent,” said Sadler. “She understands what success looks like.”

Rollins said it’s her experience with breast cancer that fired her up for the decision to run for DA, to become the first person of color in the state as DA. It’s also what gave her that unstoppable “So what?” attitude.

“When you’ve survived something that kills so many people every year, nothing is impossible for me,” Rollins said. “I’d love to say, like, I want to run a marathon, too — but I also really love snacks.”

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