Meet the 2019 Bostonians of the Year: Andrew Lelling and Rachael Rollins - The Boston Globe (2024)

She surprised a lot of political hands, both for how decisive her win was last fall over better connected Democratic competitors, and for how explicit she was with voters about her plans to radically reshape criminal justice in Greater Boston. Another first-time district attorney might be inclined to protect the political capital that comes from winning 185,000 votes. (That’s approaching three times the tally Mayor Marty Walsh garnered in his last election.) Rollins sees things differently: Why leave a better paying, less punishing job if you aren’t going to spend your political capital on something meaningful, like a bold plan to make the county safer and the system fairer?

In March, she issued a 65-page memo ushering in a new progressive approach to law, order, and justice. Among its more controversial components, it lists 15 nonviolent offenses, from shoplifting to drug possession, where her office’s default position would be to not prosecute. Her memo drew “soft on crime” fire from a number of influential quarters, notably Governor Charlie Baker’s office, US Immigration and Customs Enforcement, and the business community.

On this November morning, she knows that shoplifting is what the merchants will want to talk about, so she sees no point in delay.

A tall, gray-haired man, who sells sheepskin-lined slippers from his pushcart, stands up. “If somebody comes in and takes your product and leaves without any fear of being prosecuted, what happens is gangs of shoplifters descend on you. And that’s already happening,” he tells Rollins. “How can we best be protected so that we’re not being victimized?”

There’s an unmistakable edge to the question — “without any fear of being prosecuted” — but Rollins doesn’t flinch. You can almost detect a hint of delight in her eyes, as if she relishes the chance to try to change a roomful of minds.

It’s the same look I’ll see later that night when a Bloomberg Radio host pointedly asks her, “Who made you the king?” and Rollins smiles, waits a beat, and replies, “First of all, it’s queen.”

And it’s the same look I’ll see a few days later when I sit with her and her white Irish father and black Barbadian mother as her parents lament the hypocrisy of “the liberals.” Despite being an interracial couple, longtime residents of the People’s Republic of Cambridge, and her parents, they are political conservatives and faithful Howie Carr listeners.

Rollins, a three-sport high school standout who attended the University of Massachusetts Amherst on a lacrosse scholarship, thrives in competitive situations, never more so than when it’s a competition of the mind.

Like a practiced trial lawyer guiding a jury, she walks the Faneuil Hall merchants through her thought process. How prosecutors’ traditional “answer to everything is jail,” so the court system is gummed up with cases for low-level offenses that usually end in dismissal, while too many homicides and other violent crimes go unsolved. How, in at least half of those nonviolent cases, the driving issue for the crime is mental health, substance abuse, food insecurity, or homelessness — problems far more effectively addressed, she says, with treatment and services than with the government footing the annual $55,000-per-inmate bill for a stay in county jail. And how, in a tradition that long predated her election, anyone convicted of petty shoplifting in Massachusetts would never see jail time until at least the third offense. “I’m just saying things out loud now,” she tells the crowd.

Rollins shows a willingness to educate — and be educated. Taking the merchants’ feedback seriously, she urges them to keep a written record of any shoplifters, since that paper trail will help her office distinguish the first-time offender trying to feed a drug addiction from the kind of repeat, reprobate professional thief described by the man selling sheepskin slippers. In the latter case, she says, “We’re going right to arraignment.”

MEANWHILE, IN A FEDERAL COURTHOUSE less than a mile away, another prosecutor — Andrew Lelling, US attorney for the district of Massachusetts — keeps tabs on the sentencing of the latest well-heeled defendant in the sprawling “Varsity Blues” college admissions scandal. On this same Wednesday in November, a real estate highflier gets six months in prison for having paid nearly half a million dollars to get his two kids into the University of Southern California as fake recruited athletes.

An international story involving vanity, fraud, greed, higher education, and Hollywood, Varsity Blues has kept Lelling in the headlines since news of the scandal broke in March. And that’s just one of the issues he’s been at the center of in 2019, a list that also includes immigration, public corruption, opioids, and marijuana. Everywhere you look, Lelling is there.

That Zelig-like quality is something he has in common with Rollins. It’s hard to think of a big local story in the last year where at least one of them didn’t figure prominently. On immigration, they have lined up on opposite sides. In other cases, such as in the kidnapping and death investigation of 23-year-old Jassy Correia, they have worked together.

The two hold very different profiles and philosophies for crime fighting. Rollins is an emerging leader in the national progressive prosecutor movement. Lelling is a law-and-order conservative and the only appointee of President Trump serving in Massachusetts — a self-described “red dot in a blue state.”

Like Rollins, Lelling has ample experience being around people with vastly different politics. He cracks that he grew up in “maybe the only [politically] conservative Jewish household in New York.” His wife, a juvenile court judge appointed by then-governor Deval Patrick, comes from a liberal family and her brother served as acting solicitor general in the Obama administration.

