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How much will incoming Suffolk DA Rachael Rollins shake things up?

Rachael Rollins joined Nativity Preparatory School students during mock trials at the Moakley Federal Courthouse.
Rachael Rollins joined Nativity Preparatory School students during mock trials at the Moakley Federal Courthouse.(Matthew J. Lee/Globe Staff)

QUINCY — Rachael Rollins stood before 50 union employees, many of them black and Latino, and revealed a provocative question she planned to ask prosecutors seeking to keep their jobs when she takes over as Suffolk district attorney.

“Why did you apply for a job where you would be putting people of color in jail every single day?” she said in late November, drawing loud applause from the staffers of the 1199SEIU United Healthcare Workers East who had gathered at their headquarters to hear her speak.

Two weeks later, Rollins was at the district attorney’s office in downtown Boston, addressing dozens of apprehensive employees, including prosecutors, many wondering if they would still have a job when she is sworn in Jan. 2

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Her message was warm and reassuring, recalled Bob Madden, a longtime investigator in the office.

“ ‘I want everybody here to relax,’ ” he recalled her saying. “ ‘Please don’t worry . . . for the most part, everybody is going to be fine.’ People walked out of there feeling pretty good.”

The disparate messages underscore the political tensions Rollins faces as she prepares to become the first woman and the second African-American to serve as the county’s top prosecutor. Because she was elected on a pledge to reduce prison sentences and stop prosecuting 15 low-level crimes, her ascension has raised apprehension in law enforcement circles and excitement among advocates who see her as a catalyst for reforming the criminal justice system.

The full scope of her agenda — and how aggressively she will pursue changes in the face of opposition and the practical demands of the job — has become a subject of intense interest in the legal community, and will be watched closely in the coming weeks and months.

As her inauguration nears, Rollins and members of her transition team have been meeting with dozens of the nearly 300 employees of the Suffolk district attorney’s office, which includes about 150 prosecutors. Essentially, they are interviewing to stay in their jobs.

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During her speech before the union, Rollins, 47, laid out her vision for the office. She pledged to assign more detectives of color to the homicide unit, place more women in top positions, and hire people of all ages — from millennials to seniors — for jobs such as secretary, investigator, and victim witness advocate.

“I want my office to look like this room,” Rollins told the union employees.

Larry Krasner, a longtime defense attorney who became Philadelphia’s district attorney earlier this year, fired 31 prosecutors his first week in office, a move he called critical to carrying out sweeping changes.

In an interview, Rollins answered carefully when asked if she would do something similar.

“There will be change,” she said. “It’s never easy, but it’s always required for growth, and I’m excited about the process.”

Rollins said she wants prosecutors who share her primary goals: changing the charging practices in juvenile and district courts and reducing the time people spend in prison. Rollins indicated she wants to follow Krasner’s decision to use manslaughter and second-degree murder charges in some types of cases that have been prosecuted as first-degree murders.

Rachael Rollins addressed middle school students who were participating in mock trials earlier this month.
Rachael Rollins addressed middle school students who were participating in mock trials earlier this month.(Matthew J. Lee/Globe Staff)

After Rollins won the Democratic nomination in September, police and others criticized one of her major policy proposals: not to prosecute first-time offenders for low-level crimes, ranging from shoplifting to resisting arrest to drug distribution. Rollins said many such offenders are poor, addicted to drugs or alcohol, or are mentally ill, and should instead perform community service or be sent to rehab programs. She pledged to work with police on implementing the policy.

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Boston Police Commissioner William Gross was not available to comment, according to a department spokesman.

Brian Kelly, a former assistant US attorney who became friends with Rollins when she was a prosecutor in the civil division, said that while he disagrees with her proposal not to prosecute certain crimes, he believes she will be a pragmatic leader.

Kelly, now a partner at Nixon Peabody in Boston, described Rollins as charismatic, intelligent, and funny, with an uncanny ability to mimic nearly anyone she meets.

“I think she will take an evenhanded approach, notwithstanding some of the rhetoric during the campaign that has some law enforcement people concerned,” Kelly said. “She’s very practical.”

She also has an intensely competitive side. When Greg Henning, the establishment-backed candidate in the Democratic primary, called her to concede on election night, she turned to her supporters and made a throat-slashing motion to signal the race was over.

