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The Twists and Turns of the District Attorney's Race
By Andy McKeever, iBerkshires Staff
03:59AM / Wednesday, November 07, 2018
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The first debate among Andrea Harrington, Judith Knight, and Paul Caccaviello was just the start of a long election season.


Andrea Harrington and her family the night of the primary.
PITTSFIELD, Mass. — It was Thursday, March 1, 2018, when the body of a woman was found in a nearby wooded area. Hours later, District Attorney David Capeless sent a notice to media outlets that he had a "major announcement."
 
Television stations on the scene where the body was found quickly went to air telling the public that a major announcement was pending.
 
The media advisory didn't say much but given the timing, it was assumed by many that Capeless would release information regarding the homicide and many in the public were glued to social media waiting to see if it was the body of a woman who had been missing.
 
Capeless took to the microphone in front of numerous media outlets.
 
"I am proud of what I have accomplished in my career, and I leave with my head held high, though my shoulders may have sagged a bit. I am proud of the unity and cooperative efforts of law enforcement in Berkshire County which I have fostered and led since taking office,"  Capeless said as he announced his retirement.
 
The very local media felt this was a huge story. The district attorney who had easily retained his post as top prosecutor election after election was stepping down after 14 years. 
 
The out-of-town media, however, felt misled. The comments on live video of the conference posted repeatedly bashed Capeless, calling it opportunistic to announce his retirement when everyone was waiting for news. But he had already planned to announce his retirement, it just so happened that a body was found that morning.
 
Many of the stories written that day weren't so much about Capeless and his accomplishments, failures and successes, and the future of the district attorney's office. Instead, the focus became on how "awkward" the conference was.
 
And that is how it all began. The awkwardness never quite lifted.
 
It ended on Tuesday, Nov. 6, 2018, when voters of Berkshire County tossed out the old guard in a historic election that shall not soon be forgotten.
 
When Capeless stepped down leaving a void in one of the most powerful positions in local government, he did so early to give his first assistant Paul Caccaviello the benefit of running as an incumbent.
 
"I have great respect for Paul's character and abilities, and he has the experience and trust of our colleagues in law enforcement to give me the confidence that the Berkshire District Attorney's Office's legacy of fair and even-handed justice will continue under his watch," Capeless said when he was up front and truthful that he took the step early to give Caccaviello the power of incumbency.
 
Gov. Charlie Baker had agreed to appoint Caccaviello to take over the office before Capeless announced his retirement. 
 
"I will continue to look back and draw on my experience and the lessons learned in these 28 years to lead this office to know and recognize the difference between a hardened criminal, the sinner, the evildoer, or simply a wrongdoing. Those are distinctions not easily defined perhaps but years of experience make them more recognizable and needs to be treated accordingly," Caccaviello said on March 15 when he assumed the office.
 
Caccaviello was elated. He had worked up way up the ladder from being an intern 30 years earlier to now being the boss.
 
"Be assured that the good work of this office will continue today and beyond with collaboration, integrity, and professionalism will continue to be hallmarks of this office on all fronts -- holding the guilty accountable, being the voice of the victims," he said.
 
Between the announcement and Caccaviello's swearing-in, Commonwealth Magazine was at work. It was filing public records requests and on March 17, it released a report showing that Capeless hadn't just resigned early, but had worked for months with the governor's office to get Caccaviello in place. Capeless had even taken the step to take out nomination papers to throw reporters off the scent.
 
"FYI – There have been repeated inquiries by local media about why I hadn't pulled nomination papers, so I did that today, but immediately after that filed my retirement application. Still on track, just stalling until 3/1," reads an email from Capeless that Commonwealth Magazine had obtained.
 
The appearance of collusion didn't sit well with Andrea Harrington. 
 
"The powers that be have sort of our bestowed our next district attorney on us and I think that the people of Berkshire County really deserve more," Harrington said on "The John Krol Show" on March 16, the day before Commonwealth Magazine's report detailing the transition was released. "They deserve to be able to make the choice about who their elected leaders are going to be."
 
The Richmond attorney, fairly fresh off a failed run for the state Senate, entered the race.
 
"They tried to keep me out of this race. They tried to go as late as possible so I couldn't get my signatures," Harrington said in May at her campaign kickoff event. "But you know what, we had 50 volunteers from across the county and we got 1,500 certified signatures. On Sept. 4, they are going to really know that they are accountable for this community."
 