Lelling and Rollins previously worked together as assistant US attorneys and have kind, if slightly guarded, words for each other. Despite their ideological differences, they share a determination to make the judicial system fairer, insisting that those with wealth and status shouldn’t be treated differently from those with neither.

“I admire Rachael’s courage in innovating,” Lelling says. “Even though philosophically I disagree with the approach, given a year or two, one of two things is going to happen: She’s going to look like a genius, because crime drops, and her recalibrated approach worked out. Or it’s going to be a disaster.”

Rollins praises Lelling’s smarts and energy, but stresses that he can’t hope to make the kind of systemic change she is attempting. That’s because he is an employee serving at the pleasure of the president, not an elected official like she is. “If Andy published a 65-page memo” spelling out his own dramatic policy changes, she says, “he would be packing up his things the next day.”

Lelling says that in most of the areas where their work intersects — gangs, guns, opioid trafficking — he has found Rollins to be a strong partner committed to reducing violent crime. In the vast majority of street crime cases that her office handles, he says, there is no overlap at all.

Through Lelling and Rollins, residents of this region are getting to witness two deeply ambitious and largely parallel approaches to criminal justice. They are both aggressive, locked in, and uncommonly fearless. And as closely identified as Rollins is with the Democratic left and Lelling is with the Trumpian right, they have both demonstrated independence in challenging the excesses of their own ideological camps.

For being serious, thoughtful change agents more focused on improving results than scoring partisan points, they are our Bostonians of the Year.

ON A BEAUTIFUL AUTUMN DAY in 2018, Andy Lelling strolled Amherst College, a picturesque campus of handsome brick buildings garlanded by oaks and maples in their golden-to-scarlet glory. He thought to himself: This looks about as perfect as an elite New England liberal arts college can be.

He was visiting Amherst with his daughter, then a high school senior in Sharon. Like everyone else who had crowded with their kids into the information session, he knew the intense pressure so many kids feel to gain admission to highly selective colleges. Unlike everyone else in the room, though, he had firsthand knowledge of the outrageous lengths some parents would go to make sure that happened.

At the time, Lelling was about six months into the investigation that, in another six months, would spark a nationwide conversation about the madness of college admissions and sports — and make actor Lori Loughlin famous for something besides Full House.

“I live in a town where parents are obsessively focused on their children’s college prospects,” Lelling says now. “Millions of parents deal with this every year.” The difference with the parents his office charged is “they took the extra step of acting on those anxieties by knowingly participating in a fraud and bribery scheme.”

The experience prompted Lelling to double down on a message he had been giving his daughter: Please don’t freak out about this. Whether or not you get into an elite college, you’ll be fine.

He speaks from experience. He earned his bachelor’s degree from the State University of New York at Binghamton, and from there he went to an Ivy League law school, the University of Pennsylvania. As a first-year law student, he met his future wife, Dana Gershengorn, when they joined the same Friday night poker group. “Andy is not a good bluffer,” she says. “What you see is what you get.”

As their daughter was waiting to hear back from colleges this year, at the same time that the Varsity Blues investigation was intensifying, Gershengorn fretted, Please God, let her settle on a college before all of this breaks. She did, choosing Gershengorn’s alma mater, the University of Michigan. Not long after, Lelling and the FBI announced the sweeping Varsity Blues charges against 50 people around the country.

As for why they named this investigation after a forgettable 20-year-old movie starring James Van Der Beek, Lelling insists it wasn’t his decision. When the FBI announced the handle during their joint news conference, Lelling recalls, “I’m thinking, that is the dumbest name I’ve ever heard.” For weeks, he refused to use it, preferring “the college admissions case,” but eventually gave in.

During a recent talk at Lasell University, someone asks Lelling why the US attorney in Boston is overseeing a case where so much of the action took place in California. “Luck,” he quips. His office had been tipped off while investigating an unrelated case. “You wouldn’t believe how many US attorneys complained that I got to do the Varsity Blues case,” he says, adding with a mischievous smile, “We’re all super-ambitious publicity hounds!”

The 49-year-old with the bald dome and closely cropped beard admits he has a healthy ego. But his wife and their teenage daughter and son keep it in check, as do his very smart and very liberal in-laws. “The least impressed person in the world that I am the US attorney? My wife,” he says. “Second least impressed? My mother-in-law” — a retired Massachusetts Superior Court judge. “After 22 years of marriage,” his wife says, “Andy has yet to convince my parents of anything.”

Lelling grew up in New York’s Rockland County, the youngest of three sons born to a homemaker and a dentist who practiced in the Bronx. It wasn’t until high school when it dawned on him how much more politically conservative his family was than most others around him. He retains much of that conservative outlook, but says what he prizes most — and what he has tried to impart in his kids — is independent, rigorous thinking.

