The rise and fall of Rachael Rollins - The Boston Globe (2024)

Just months earlier, Rollins had been a relatively little-known lawyer — a former federal prosecutor and general counsel for the MBTA. But when the long-serving Suffolk district attorney, Daniel Conley, announced he would not run for reelection, Rollins jumped into the crowded Democratic primary to succeed him.

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On the campaign trail, she promised to remedy racial disparities in the criminal justice system and cut down on what she viewed as gratuitous prosecutions of low-level crimes.

Now, it seemed, everyone knew who she was and was celebrating her victory, dancing with her on stage.

“That’s when I remember thinking her career was about to take off,” said Robert Fisher, who had worked with Rollins when both were line prosecutors in the US attorney’s office.

He was right. Rollins would soon become a nationally recognized figure in a nascent movement to reform prosecutorial methods, and then would be tapped by President Biden to serve as US attorney for Massachusetts.

But what neither Fisher nor any of the other attendees could have imagined was that Rollins’s political career would collapse seemingly as swiftly as it rose.

On Friday, months into her tenure as US attorney, Rollins resigned, after two bombshell federal reports documented a multitude of “egregious” and “blatant” ethics violations.

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In the days since the reports were released, critics and supporters alike have pored over Rollins’s record, highlighting her successes and missteps, and reexamining warning signs that might have foretold her spectacular fall.

The story that emerges is one of an ambitious reformer intent on righting the wrongs of a justice system she saw as unjust, but also of a hard-charging political star who seemed to believe the rules of the system she sought to change did not — or should not — apply to her. It is a story of zeal and hubris, of a polarizing figure who’s beaten breast cancer, browbeaten adversaries, and defied political norms, but whose worst enemy turned out, in the end, to be herself.

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“I would have thought she would be able to stop where the line said, ‘Stop,’” said state Representative Russell Holmes, a Mattapan Democrat and Rollins supporter. “When you are the law, you certainly need to abide by the law. . . . Before she was the US attorney, she knew that she would be a lightning rod. That was a surprise, knowing that, that you cross that line.”

Rollins swept into office as Suffolk district attorney after a victory in a Democratic primary election. A single mother and a political newcomer, she defeated four other candidates, including the top choice of local law enforcement, Greg Henning, then an assistant DA.

And the work was personal to her. Two of her siblings had battled addiction or served time in prison and she became the legal guardian of their children.

Her victory came amid a wave of wins by progressive prosecutors, including Kim Foxx in the Chicago area and Larry Krasner in Philadelphia, who promised to shake up the oftentimes cozy relationship between prosecutors and police. This new generation promised to use the local prosecutor’s office to effect positive social change, not just as a punitive weapon to be wielded against criminal defendants, who, in big cities, are disproportionately Black and Hispanic.

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It was a heady moment in the annals of American criminal justice reform. Here was an opportunity, supporters cheered, not just to protest the system from the outside, but to transform it from within.

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Indeed, days after Rollins’s victory in 2018, former president Barack Obama threw his weight behind the nascent movement — and Rollins herself.

Addressing voters during a speech in Illinois, he said, “Do what they just did in Philadelphia and Boston, and elect state’s attorneys and district attorneys who are looking at issues in a new light, who realize that the vast majority of law enforcement do the right thing in a really hard job, and we just need to make sure that all of them do.”

Closer to home, though, Rollins had adversaries — or, at the very least, skeptics — from day one.

Police leaders and other district attorneys bristled at some of her boldest proposals. Chief among them: She issued a list of 15 crimes she said her office would, in most cases, decline to prosecute. They included shoplifting, drug possession with intent to distribute, and some forms of resisting arrest.

In April 2019, three months into her tenure, Baker’s public safety chief sent Rollins a letter criticizing the do-not-prosecute list and other policies.

The safety chief, Thomas A. Turco III, praised Rollins’s “efforts to think differently” about criminal justice, but said that some of Rollins’s policies “would, if implemented as proposed, put at risk” the state’s efforts “to combat the ongoing crisis of the opioid epidemic and substantially restrict government’s ability to protect victims threatened with serious crimes.”

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The letter prompted dueling public statements from Rollins and the Baker administration. Rollins charged that men in her position “were treated with quite a bit more respect,” and veered into other criticisms, including knocking the handling of a case involving Baker’s son A.J., who had been accused the previous year of groping a woman during a flight to Boston.

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The temperature appeared to cool after Rollins and Baker spoke on the phone.

But the détente didn’t take.

At a public event the following week, Rollins addressed the conflict before a crowd of supporters. “The governor saw this was not going the way he thought it would and he picked up the phone and now we are done with that,” she said. “We are not going to talk about that any more.”

Then she did just that.

“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,” Rollins said. The crowd erupted in applause.

“I will always fight for what is right,” she said.

The spat with Baker was emblematic of two tendencies that would run in parallel through the rest of Rollins’s tenure as district attorney.

On the one hand, she advanced bold reform policies that were lauded by progressives and, in some cases, lambasted by conservatives and law enforcement officials.

On the other, she attracted attention for a string of high-profile incidents that revealed her combativeness and, perhaps, lack of restraint.

To her supporters, Rollins delivered on the promises she made as a candidate. Under her leadership, the Suffolk district attorney’s office reexamined murder cases and dropped charges against defendants whose prosecutions were questioned by a new Integrity Review Bureau. She identified police officers who, she said, were questionable witnesses because of corruption or past misconduct, and added them to a database made available to the public.