“I could have Brandi Chastained it and ripped my shirt off,” Rollins quipped.

Rollins grew up in Cambridge, the oldest of three girls and two boys. Her mother, a retired school nurse who made her own salves and spices from herbs in her garden and kept bees in the backyard, is the daughter of immigrants from Barbados. Her father, an Irish-American Vietnam War veteran, worked as a guidance counselor in the Boston Public Schools and supplemented his income by refereeing high school and college sports games.

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They settled in Dorchester but in the early 1970s moved to Cambridge to escape the slurs and other racism they encountered as an interracial couple.

“They don’t really talk about it,” Rollins said. “I don’t think it was pleasant, I’ll put it to you that way.”

Rollins’s parents were determined their children would receive excellent educations and enrolled them all in private school, helped by financial aid. Rollins and three of her siblings attended the prestigious Buckingham Browne & Nichols school in Cambridge, where many students came from wealthy families. Bekah Salwasser, Rollins’s sister, said she was often too embarrassed to invite friends to their home, a nondescript house that had to be heated by a fireplace.

“I remember not wanting to invite anyone to our house, because it wasn’t big and it wasn’t full of nice things,” said Salwasser, now executive director of the Red Sox Foundation. “You’d go to school and someone’s Range Rover from their 16th birthday would be in the parking lot.”

Still, Rollins excelled at the school, Salwasser said, particularly at sports like lacrosse, soccer, and basketball.

Rollins received an athletic scholarship at the University of Massachusetts Amherst to play lacrosse, but the program was eliminated a year later. Rollins and a group of other students threatened to file a Title IX complaint against the school, and the program was reinstated. It was her first legal victory, in a way, and her impetus for going to law school, Salwasser recalled.

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After a stint at the Bingham McCutchen law firm, Rollins spent four years at the US attorney’s office then became general counsel for the Massachusetts Bay Transportation Authority and later chief legal counsel for the Massachusetts Port Authority. She left in 2015 to enroll in an eight-month Harvard Business School program. The following year, she was diagnosed with breast cancer and had a double mastectomy and other surgeries.

“I’m not afraid of anything anymore, because I survived breast cancer,” Rollins said.

In 2017, furious over the spate of police-involved shootings of black and Hispanic men across the country, she began thinking of running for district attorney.

During her speech at the union headquarters in Quincy, Rollins struggled not to cry as she described that decision.

“It really makes me sad as a leader to know that the system is not set up to help the people that need it the most,” she said, her voice just above a whisper. “And it is exactly why I said after raging in my home one evening . . . that I was no longer going to sit at home and cry or scream or swear.”

The struggles of her other siblings also served as motivation. While Rollins and Salwasser have risen to the tops of their professions, their sister is recovering from drug addiction and their brothers have cycled in and out of prison. One is serving a 15-month federal sentence for violating his probation on a firearms and heroin distribution conviction.

“I will never make excuses for them,” Rollins said. “You can love somebody but not be supportive of the choices they made.”

Salwasser said her sister’s decision to run did not cause tension in the family.

“If anything, people were really, really encouraged to see her stepping into this position,” she said. “I think we need someone who has had experience in this, someone who understands what it means for someone to go to jail.”

Rollins, who is the legal guardian of two of her siblings’ daughters, ages 5 and 9, also lives with her 14-year-old daughter, Peyton, her only child from a marriage that ended in divorce.

The family plans to move from Medford, where Rollins owns a house she will put up for rent, to Roxbury.

She and her transition team are still interviewing office employees. Rollins said many prosecutors she has spoken with are receptive and are already recommending lesser charges for serious crimes.

As for her question about putting minorities in prison, Rollins said she has found their answers reassuring.

“ ‘Of course that’s not why I took that job. I believe in getting justice for victims,’ ” Rollins said they have responded. “There is a deep compassion and honor in the people I’ve interviewed thus far in that office.”

Rollins, the granddaughter of immigrants from Barbados, helped unfurl the Barbados flag during a ceremony last month at City Hall.
Rollins, the granddaughter of immigrants from Barbados, helped unfurl the Barbados flag during a ceremony last month at City Hall.(David L. Ryan/Globe Staff)

Maria Cramer can be reached at mcramer@globe.com. Follow her on Twitter @globemcramer.