More frustration grew when uniformed police stood with Caccaviello during his campaign announcement, a potential violation of state ethics laws. A local resident filed a complaint with the state over it but the state still hasn't issued a public decision on the complaint.
 
Great Barrington attorney Judith Knight had run for the seat in 2006 with a progressive platform that wasn't well received at the time. But since then many of those ideas had taken hold. In late 2017, Knight was preparing to challenge Capeless again for the seat but the retirement caught her off guard. She paused to reconsider.
 
"I was going to run against David. He anointed Paul, which I disagree with, but Paul is not David. I wanted to know if Paul was open to change and I didn't see that. He promised continuity of the same. So I thought I had to go for it," Knight said in July, becoming the last to enter the race.
 
The stage was set as all three Democrats were seeking nomination for the county's top law enforcement job. 
 
Knight and Harrington shared similar views. They both were pushing for diversion programs, both pushing for affordable bails, both calling for the use of more drug courts, both calling for more transparency, and both saying the district attorney's office had been only focused on getting convictions for years and hadn't taken preventative measures.
 
"That's usually a low-level dealer striving to keep his or her habit going. They don't need jail time the first time. I would not enforce mandatory minimum sentences on these things. I think the judges are well equipped to make the right decision. Mandatory minimums are going out of style. It was a failed experience in the '80s," Knight said. 
 
Harrington said, "Community outreach is not just showing up and doing a lecture here and there. It is really part of engaging with the community in a meaningful way. One of the ways I'd like to do that is by starting a citizens advisory board. It would be a respected cross-section of members of the community that is weighing in on the work of the district attorney's office and how the DA can reflect the values of the community."
 
There were some differences between the two but for the most part, they staked out their positions as progressive candidates. 
 
Caccaviello, meanwhile, maintained that such changes are required under the state's recently passed criminal justice reform bill and he vowed to implement them. He said other concepts put forth by the two were already being done -- though often unknown because Capeless' office hadn't put much of an emphasis on sharing it with the public. 

Former District Attorney David Capeless resigned from the seat early to allow Caccaviello to run as an incumbent. But that move frustrated a large group of Democrats, including Harrington.

"I'm a supporter of them. If somebody comes in and they are afflicted with an addiction, which I consider is a disease and as a disease needs to be treated, the diversion programs give us that opportunity," Caccaviello said.

"If there is a mental health component, diversion programs will give us an opportunity to deal with that. There are also provisions for veterans."

His opponents said such changes could have already been done but there was no taste for it.
 
But above all, Caccaviello focused on his 30 years working in the office.
 
"My philosophy is to show compassion when it is appropriate, have a consequence when it is needed. And it is not mutually independent concepts. Many times, if not the majority of times, you have to have a balance when confronted with something. I've been in the office, been under different administrations, and I've handled over 5,000 cases. Every case is really a teachable moment and that is what informs my experience and that philosophy," Caccaviello said in July.
 
Meanwhile, the district attorney's race became the hot topic featured frequently on "The John Krol Show," as the city councilor took umbrage at the way Capeless handed the position to Caccaviello. Krol felt Caccaviello should have stepped away from the office to run and accused "the good old boys" of strong-arming their way into the office.
 
"I don't appreciate having my husband called a liar, having him be accused of circumventing the democratic process, while at the same time playing videos where he explains exactly what he is doing in an open and honest way. You guys are sponsoring this show and I want to let you know that I really don't appreciate it and neither do the Caccaviellos," is what Allen Harris of Berkshire Money Management heard on his voicemail in July.
 
It was a message from Betsy Capeless. Infighting among politicians isn't something new, but now the frustration of the way Krol continually talked about the transition boiled into threats to the livelihood of private citizens. 
 
"I have a big Italian family. I told them all. We are loyal. I liked your restaurant but I will never be back. Watch what you say word of mouth is key. Politics has nothing to do with it. It's human decency. The Highland is all I'm saying," reads a Facebook message from Karen Caccaviello to Luke Marion, the owner of the popular eatery Otto's and one who had sharply criticized the transition on his personal Facebook page.
 
It became known as "wifegate." The district attorney's wives had let their frustration out. It was a mistake and Caccaviello knew it.
 
"I am aware of it. I wasn't part of it. But for me, my wife's support of me and her defense of her family comes from a place of love," Caccaviello said. "When politics and social media intersect, it is tough. It is very tough. Honestly, lesson learned."
 
Another round of sharp criticism went Caccaviello's way. Meanwhile, there was another controversy brewing -- vote splitting. 
 