He’s a law-and-order guy with some Libertarian tendencies. He says he’s been a supporter of gay marriage “forever,” arguing “it’s not the government’s business who loves who, or who gets to get married.”

It’s a position shaped at least in part by family experience. When he was 10, he swiped the diary belonging to his middle brother, Marc, who had revealed in its pages that he was gay. It was nearly a decade before Marc came out to him and his parents.

He says the news was tough for their father to hear, but he ultimately accepted it out of pragmatism: He loved his son and this is who he was. Unfortunately, Lelling says, his brother’s life was filled with sadness. Marc was clinically depressed and HIV positive and took his own life in 2017.

In his first two years as US attorney, Lelling has shown that he shares his late father’s pragmatism. He knows that if he fails to “swim in the same direction” as Trump and US Attorney General William Barr, they will show him the door. He also knows, however, that he is not the US attorney in Alabama. “You constantly have to think about how what you are doing interacts with a very left-leaning populace,” he says.

He knows he has to push hard on immigration cases, but he holds considerable discretion on which ones to pursue, given limited resources. “You can prosecute the grandmother who returned illegally to see her grandkids or you can prosecute the guy who’s a drug dealer who was deported, came back into the United States, and continued drug dealing,” he says. “We do the second one.”

Lelling has earned a surprising level of bipartisan praise. A notable exception was the heavy criticism he drew last spring from some progressives for his prosecution of the Newton judge who allegedly helped an undocumented immigrant evade a federal agent. Lelling insists the case is not about immigration but about how no one is above the law, not even judges. “The law,” he says, “has to apply equally to everyone, regardless of status.”

Spending so much of his adult life around people with different views has sharpened his thinking. Occasionally, it prompts him to change his mind. Take affirmative action: Although he continues to oppose it in college admissions and the private sector, he’s come to appreciate its importance in positions of public authority, especially the prosecutors, judges, and police who have enormous power to send people away. As he puts it, “There are certain walks of life where the public needs to see that it’s not all white guys.”

In 2001, when he went to Washington to work for the George W. Bush administration in the Justice Department’s Civil Rights Division, he was surrounded by fellow conservatives for the first time in his life. “It was disorienting,” he says. He prefers being around a diversity of viewpoints, to guard against groupthink.

So much of his job boils down to judgment calls, looking for the “moral oomph” when deciding whether to prosecute a case. In this day of heightened polarization, Lelling says, “There’s so much more intense moral indignation on both sides. I’m in the middle. I decide where the line is.”

ON A SUNNY, BRISK FALL Saturday, Rachael Rollins, a red hoodie covering her head, weaves her way through the stands of the soccer field at Buckingham Browne & Nichols School in Cambridge. She spots her ex-husband, and gives him a hug. They’re here to cheer on their 15-year-old daughter, Peyton. Also on hand are Rollins’ parents, two sisters, and several nieces and nephews.

Peyton’s first love is track and field — she is considered one of the very best hurdlers for her age in the country. “Let’s go, Pey!,” Rollins, a BB&N alum, yells when her daughter takes the field for this playoff soccer game. But she cheers even louder for a teammate whose aggressive play has earned her multiple yellow cards and a reputation for staying on the field through bloody noses. “That,” Rollins whispers to me, “is how I played.”

It’s something else being in the bleachers at a rarefied private school like BB&N. Several teenagers bump into me while trying to get by, and not a single one fails to apologize. After one referee’s controversial call, a parent shows his fury with a huff of “Absurd!”

Rollins, whose framed All-Scholastic plaque remains on display in the athletic center, is grateful for the first-rate education she received at BB&N. She also appreciates how her time there opened her eyes to the incredible amount of privilege some people in the world enjoy — and how invisible it can often be to them.

When Rollins talks about fairness, she is informed by the very different worlds she has floated between in her life. She’s seen how a wealthy, well-connected person who makes a stupid decision can bat it away like a mosquito. And how a poor or desperate person who makes a stupid decision can be thrust into a downward spiral. Also, the people without connections or resources who get caught up in our current system are disproportionately brown or black.

After BB&N’s win over Thayer Academy, I sit with Rollins and her parents, Esther and John Splaine. It’s a complicated but intensely close clan. Her sister Bekah Salwasser, a graduate of Brown University and former professional soccer player, is now the executive director of the Red Sox Foundation. Her two brothers have both battled addiction and gone through the criminal justice system. Rollins is the legal guardian for the daughter of one of her brothers, as well as for the daughter of her youngest sister, who struggled with addiction but is now clean and working to regain full custody.

In 2016, when Rollins had to undergo a double mastectomy, she initially refused to take the painkillers that her doctor prescribed. “Three of my four siblings danced with the devil and lost,” she says.