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Rollins also vowed to elevate the oft-unglamorous work of reviving cold-case murders.

“Every time Rachael said, ‘I’m going to have a unit solving murders that have been unsolved for 20, 30, 40 years,’ that resonated in every room that I ever was in with her,” said Holmes, the state lawmaker.

But even as she delivered on her agenda, she frequently courted controversy.

In a May 2020 interview on “Boston Public Radio,” she blasted the state’s public defenders as “overwhelmingly privileged” and questioned their commitment to their clients. The broadside against lawyers who work for relatively little pay to represent mostly indigent clients was enough of a slap to attorneys whom Rollins’s office often faced off against in court.

But it was what she said next that ignited a firestorm.

Speaking to a frustrated caller — a criminal defendant who said his public defender had not returned a call — Rollins told the man to call her office. That suggestion was, as defense attorneys soon pointed out, a flagrant breach of norms.

While Rollins was still on the air, a woman who identified herself as a lawyer called into the show and explained that a criminal defendant should never be urged to call a prosecutor for legal advice.

Other scandals followed. In January 2021, then-attorney general and now Governor Maura Healey launched a review of an incident in which Rollins allegedly pulled her vehicle close to another driver, activated her blue lights and siren, and said, “You don’t want to try me today lady, you really don’t ... I will give you a ticket.”

When a TV news reporter approached Rollins outside her house and asked about the incident, Rollins threatened to have the journalist arrested.

“I’m dead serious. I will find your name,” she said.

Within weeks, Healey concluded Rollins, then a leading candidate for the US attorney job, had not committed a crime or civil rights violation in the driving incident.

By July, Rollins got other news: At the recommendation of Senators Elizabeth Warren and Markey, Biden had nominated her to be Massachusetts’ next US attorney.

Republican senators strongly opposed Biden’s choice. Before Rollins’s confirmation vote in December 2021, Senator Tom Cotton described her as “uniquely unfit,” based on her record of implementing policies he described as “pro-criminal.”

Her nomination was confirmed by the slimmest of margins. After a 50-50 party-line vote, Vice President Kamala Harris voted in favor, breaking the tie.

As US attorney, Rollins presided over high-profile cases in Massachusetts, perhaps none more so than the recent indictment of a Massachusetts Air National Guardsman accused of leaking classified government documents.

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But last summer, new trouble emerged. After Rollins attended a Democratic Party fund-raiser along with first lady Jill Biden, the Office of Special Counsel, a federal watchdog agency, launched an ethics investigation to determine if Rollins’s presence at the event violated the Hatch Act, which bars some officials from engaging in political activities.

Then, last Wednesday, reports stemming from two federal investigations documented wide-ranging ethics infractions, including Rollins’s attending the fund-raiser, lying to federal investigators, improperly accepting gifts and travel reimbursem*nts, and, most serious, attempting to swing the 2022 election for the next Suffolk district attorney in favor of her preferred candidate, Boston City Councilor Ricardo Arroyo.

The reports from the Office of Special Counsel and the Department of Justice’s Inspector General described the alleged conduct as “flagrant,” “willful,” and, specifically with regard to her election interference, an “extraordinary abuse of her authority.”

There is a line between the type of political activity that helped Rollins rise and the responsibilities of a US attorney that led to her downfall, a distinction Rollins’s lawyer acknowledged when he noted that she “moved from being an elected official with virtually no restrictions on her activities to the highly-regulated environment of the US Attorney’s Office.”

“Understanding that or embracing that difference I think she may have had some difficulty with, unfortunately,” said Andrea Cabral, a former state prosecutor who served as Suffolk County sheriff and Massachusetts secretary of public safety, who has watched Rollins’s career unfold. “The rules and standards for that office are longstanding; not discretionary or optional. She chose not to follow it.”

Since the publication of the investigations, supporters of the progressive prosecutor movement have been in a kind of mourning.

“We lost a champion,” said Joyce Ferriabough Bolling, a Democratic political strategist.

Rahsaan Hall, former director of the racial justice program at the ACLU of Massachusetts, said he fears Rollins’s conduct could overshadow her work to advance the reform movement and transform the Suffolk district attorney’s office.

“It’s unfortunate, because detractors to the movement and people comfortable with the status quo can look to her actions and misdeeds and point to it as justification for why we should not embrace these reform-minded practices and policies, and I think it’s unwarranted and unfair,” Hall said.

Anna Harvey, a professor at New York University, praised Rollins as a risk-taker and said her policy as district attorney against prosecuting low-level crimes seemed to be yielding benefits. An independent study she coauthored, based on data provided by Rollins’s office, found that defendants whose misdemeanor charges were dropped before arraignment were less likely to return to the criminal justice system with another offense.

Harvey said, “There’s nothing about what we learned this week” that changes their findings.

“That legacy on behalf of criminal justice reform,” added Bolling, “will live on no matter where she goes from here.”

Mike Damiano can be reached at mike.damiano@globe.com. Milton J. Valencia can be reached at milton.valencia@globe.com. Follow him @miltonvalencia and on Instagram @miltonvalencia617. Matt Stout can be reached at matt.stout@globe.com. Follow him @mattpstout.

The rise and fall of Rachael Rollins - The Boston Globe (2024)
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