Those in the progressive camp were worried that Knight and Harrington would split votes and allow Caccaviello to easily claim victory. State Rep. Tricia Farley-Bouvier would suggest the two sides call a truce and team up but that received no traction.
 
Debates came fast and furious throughout the county. Harrington positioned herself as a reformer with progressive ideas to transform the county. Knight did, too, and targeted Harrington's lack of experience as limiting her ability to make it happen while attacking Caccaviello for policies and actions under Capeless. Caccaviello tried to straddle both fronts by supporting progressive change and emphasizing his experience.
 
"When he started this campaign four months ago, he was talking about continuity and continuing the work that has been going on in the DA's office and now after sitting on a debate stage listening to myself and attorney Knight, he's now come to Jesus and confirmed racial bias in the criminal justice," Harrington said, a roundhouse kick to Caccaviello's campaign at a forum in Williamstown.
 
Right then may have been somewhat of a "come to Jesus" moment for Caccaviello. By mid-summer, it was clear he was getting left behind in the debates and the emphasis on the progressive ideas. Voters weren't going to vote for him for progressive change. But they might because he has done the work.
 
"I am the only professional prosecutor sitting at this table," Caccaviello said during a debate in August.
 
Caccaviello began talking more about cases that he tried and how it changed his perspective. He talked more about vicious criminals he put behind bars. 
 
He began emphasizing that the office needs an "even-handed approach" and tried to make the case that every case is different and only hands-on experience in the office prepares one to take the job.
 

Sherriff Thomas Bowler was one of Caccaviello's biggest supporters as two political powerhouses went head to head in this election.
Perhaps Harrington had learned from the Senate race that playing from behind is difficult. In that race, Adam Hinds had built strong early support and Harrington faced an uphill battle. This time, Harrington had come out fast and furious. She was aggressive and built a strong campaign team. She appeared to be running away with the race.
 
"Andrea, you have so little experience that you don't even know what you don't know," Knight said on a hot afternoon in late August in the final debate.
 
Knight slammed Harrington over her resume and Caccaviello joined in. And it took hold.
 
The talk around town was now lining up the resumes. Caccaviello supporters slammed Harrington for only being involved in seven trials. An assistant district attorney dug up the records of her first case and said Harrington asked for a mistrial because she was ineffective as counsel. 
 
"During a jury trial in 2011, she stated to Judge Vrabel: 'Judge, I would like to make a motion for a mistrial based on my ineffective assistance of counsel. This is my first trial as an attorney. And there were just things that I did not anticipate.' (TT 1-84). The jury convicted her client of a felony and her client went to jail. If elected DA, will Harrington's ineffectiveness endanger murder, rape, robbery, and abuse cases due to things that she 'did not anticipate?' " Kelly Mulcahy Kemp, a former Berkshire assistant district attorney, wrote in a letter to The Berkshire Eagle.
 
Harrington defended herself saying she has 15 years in as an attorney, had worked on appeals cases for death row inmates, and beyond that had shown the ability to be a leader in the county, to bring people together to tackle the big issues.
 
But the primary election was fast approaching and Caccaviello had found something that resonated with many voters and gained momentum. The tides were shifting -- but not soon enough.
 
"To everybody who voted for me, who believed in me, who believed together we can build a new future for Berkshire County," Harrington said late at night on Tuesday, Sept. 4 well after the polls closed.
 
"For all the people who did not vote for me, I promise I will work just as hard for you as I work for everybody else."
 
Harrington had done it. In a primary with higher voter turnouts than normal Harrington won by about 700 votes. She fielded the call from Caccaviello conceding the race shortly after 11 p.m. Harrington had inspired a large group of supporters, built a campaign team, ran an effective ground game, and put forth a platform that voters supported.
 
She felt she had taken on the establishment and won. There would be no other candidates listed on the November general election ballot. She had broken a glass ceiling to become the first woman district attorney in the county's history.
 
She told Caccaviello that when he was ready, they could work on a transition plan. But that call never came.
 
Weeks went by and Caccaviello hadn't been in touch to set up a transition plan. On Sept. 19, Caccaviello released a statement to the media.
 
"Many of the voters who have reached out to me over the last two weeks have expressed two common concerns: the importance of a candidate's experience and demonstrated accomplishments, and what they view as money, support, and political influence on the race from outside of Berkshire County, I share those concerns and vow to redouble my efforts to keep the office of the district attorney accountable to the people we serve and in the hands of competence, experience, and judgment informed by the prosecution of 5,000 plus cases. Public service has always been my calling. I am not a politician; I am a professional career prosecutor for the public that I have honorably served for thirty years," Caccaviello wrote.
 
