Prosecutors like Rachael Rollins won office vowing to fight the system; now, the system is fighting back

Powerful opponents claim that progressive prosecutors are improperly using their roles, and argue that their policies will drive up crime rates.

Suffolk District Attorney Rachael Rollins.

Prosecutors in Boston went to court days after the controversial “Straight Pride Parade” this summer with plans to drop some of the cases against counterprotesters, deeming one disorderly conduct charge “inappropriate.”

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When the judge pushed back, attempting to continue that prosecution over their objections, District Attorney Rachael Rollins publicly denounced him and appealed to the state’s high court. She won a judgment stating that Judge Richard Sinnott had overstepped his authority.

It was the kind of action Rollins had promised voters when running for office in Suffolk County, Massachusetts, last year, pledging fewer lower-level prosecutions as she took aim at the criminal justice system. That approach quickly propelled Rollins into the heart of a clash over the future of district attorneys, a remarkably public debate pitting law enforcement officials against each other across the country.


“We’re getting back to the work that the people of Suffolk County elected me to do,” Rollins told reporters after the high court backed her in September, “and changing a system that doesn’t work well for a majority of people that come into contact with it.”

Rollins is among more than two dozen recently elected prosecutors who are pushing progressive policies across the country — including in Philadelphia, Dallas and Orlando, Florida — and breaking from decades of tough-on-crime thinking. Progressive candidates are also on the ballot Tuesday in closely-watched prosecutor elections in Virginia and San Francisco.

Progressive prosecutors, as they are generally known, have been elected on platforms that included abandoning cash bail, declining low-level charges, not pursuing marijuana cases and closely scrutinizing police conduct, in efforts to reform a system that they say over-incarcerates and disproportionately punishes poor people and racial minorities.

They vowed to change that system, but the system is fighting back. Powerful figures — including lawmakers, governors, police union leaders, fellow district attorneys and Trump administration officials — have been sharply critical, with some saying progressive prosecutors are improperly using their roles to decline charges and arguing that their policies will drive up crime rates.

After Dallas District Attorney John Creuzot said he would not prosecute certain crimes, the Texas governor and attorney general accused him of promoting “lawlessness.” In San Antonio, District Attorney Joe Gonzales pledged to reject criminal trespass charges for homeless people, a decision that the police union assailed as “a total abdication of [a] D.A.’s responsibility, which is to hold the guilty accountable.”


In Philadelphia, where the district attorney directed prosecutors to seek less severe sentences and not impose charges for some offenses, U.S. Attorney William McSwain accused him of causing a “public safety crisis” there.

“The role of the prosecutor in America today is clearly to enforce the law and not to make the law and not to pretend that you’re a legislator,” McSwain said.

District Attorney Larry Krasner dismissed McSwain as an “attack dog” echoing rhetoric from President Donald Trump, who has criticized progressive prosecutors.

The country’s top law enforcement official also joined the fray. In an August speech to a police group, Attorney General William Barr called progressive prosecutors “anti-law enforcement” and “dangerous to the public safety.”

Their policies will have “predictable” results, Barr said: “More crime and more victims.”

Candidates for top prosecutor jobs have long campaigned as being tough on crime, an approach that had consequences, particularly for poor people and minorities, progressive prosecutors say.

“Disastrous policies have resonated for decades. . . . The old approach messed everything up,” Krasner said. “We ended up with a level of mass incarceration that makes us the most incarcerated country in the world.”

In response, many advocates for criminal justice reform have shifted their attention in recent years to top prosecutors, who are usually locally elected and wield remarkable power within the system. Prosecutors have discretion to decide who to prosecute, what to charge and, in many cases, can determine how cases are resolved, legal experts said.


“In cases that are plea bargained, which in this country are the vast majority of cases, the prosecutor decides what kind of plea bargain to offer or to accept,” said David Alan Sklansky, a Stanford Law School professor who wrote a guidebook for progressive prosecutors. “That means, as a practical matter, that the prosecutor is also often determining what the sentencing will be.”

