Get Informed

Subscribe to our newsletters for regular updates, analysis and context straight to your email.

Close Newsletter Signup

A Massachusetts District Attorney Tries To Crown His Successor

In the Berkshire County DA race, the establishment is resorting to extreme measures to ensure it maintains power and avoids change.

Departing Berkshire DA Doug Capeless and his interim successor, Paul Caccaviello
Berkshire County District Attorney

A Massachusetts District Attorney Tries To Crown His Successor

In the Berkshire County DA race, the establishment is resorting to extreme measures to ensure it maintains power and avoids change.


Berkshire County, the sparsely populated Massachusetts region abutting New York, should be gearing up for an unusual event in the fall: an open race for the district attorney’s seat. But the departing DA short-circuited that electoral process and anointed his successor through backdoor channels. Emails obtained by The Appeal reveal how the old guard has tried to hold on to power and beat back reformers’ challenge.

On March 1, Berkshire District Attorney David Capeless stepped down after 14 years in office. The resignation was apparently a strategic move to ease the path to election for his hand-picked successor, First Assistant District Attorney Paul Caccaviello, with the help of Governor Charlie Baker.
“I’m taking this step now,” Capeless told reporters at his resignation press conference, “because I want Paul to be able to run as the district attorney, as I did 14 years ago…. I want to thank Governor Baker and Lt. Governor [Karyn] Polito for their careful consideration and confidence that Paul is the right person for the job.”

Running as an incumbent is a huge advantage, said Drew Herzig, an organizer with Indivisible Pittsfield, a local progressive group. Incumbency affords candidates the weight of the office and allows them to draw on existing donor and influence networks — no small feat in the Berkshires, where candidates don’t need a lot of money to be competitive and where reputation and connections can be key to influencing voters.

Emails between Capeless and Baker’s office, reviewed by The Appeal and included below, tell a story of what numerous criminal justice professionals and observers described as an unprecedented level of cooperation between the DA’s office and the Baker administration to handpick the DA.

The handoff appears to have received the governor’s blessing after a meeting on Feb. 7, the emails show. Baker’s chief legal counsel, Lon Povich, coordinated meetings for Capeless and Caccaviello with both Baker and Polito. Capeless sent the governor’s office a timeline for his resignation and Caccaviello’s appointment, the emails show, but Povich was unable to endorse Capeless’s proposed sequence of events until the February meeting.

Capeless told Povich he intentionally took out re-election papers before his March 1 announcement to confuse  local media.

“Still on track,” Capeless reassured Povich of the handoff to Caccaviello, “just stalling.”

Later, Povich provided feedback on Capeless’s resignation letter.

“Glad this is working out,” he wrote.

Capeless said repeatedly in emails to Povich that he was delighted that the transfer of power would ensure Caccaviello had a leg up on the competition in the Democratic primary. To that end, the departing DA presented Povich a proposed timeline that would allow the governor to appoint Caccaviello and give the new DA “ample time to form a campaign committee and gather the necessary signatures to get on the ballot.”

In a brief phone interview, Capeless said that because this was the first time he had resigned from a position, he couldn’t speak to how normal the process was. The former DA said Povich’s edits to Capeless’s resignation letter and the governor’s involvement with Capeless’s resignation timeline was “not unusual” and that he would not discuss the February private meeting.

Caccaviello was unavailable for comment for this article.



A Democrat, Caccaviello will face two progressive challengers in the primary on Sept. 4:  local defense attorneys Andrea Harrington and Judith Knight. Harrington, who was the first to publicly announce her candidacy, entered the race with an existing political machine that was ready to go after an unsuccessful state Senate bid in 2016. She told The Appeal she plans to pursue a different approach to criminal justice.

“This is a really important race for the future of Berkshire County,” Harrington said. “It’s an opportunity to move into the future with a DA using evidence-based programs that address the root causes of why people get involved in the criminal justice system.”

Restorative justice, an approach to crime that seeks to rehabilitate and repair harm rather than punish, is gaining in popularity in the country. Harrington hopes to pursue these ideals in her DA office, she said. She wants to create a citizens’ advisory board to hold her office accountable and to get input from the community for what crimes to prioritize. As DA, Harrington said, she would work to ensure not only that people who have been in and out of the criminal justice system have a chance to rehabilitate themselves without facing unfair incarceration, but also that people just entering the system have the opportunity to keep their mistakes off their permanent record.

While it’s an idea of criminal justice that might have been out of place in decades past — especially after the “tough on crime” legislation of the Reagan era — today Americans are more amenable to restorative justice and alternatives to punitive incarceration.

“The conversation over crime has been fear-based; to be a DA, you must run on being ‘tough on crime,'” said Harrington. “Now, I think because of the opioid crisis, the conversation has opened up and all people are seeing what communities of color have known for a long time: The system doesn’t work.”

It’s a theme that has become more prevalent as liberal candidates join the criminal justice system—most famously in the last year with the election of District Attorney Larry Krasner in Philadelphia.

“I was very inspired by Krasner,” Harrington said. “I look forward to working on specific policies like ending mandatory minimums, limiting fines and fees for the indigent, ending overcharging for nonviolent offenses, and diversion programs that shift resources from incarceration to programs that address underlying causes leading to criminal conduct.”

Along with the already established Berkshire County Drug Court, Harrington wants to pour resources into diversionary programs for established and new offenders. To do that, the DA’s office under Harrington would choose not to prosecute certain crimes if the defendants seek treatment and therapy.

The prospect of change, Harrington believes, scares the DA’s office. Capeless’s office has long had a reputation in the commonwealth for being particularly draconian and harsh. Locally, the former DA is known for his zealous pursuit of drug crimes: In one instance, he tried repeatedly to use school zone charges against one teenager over a decade ago. Capeless has also railed against marijuana legalization and opposed the creation of an alternative drug court.

Harrington sees the power transfer between Capeless and Caccaviello as evidence that the office is afraid of a real debate on the issue of criminal justice and fears being held accountable by the public.

“The fact that they will go to these lengths to avoid a contested election where the community is looking to have these important conversations on criminal justice just says they are afraid of that conversation,” said Harrington. “And I think they have good reason to be afraid.”

Rahsann Hall, director of the American Civil Liberties Union of Massachusetts’ Racial Justice Program, said the handoff is especially “disturbing” because of its impact on the democratic process. The power transfer in the Berkshires adds to the public’s misconceptions about the office, he added. In fact, an ACLU of Massachusetts poll found that 38 percent of state residents don’t even know DAs are elected.

Massachusetts has one of the lowest incarceration rates in the nation, Hall said. But that disguises an ugly truth: The commonwealth has one of the highest racial disparities in incarcerated people and a high rate of recidivism.

“This suggests that the system, as it functions now, does not work,” said Hall, “at least not in a way that promotes healthy and happy communities.”

With all the discussion around mass incarceration and the recent passage of criminal justice reform in Massachusetts, Hall said, choosing the right DA is more important than ever—though he made clear that he was not endorsing any candidate either personally or officially.

“The most significant player in the criminal justice system that has most power is the DA,” Hall said.

DAs have control over prosecution decisions, said Harrington, and that should lead to more fair and just outcomes. But Caccaviello’s office and the office of his predecessor haven’t taken advantage of that discretion. Rather, the policy of the office is that their role is solely to enforce the law, and that’s a position that Harrington disagrees with vehemently.

“The reason we have an elected DA is because the DA is supposed to be the conscience of the community,” she said. “The fact that we have a DA that doesn’t understand that should trouble people.”