"To this end, I am answering the call from these grassroots efforts urging me to utilize the democratic process that allows us to continue to run for District Attorney as a write-in candidate on the November ballot."
 
Though the primary campaign was short timewise, it felt like long. It was tough and became nasty -- a "street fight" as Mayor Linda Tyer would later describe it.
 
Caccaviello revamped his campaign team and moved his campaign office. He raised a lot more money. And he started advertising everywhere he could. He was building what he called a bipartisan campaign and believed that many voters hadn't a chance to weigh in on such an important position. He emphasized that despite running in the Democratic primary, he was "apolitical" and the office should be non-partisan.
 
On Oct. 16, Knight formally endorsed Caccaviello's write-in campaign, against her own party's nominee. 
 
"This is probably not the best political thing for me to do. I know I will be criticized ... but this is the right thing to do," Knight said.
 
Knight believed Harrington didn't have the experience to run the office effectively and that Caccaviello would implement the progressive ideas that she has pushed for so long. 

Following the primary, Judith Knight gave her support to Caccaviello.

The frustrations between the camps began to play out again in public.

City Councilor Melissa Mazzeo levied allegations that Harrington had threatened her politically. Arguments between supporters of both candidates broke out on social media.

Some of Caccaviello's supporters had posted offensive of messages on Facebook and Caccaviello himself had to step in to try to tone it down.

"My campaign (including myself) will not and does not condone or support any message, post, or activity that is divisive, destructive, or just plain offensive. I urge my supporters to talk about my experience and the Write-in process in these final days. We will be successful because of their dedication and understanding of what is best for Berkshire County," Caccaviello wrote on Facebook on Oct. 27.
 
Both camps felt the other was playing dirty and supporters in each camp had no qualms about defending themselves and firing back.
 
Some of Harrington's supporters meanwhile were frustrated with Caccaviello. They saw his write-in campaign as an affront to democracy. Typically the loser of any party's primary makes amends and rallies their supporters around the winner.
 
He had used the Democratic Party, in their opinion, to seek a political position. And frustration among Democrats grew exponentially when it was revealed that the Berkshire County Republican Association had voted to endorse Caccaviello, and Caccaviello welcomed their support.
 
"It is now crystal clear that Paul Caccaviello used the Democratic Party as a way to assure what he perceived as an easy path to get elected. Why should this be a surprise as he was never a Democrat and his positions throughout the campaign demonstrated that?" wrote North Adams City Councilor Marie T. Harpin in a letter to iBerkshires.
 
Caccaviello had always maintained that the job should be non-partisan, but had changed his unenrolled status just before pulling papers in order to run as a Democrat. He said that switch was for "purely practical reasons."
 
In the Berkshires, the Democratic primary is often the election. Other parties without a primary get little attention and the winner of the Democratic primary often cruises to victory. Caccaviello had seen running in the Democratic primary as the most practical way to get in front of voters early and to get into debates and forums.
 
"The district attorney is for everyone regardless of a political party," Caccaviello said of the support from Republicans. "They really share the same view that it is public safety and not politics."
 
Leading Democrats not only locally but throughout the state solidified their support for Harrington from Elizabeth Warren to Richard Neal to Maura Healey to Tyer and city councilors, the Berkshire Brigades, and supporters throughout the county.
 
The twists and turns had raised questions about how this second race might play out. Would focus on Harrington's lack of prosecutorial experience cancel out the progressive vision that had propelled her to victory in the primary? Would Knight's supporters follow her, support Harrington or sit the election out? Would Caccaviello's Republican endorsement anger the larger Democratic base? 
 
Harrington's campaign felt it had already fought and won on the issues during the primary and rejected the idea of holding more debates to allow Caccaviello a free forum to go after her. Caccaviello blasted Harrington for avoiding a one-on-one debate that he felt would give him the chance to demonstrate his command of the court system.
 
Caccaviello accused Harrington's campaign of telling voters there is no write-in process -- an allegation refuted by Harrington supporters.
 
The October surprise hit on Oct. 31. WAMC and Greylock Glass, a Williamstown-based news site, were both diving into details of alleged rapes on the Williams College campus dating back several years. The articles accused the district attorney's office of not following up on reported abuses and, in one particular case, an attorney (who was backing Harrington) claimed evidence in his client's case was illegally destroyed. 
 
Greylock Glass obtained documents relating to that case that made it appear there was enough evidence to pursue it. Opponents said Caccaviello had sought justice in only one of 47 alleged sexual assaults on campus.
 