Once in office, top prosecutors typically face little risk of losing their jobs, said Ronald Wright, a law professor at Wake Forest University. Wright studied district attorney races that unfolded in 10 states between 1996 and 2006 and found that 95% of incumbent prosecutors were reelected, with many facing no opposition.

Prosecutors like Rollins – who bested a crowded field last year after the incumbent district attorney decided against seeking a fifth term – are pushing what they describe as a holistic approach to criminal justice.

Violent criminals should be prosecuted, Rollins said, but she also believes more people should be sent to treatment and fewer put behind bars.

Part of her approach is about “focusing our limited resources” on more serious crimes and going after those, Rollins said, and showing respect to people no matter how they encounter the system.

“Today’s defendant is potentially tomorrow’s victim and was yesterday’s witness,” Rollins said. “And so, if I treat you horribly as a defendant but then want to be nice to you when you’re a victim or ask you to come forward when you’re a witness? People aren’t stupid.”

‘So-called progressives’

Rollins, who was raised in Cambridge, Massachusetts, developed her views about the justice system in part through her experience as a federal prosecutor in Boston. The system also touched her personal life; two of her siblings are incarcerated, she said, and a third is in recovery for opioid addiction. In addition to her own teenage daughter, she said, Rollins is the guardian for two nieces because of her siblings’ circumstances.


“I come to work with a very different lens every day,” Rollins said.

Her personal and professional worlds have collided in sometimes uncomfortable ways. In the fall of 2012, the year after she left the U.S. attorney’s office, Rollins was back in a Boston courtroom and saw a judge whom she had argued in front of before. Rollins said he greeted her with a smile before his expression changed.

“With a perplexed look,” Rollins recalled, the judge “tilted his head to say without saying it, ‘What are you doing here?’ “

His answer walked through the door: Rollins’ brother, handcuffed by U.S. marshals and facing drugs and weapons charges filed by her former office.

“It was an incredibly humbling moment,” she said.

Rollins took office as Suffolk County District Attorney in January, with jurisdiction over Boston and three neighboring communities. A few months later, she released a 65-page policy memo expanding on her campaign pledge not to prosecute what she called “low-level, nonviolent offenses,” including disorderly conduct, drug possession and resisting arrest.

These charges are frequently fueled by issues including poverty and mental health, her memo said, and are “best addressed through diversion or declined for prosecution entirely.” She noted some exceptions, including when a person poses a dangerous threat.

Her policies triggered criticism from the Boston police union and a fellow district attorney. Thomas Turco, the Massachusetts public safety secretary, released a public letter to Rollins, praising her “efforts to think differently about criminal justice” but saying these policies could hurt the state’s efforts against the opioid epidemic.


Rollins, the first black woman elected to her position, said Turco’s letter “never would have happened” if she were a man.

She and some other progressive prosecutors point out that many of them are women or people of color, while district attorneys are usually white men. They believe that factors into the criticism and say there is a benefit to expanding who holds these roles.

“When a diverse prosecutor sits in this chair, we should be expecting diverse thought as a result of diverse experience,” said Aramis Ayala, the progressive state attorney in Orlando, Florida.

Turco’s office did not respond to interview requests for this story. Through a court spokeswoman, Sinnott, the judge who objected to how Rollins’ office handled the “Straight Pride Parade” charges, declined an interview request.

“There are a lot of men that are very, very nervous about it because we’re looking at things differently,” Rollins said in an interview before her dispute with Sinnott. “And the system is now going to work the same for everyone, not just those that understand it or have access.”

Other prosecutors have also questioned her ideas. Michael O’Keefe, district attorney for the Cape and Islands in Massachusetts, took aim at Rollins’ policies and other progressive prosecutors in a Boston Globe op-ed lambasting what he called “social justice district attorneys.”

In an interview, O’Keefe praised Rollins personally and said his disagreement with her is solely about policy. Prosecutors already exercise discretion in cases, he said, but Rollins’s plans reach far beyond that.