Watching her brothers go through the justice system made her intimately aware of how often it can be counterproductive and dehumanizing. Her parents don’t disagree, but offer a personal accountability argument: If you don’t do anything wrong, you usually don’t end up anywhere near the system. Rollins stresses that true accountability means a system that holds everyone to the same standard. They all agree we’re a long way from that.

Her parents try to serve as a tuning fork for their oldest daughter as she works out her policy positions. When she came up with the 15 offenses her office would typically not prosecute, they encouraged her to stress that there would still be consequences, just alternative ones. The point is to make changes that help a chronically inefficient system work better.

Rollins likes to rib her father about his skills as a political prognosticator. On her phone, she retrieves the e-mail he sent her in February 2018, when she told him she planned to run for Suffolk County DA. She had an impressive pedigree — law degrees from Northeastern and Georgetown, and good jobs in the private and public sectors, including as chief legal counsel at the Massachusetts Port Authority. However, she lived in Medford, which is in Middlesex County, and her residency issue was one of several detailed reasons her father cited in strongly advising her not to run. She wrote back: “Thanks for your honesty, Dad. I plan on printing and framing this email. It will be the first thing I hang up in my office as the Suffolk County DA. Love you, Rachael.” (“Let’s do this,” her dad replied, and quickly became a tireless campaign volunteer.)

Rollins now rents out her Medford house and lives with her daughter and nieces in a rented town house in Roxbury. She continues to open up her home to children in need of emergency placement in the foster system, having hosted nearly 50 kids over the years.

Because of her upbringing, she jokes, she is fluent in “white Irish male.” It remains the lingua franca of Boston law enforcement, so her fluency comes in handy. During one of her staff meetings that I sit in on, there are so many references to Sully, Danny, Bobby, Billy, and Murph that it feels as if I’ve stumbled into a reunion for BC High’s class of 1979.

Rollins also sent a powerful message with her most important hire: choosing Dan Mulhern to be her first assistant and chief deputy (naturally, she calls him Danny). A Boston native, he seems to know just about every Irish cop and court officer in the city, having previously served as the head of the DA’s gang unit and as Mayor Walsh’s top public safety adviser. But, like Rollins, Mulhern is a thoughtful reformer who has important lived experience — he lost a brother who was struggling in recovery and lost another relative to homicide.

Because of the circles he travels in, Mulhern hears lots of complaints from cops who see Rollins as some kind of soft-on-crime ideologue. He tries to set them straight, but he says he wishes more of them could see how hard she works, how much she cares, and how committed she is to getting this right in the end.

There’s a practical side to her that few of her critics appreciate. Many progressive politicians say ICE should be abolished, and there’s a whole national movement calling for the abolition of prisons. Rollins supports neither. She wants reform, not abolition — a fairer system that doesn’t criminalize being poor, or black or brown, or having addiction or mental health issues. Still, she says, there are murderers, rapists, and kidnappers who need to be removed from the community. It won’t work to send those dangerous criminals to a restorative justice circle.

Rollins is intense and real. Almost everywhere she goes, she carries a spreadsheet that lists the homicides that have happened on her watch — the number is now up to 42. During weekly meetings with her unit chiefs, she presses for updates on each unsolved murder. In addition, she has begun the process of having her office review nearly 1,400 unsolved homicides going back to the 1960s.

The thing about crime is everything is connected. If the system fails victims, they are more likely to end up as perpetrators. “If we fail them in juvie, we see them in gangs,” she says. “If we fail them in gangs, we see them in homicide.”

As Rollins approaches her first anniversary in the job, she remains restless as a reformer in ways big and small. Earlier in the fall, she was summoned to jury duty. She showed up, waiting with all the other citizens. Her mind was racing. Instead of having people sitting around, frustrated by the inefficiency of the court system, she wondered: How could we put all this talent to good use? “If this was Denmark,” she says, “we’d have everybody out cleaning a park.”

FOR ALL THEIR DIFFERENCES, Rollins and Lelling have much in common. They are both funny and blunt, about the same age, and oversee similar size staffs and $21 million budgets. They both welcome being challenged by people who see the world differently. And they are both passionate about increasing fairness in the justice system, albeit with very different approaches.

Depending on your politics, you probably view one of them as being far more deserving of praise than the other. But consider this thought experiment: If you lean left, imagine a US attorney in Boston who would treat Massachusetts as if it were Alabama, rounding up people buying weed from a licensed dispensary and undocumented immigrants who have illegally crossed the border once to reunite with family. If you lean right, imagine a Suffolk County DA who would call for the abolishment of ICE and prisons.

If you’re inclined to fault Lelling or Rollins for being too extreme, look closer. You might actually like the restraint you see.

Neil Swidey is the Globe Magazine's staff writer. E-mail him at neil.swidey@globe.com or follow him on Twitter @neilswidey.