DISTRICT ATTORNEYS and sheriffs are traditional “law and order” positions, inhabited by officials often viewed as tough on crime. These jobs are elected, but incumbents, particularly DAs, have often sailed easily to reelection – and sometimes chosen their successors – with little public attention. That has changed in recent years, as a growing number of liberal-leaning reformers have run for these positions, and progressive groups have begun organizing around them, as a way of changing the criminal justice system from the inside. That is evident in the current election cycle, where several reformer candidates are running, generating growing public interest.  

But this fall’s elections will also face a test of whether voters are actually interested in that ethos.  

Berkshire County DA Andrea Harrington, a reformer elected in 2018, is up for reelection and facing a Democratic primary challenge from Timothy Shugrue, who has criticized her for being too soft on crime. Shugrue has charged that Harrington’s policies led to an increase in gun violence, and said he disagrees with Harrington’s “soft stances” on crimes like drug possession, larceny, and breaking and entering. Shugrue  has touted support from local law enforcement organizations, and the Berkshire Eagle endorsed him, charging Harrington in sharp terms with mismanaging the office. 

In Suffolk County, both Democratic DA candidates, Ricardo Arroyo and Kevin Hayden, say they support liberal-leaning policies, though Arroyo is widely viewed as more progressive. Policy differences in that race have been overshadowed by sexual assault allegations against Arroyo. But there are real differences –Hayden would keep a gang database; Arroyo would dismantle it. Hayden backed away from a commitment made by his predecessor, Rachael Rollins, not to prosecute low-level offenses; Arroyo supports the policy. 

The American Civil Liberties Union, a liberal-leaning organization that does not endorse candidates, has been a leader in the recent education efforts. In 2018, the ACLU of Massachusetts ran an education campaign about district attorney’s races. That year two reform-minded district attorneys were elected –Rollins and Harrington. ACLU officials believe their campaign helped boost turnout in the races. This year, the ACLU expanded its voter education campaign to sheriff’s races, publicly posting candidate questionnaires and hosting candidate forums. 

An ACLU poll found that only 17 percent of Massachusetts voters can correctly identify their county sheriff. For the most part voters don’t know what sheriffs do, but they have power to make a difference in the lives of people,” said Carol Rose, executive director of the ACLU of Massachusetts. “We believe if voters understood the roles and responsibilities of sheriffs, they would be more likely to vote and more likely to ask questions of the people who are running for sheriff and make sure people who are elected sheriff are accountable to the voters.” 

In addition to Harrington and Arroyo, several races this year feature reform-minded candidates seeking criminal justice roles. In Plymouth County, Democrat Rahsaan Hall, a former ACLU civil rights attorney who helped lead the organization’s 2018 DA education campaign, is running against incumbent Republican Timothy Cruz. Former prosecutor Shannon McMahon is giving Bristol County District Attorney Thomas Quinn his first challenge in seven years in the Democratic primary, in a race WBUR described as a progressive criminal defense attorney taking on a moderate DA.  

In Essex County, clinical social worker Virginia Leigh is running in the Democratic primary for sheriff against incumbent Kevin Coppinger. Three Democrats are in a tight primary race in Bristol County, where the winner will try to defeat Republican Sheriff Tom Hodgson.  

After police violence against Black men inspired the Black Lives Matter movement, Hall said the public saw the police as the source of injustice in the criminal legal system. But criminal justice reform advocates tried to direct attention to “the people who have some of the most power in the system.” 

Prosecutors oversee decisions, including what crimes are charged and what sentencing recommendations come before the court. Sheriffs oversee conditions, programming, and treatment in jails.  

“I think part of the reason there is an increased focus on prosecutor and sheriff races is because more people have a better understanding of how powerful these positions are,” Hall said. 

Hall, a former Suffolk assistant district attorney, said heading the ACLU’s 2018 education campaign was one factor that led him to run for the job. “Seeing the lights turn on in people’s minds when I told them about what it is DAs have the power to do and how those decisions could dramatically impact racial disparities, overincarceration, outcomes for people who are struggling with substance use disorder and mental health issues, it really solidified the idea that someone in this position could make a meaningful difference,” Hall said.  