“Our discretion operates within a . . . narrow set of circumstances having to do with the individual facts of an individual case,” he said. “We don’t have the discretion to eliminate an entire category of crime.”

O’Keefe said the way to reduce the number of people charged with crimes is to reduce crime, not prosecutions.

“The criminal justice system is an inert entity. It doesn’t go out looking for customers,” he said. “It sits there and customers are brought to it. And they’re brought to it because there’s probable cause to believe they’ve committed a crime.”

Rollins said her plans are no different from the discretion he and other prosecutors already use.

“There are thousands and thousands and thousands of laws on the books that we don’t prosecute,” Rollins said. She added: “It’s very interesting that there were very few articles about the discretion a D.A. has when we were on a freight train toward mass incarceration and racial disparities.”

Mike Hestrin, district attorney in Riverside County, California, said reform isn’t new to prosecutors’ offices, but he disputed that this is what “these so-called progressives” are pushing.

“I don’t see them as reformers,” Hestrin said. “What they’re after is to destroy the system, the criminal justice system, that they very deeply misunderstand. . . . This is not progressive. It’s not reform. It’s just, it’s politics and ideology-driven.”

Impacting crime rates?

In Philadelphia, the top federal prosecutor and district attorney have traded barbs since both took office last year, including arguing about that city’s crime rates.

Homicides went up last year in Philadelphia, the seventh time in a decade they increased, while overall violent crime decreased slightly, according to police statistics.


McSwain, the U.S. attorney, blamed Krasner, the district attorney, for the increase in homicides. He said his office shifted resources to charge more violent crime cases and that the crime numbers would be worse if he hadn’t acted.

Krasner called McSwain dishonest and emphasized the decline in violent crime despite the city’s “serious problem right now with shootings and with homicide.”

Opponents of progressive prosecutors often point to the potential effect of their policies on crime rates. Reform advocates say the warnings are fearmongering.

“All those prosecutors who say this is going to endanger our communities, have they been to our communities?” said the Rev. Mariama White-Hammond, a pastor and activist in Boston. “Those of us who live this reality know it’s a little more complex than the ‘lock ’em up’ policies that have been sold. I don’t believe those policies are working for our communities.”

Richard Berk, a statistics and criminology professor at the University of Pennsylvania, said it is too early to know how Krasner’s policies and those of other progressive prosecutors could be impacting crime rates.

“There’s a natural variation in things like homicide, natural in the sense that we don’t know what causes it,” Berk said. “And we basically try to treat it as noise and don’t try to tell a story until we have that nailed down.”

McSwain and other critics also have decried the support many progressive prosecutors have received from liberal megadonor George Soros, who has been funneling money into campaigns across the country.


“Especially on a local race, that’s going to have an effect,” said Duffie Stone, a prosecutor in South Carolina and president of the National District Attorneys Association. “You’re going to win some races if you put a lot of money into it.”

Whitney Tymas, who chairs the Justice & Public Safety PAC funded by Soros and others, said prosecutors “rarely face challengers” and that her group helps give “voters a real choice.”

“Critics use Soros to deflect attention from the reality that too many prosecutor elections are not competitive,” Tymas said in a written response to questions.

Scott Colom, a progressive district attorney in eastern Mississippi, said he benefited from unexpected Soros backing in 2015. He campaigned as a reformer, ousting a veteran prosecutor who had said at the time that Colom would be akin to another defense lawyer if he won the election.

Colom thinks grass-roots efforts, not big donations, are what help elect similar candidates. He pointed out that he’s running unopposed for a second term in Tuesday’s general election, something Colom attributes to the changing thinking around criminal justice.

In Boston, Rollins said she wants to see what the data will show after her changes have been in place for a longer period. If they aren’t working or there’s “an unintended consequence,” Rollins said she will adapt.

Rollins also wants to find other ways to change her office, saying she seeks out young, new staffers and tells them: “Explain to me how amazing your job is. And then also show me all the things that need to change.”


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