Caccaviello responded saying Williamstown Police had investigated the matter and determined there wasn't probable cause to pursue criminal charges in the specific case cited by Greylock Glass. In others, there was either a lack of evidence or the alleged victim did not want to go forward with charges.
 

City Councilor John Krol, a Harrington supporter, found himself in the middle of the fray because of his Facebook Live show.
The criticism of Caccaviello's handling of sexual assault on campus came at the same time as other reports about a murder conviction that had been overturned.
 
"In 2008, a criminal defendant was convicted of second-degree murder in the Berkshire County Superior Court. The prosecuting attorney was Paul Caccaviello. The Supreme Judicial Court of Massachusetts overturned the conviction due to ADA Caccaviello's 'improper exclusion of an African-American juror from the jury pool. Because we conclude that the Commonwealth did not meet its burden of demonstrating a race-neutral, individualized basis for its peremptory challenge, we reverse the defendant's conviction,' " wrote Jennifer Breen in a letter to The Berkshire Edge.
 
Caccaviello wanted the campaign to be about his experience but the focus shifted toward perceived failures during his time as first assistant.
 
City clerks were making preparations to deal with hundreds, if not thousands, of write-in ballots as Tuesday's election approached. Pittsfield City Clerk Michele Benjamin would be in charge of the most write-in ballots and said results might not be known for days if the race was close.
 
The rain came pouring down that Tuesday, some streets were flooding, what was left of fall foliage was being knocked off the trees by heavy raindrops. But at every polling location, there were dedicated supporters of both campaigns toughing out the weather to support their candidate.
 
The write-in campaign by Caccaviello caused some jamming problems with the voting machines in Pittsfield. Poll workers, joined by a police officer, had to routinely pack up the ballots from the bin they dropped into and secure them. 
 
"A lot of them have been jamming because of so many write-ins," Benjamin said.
 
Another issue was campaign literature being left behind. Caccaviello had handed out business cards so voters would know how to spell his name and clerks reported they were being left behind in the voting booths. Poll workers routinely do sweeps of the voting booths to remove any such material. 
 
In Lanesborough, a voter also reported a sample ballot hanging in one of the booths had been completely filled in — with all Republican candidates colored in and showing how to write Caccaviello in. 
 
Overall, however, Benjamin said the amount of campaign literature being left behind was less than she expected. No major problems were reported from polling stations.
 
In total there are 89,815 registered voters in Berkshire County and every clerk was reporting high turnout numbers. The number of votes being cast easily exceeded a typical mid-term election and approached presidential election levels. Pittsfield reported 58 percent, North Adams 45, and Cheshire and Clarksburg were both at 63.
 
At the Tavern at the A, former City Councilor Barry Clairmont, part of the Harrington campaign team, was collecting numbers. He added up the total number of write-ins reported with the number of ballot blanks and assumed all of those would go to Caccaviello to be safe. But in every case, Harrington still had more votes.
 

On Nov. 6, Harrington claimed victory at the Tavern at the A.
The numbers for most of the largest districts were in and Harrington held a 5,700 vote lead. Clairmont was ready to call it and did. To a room full of cheers, Clairmont confidently said there was no way Caccaviello could make up those votes. 
 
And the crowd went crazy.
 
The cheers of "Andrea, Andrea, Andrea" picked up at about 9:30, when Harrington's husband, Tim Walsh, entered full of energy with their son on his shoulders.
 
Harrington followed with cameras flashing, phones taking video, and supporters going in for hugs. 
 
She took to the stage and she claimed victory.
 
"I am truly humbled by this opportunity and I make a promise to the people here today and the people of this community that I will always work for the best interest of Berkshire County," Harrington said.
 
The night hadn't been as late as many expected because, in just about every town, Harrington's numbers were above what Caccaviello could get. The race was over and while Caccaviello hadn't yet conceded, Harrington knew it and celebrated. 
 
Caccaviello wasn't willing to concede that night. He wanted those final numbers before giving up because he believes the position is too important.
 
 "We're in unprecedented territory here. I do need to make sure that what's being projected is actually what's happening," he said at a far less cheerful Mazzeo's. "People care about the position, they believe in me, I believe in them. ... We've had thousands and thousands of people expressing their view that experience matters." 
 
On Wednesday, he conceded.
 
The twists and turns of this race have shown one thing for certain: nothing should be considered expected. But for now, Harrington believes she won.
 
Again.
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