As Anti-Reform Prosecutors Depart, Will Massachusetts Really Change?

January 11, 2022

The landscape of the criminal-legal system in one of the nation’s most progressive states is changing.

Two of 11 elected district attorneys in Massachusetts—DA Jonathan Blodgett of Essex County, with a population over 800,000, as well as Cape and Islands DA Michael O’Keefe—have opted to not run for re-election in November this year.

Both men have fought even mild decarceration efforts in the legislature.

A third conservative top prosecutor, Plymouth County DA Timothy Cruz, whose jurisdiction has over half a million residents, has said he will be running in 2022. But he may face the fight of his political life if he comes up against Rahsaan Hall, who led ACLU Massachusetts’ public education campaign about the power of prosecutors. Despite mounting rumors, Hall has not yet fully committed to the race.

But the most immediate change—and one that could point in the opposite direction—is coming in Boston. Former Suffolk County DA Rachael Rollins has just been sworn in as US attorney, the state’s top federal prosecutor. While President Biden’s choice of Rollins might spell a less carceral approach to more serious crimes, the nature of her new role will remove her capacity to drop whole categories of lesser charges.

As DA, Rollins received progressive accolades for her campaign promise to default to non-prosecution for 14 low-level misdemeanors. She made progress in this regard, though critics pointed out that she still prosecuted these cases on occasion.

Governor Charlie Baker, a Republican, appointed Kevin Hayden as Rollins’ replacement on the local level. Rollins then stated in a press release that “Governor Baker took great care to choose an individual with subject matter expertise, leadership experience and a respect for and fluency in the different concerns and needs of each of the neighborhoods that make up Suffolk County.”

However, there is no confirmation that Hayden, who would enjoy an incumbency advantage if he decided to fight the November 2022 election, plans to continue the data-backed declination policies that made Rollins a national figure. And there are reasons to be skeptical that Hayden is cut from the same cloth as Rollins, beyond the fact that Gov. Baker picked him.

In the 1990s, Shannon Booker was one of eight women profiled in a film about domestic violence survivors killing their abusers. She became a prominent domestic violence advocate after her release on parole. However, several years later, her mental health worsened, and under the control of a new abusive partner, she stole a tourist’s wallet. It was Hayden who aggressively pursued a conviction for the theft. The judge acquitted her anyway.

It is still unclear whether Massachusetts’ changing of the prosecutorial guard will result in a significant change of direction for the state.

In 2001, Hayden joined former Suffolk County DA Dan Conley’s Gang Unit, where he spent several years. Hayden’s experience there was similar to Greg Henning, whose unsuccessful 2018 election bid to become Suffolk County DA saw him tagged as the “law-and-order” candidate that year. Both men complemented day jobs as hard-nosed gang prosecutors with community service in neighborhoods of color heavily impacted by crime and violence.

At least in the case of Henning, the people who lived in these neighborhoods saw through the optics. Prior to serving as the head of Innovation & Strategy for DAl Rollins, Bobby Constantino mapped out campaign contributions to the five Democratic contenders in the 2018 DA race. He found that Henning received the fewest contributions from residents of two of Boston’s most heavily prosecuted areas. Rollins received the most.

Taken altogether, it is still unclear whether Massachusetts’ changing of the prosecutorial guard will result in a significant change of direction for the state.

While Blodgett and O’Keefe are retiring—removing the prospect of anti-reform incumbents seeking re-election in Essex County or Cape and Islands—no reform-minded candidates for these jurisdictions have yet surfaced. And these districts are not bastions of the Democratic Party’s left flank like Boston is.

Similarly in Plymouth County, where Rahsaan Hall may run as a full-on reformer, Trump received 40 percent of the vote in 2020.

Meanwhile Hayden has not yet submitted nomination papers for a re-election bid, though he has until May 5 to do so. No reform candidates have surfaced in Boston to date.

Thus, the changing landscape is no guarantee. But if strong reform candidates emerge in time, it could still be an opportunity.


Photograph by tableatny via Flickr/Creative Commons 2.0

Rory Fleming

Rory is the founding attorney of Fleming Law LLC, an immigration law boutique in Philadelphia. He has worked for a variety of criminal justice and harm reduction nonprofits, including Law Enforcement Action Partnership and Harvard Law School's Fair Punishment Project, and provided campaign services for over a dozen district attorney campaigns. His articles have appeared in the Atlantic, Slate and many other outlets.

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