Essex County Sheriff candidate Virginia Leigh talks to supporters. (campaign website)

Leigh, the Essex County social worker, has worked in community health centers in Lynn and Brockton, and in a Mexican detention center. She decided to run for sheriff after participating in a Democratic women’s training program run by Emerge Massachusetts last year. She argues that the role of sheriff is not one of law enforcement but of human services work. The county jail, she said, “happens to be our largest provider of mental health and substance use treatment, which also happens to be our most important center for rehabilitation.”  

She decided to run against Coppinger, calling him a reluctant reformer, citing in part his early hesitation in providing medication assisted treatment for substance use disorders in jail. (The Telegram & Gazette reported that Coppinger now touts addiction-related reforms.)  

Yet while Leigh compares herself to another social worker and reformer who served as a long-time sheriff – former Hampden County sheriff Mike Ashe – Ashe actually endorsed Coppinger. 

Martha Durkee-Neuman works for Mass Alliance, a progressive advocacy coalition, and is an organizer with the Justice for Massachusetts Coalition, a coalition of labor unions and liberal organizing groups who support candidates “that support decriminalization, anti-mass incarceration, and transparent justice.”  

The group endorsed Arroyo and Hall for district attorney, and Leigh and Bristol County candidate Paul Heroux for sheriff. Durkee-Neuman said the coalition came together for the first time in 2018 to focus on the Suffolk County district attorney’s race and ensure that progressives threw their weight behind a single candidate – Rollins – rather than splitting the vote. This is the first election cycle they have endorsed multiple candidates for sheriff and DA.  

“District attorneys and sheriffs have a lot of power to reshape our criminal legal system,” Durkee-Neuman said. “A lot of members of the coalition are folks that come from communities directly impacted by the criminal legal system, and we care a lot about electing progressives that can make system changes in both those offices.” 

Jonathan Cohn, policy director at Progressive Massachusetts, said similarly that his organization first got involved in a district attorney race in 2018, to back Rollins. This time, Progressive Massachusetts endorsed Arroyo and Hall and joined the Justice for Massachusetts Coalition. Cohn said the DA plays a role in expanding or curtailing mass incarceration and the sheriff is also a major actor, but “They’re positions that often go somewhat under the radar.”  

Nonprofit organizations that are barred by tax law from endorsing candidates have also become more active. Brockton Interfaith Community never got involved in a district attorney’s race until this year, when it is running an education campaign about Hall, Cruz, and the DA’s role. 

“The DA makes a lot of decisions about whether or not people go to prison and how long they go for, and there’s a lot of evidence that there’s lots of people locked up in our prisons that are coming from Brockton right now that literally didn’t have to be there,” said William Dickerson, executive director of Brockton Interfaith Community. “We as an organization decided this was an important moment to educate the community about what a DA does and the impact it has on communities.” 

Dickerson charged that the district attorney’s office has been “a place historically where racism sits and white supremacy sits,” particularly in sentencing decisions. He said he wants to ask the candidates where they stand on issues around racism and bias. Hall is Black; Cruz is white. 

Andrea Sheppard Lomba, executive director of United Interfaith Action of Southeastern Massachusetts, said the organization has become more active than ever in voter registration and education tied to increasing taxes on income over $1 million, retaining a law giving driver’s licenses to immigrants without legal status, and voting in the Bristol County sheriff’s race.  

The nonprofit organization does not endorse. But Lomba said the focus on the sheriff’s race is because the last time most sheriffs were up for reelection, in 2016, more than 600,000 Massachusetts residents left the race blank. “That’s a very powerful statement about people not being aware of the role and the power of this position, and the impact it makes in the community in terms of overseeing the jail system, and the health and wellbeing of those who are incarcerated,” Lomba said.  

Marlene Pollock, co-founder of the Coalition for Social Justice, which works in New Bedford, Fall River, and Brockton, said her organization endorsed Hall for Plymouth district attorney and has been actively campaigning for Paul Heroux for Bristol County sheriff. In Bristol County, the incumbent Hodgson is an outspoken Donald Trump supporter who has been criticized for years for alleged mistreatment of inmates. The coalition endorsed Heroux, a former state representative, as the strongest Democrat to beat Hodgson. Pollock said the deciding moment for her group was when Hodgson said in 2017 that he wanted to send incarcerated people to the US-Mexico border to help build a border wall. “That really galvanized a lot of people to say what’s going on here?” she said.