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The debate at Conte Community School was well attended.

District Attorney Candidates Display Differences in Lengthy Debate

By Andy McKeeveriBerkshires Staff
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Andrea Harrington promised to be a leader who inspires others to address the issues.
PITTSFIELD, Mass. — Judith Knight says she has "shown you what I am."
 
On Wednesday night, the candidate for district attorney boasted of some 30 years of work in the community. She stood as a defense attorney more than a dozen years ago for teenagers for whom she believed were inappropriately getting the book thrown at them from former District Attorney David Capeless for selling marijuana.
 
When those from the West Side neighborhood felt the same injustice was being served on young woman in 2007, Knight showed up again. In 2008, there was a similar call. In 2012, after a melee at Third Thursday that resulted in three black men wrongly arrested, she again was there.
 
She fought those cases on behalf of the community, she said, because that's what she feels is her calling -- to serve the community. 
 
"I have shown up for this community. For this community, for South County, for North County. That is called commitment," Knight said. "I've shown you what I am."
 
Commitment is the one word she would use to describe her candidacy for the position. Paul Caccaviello uses the word "experience" for his.
 
"I am not running on five months of being the district attorney. I am running on 29, nearly 30 years of service," Caccaviello said. 
 
The current district attorney, after being appointed the position when Capeless resigned early to allow him to run as an incumbent, has worked his way from the lowest level of the prosecutor's office to the top and is now seeking to be rightfully elected to the post. He says the experience he has gained along the way has taught him when to show compassion and when to demand consequences. 
 
"Often it is a mix, you learn that from doing this work and I've been doing that for 30 years," Caccaviello said.
 
Tenacity. That's how Andrea Harrington characterizes her campaign.
 
She grew up in a working-class family and went into law as a criminal defense attorney. She represented those on death row in the state of Florida and returned to the Berkshires to raise a family and continue on as a defense attorney. In that job, she's watched what she sees as the Berkshires going the wrong way in battling crime -- citing high incarceration rates and what she describes as the criminalization of people dealing with mental health issues or poverty. 
 
"I've been very disturbed by what I've been seeing in the courts in our community," Harrington said. "We need a district attorney that is going to work together with this community to address the most pressing issues we face here."
 
She said the efforts under Capeless and Caccaviello haven't been effective. And if the county wants to see criminal justice reform, "they need a reformer."
 
She gestured to a large number of people in the audience wearing campaign shirts and noted those holding signs on Onota Street outside of Conte Community School saying she is the one who can inspire reform and the leader in Berkshire County.
 
"It is going to take somebody who has the energy, the ability to inspire people, and the work ethic in order to accomplish that," Harrington said.
 
The three met Wednesday night in the school's packed gymnasium for a debate hosted by the local branch of the NAACP. For two hours, the three Democratic candidates made their case to voters as to why they should be elected.
 
While Harrington attempted to make the case that new blood is needed in the office to get rid of "the old guard," she has been dogged throughout the campaign by the question of experience.
 
Both Caccaviello and Knight stressed the importance of working as a prosecutor and both of them can boast of experiences doing that whereas Harrington cannot. 
 
"I am the only candidate here who has been on both sides of the courtroom," Knight said. 
 
Knight said somebody without experience as a prosecutor doesn't truly know what it takes to bring a case to trial. It is particularly important in Superior Court cases "that make us lock our doors at night." 
 
"It is easy to look from the outside and throw stones but when you are on the inside, you know how to change the criminal justice system," she said.
 
Caccaviello said the district attorney's job isn't just any prosecutorial job, it is the county's top. He's prosecuted more than a dozen homicides and a number of rape and domestic violence cases. He's been at crime scenes at 2 a.m. because he's seen how that ultimately helps in the courtroom.
 
"This is the chief prosecutor's job in the county. Just from a common sense standpoint, having experience in the field is of paramount importance," Caccaviello said. 
 
That experience is what grows relationships with the police investigating the crime, making sure they know they can count on the district attorney to get the job done, said Caccaviello, who just reeled in an endorsement from the Pittsfield Police unions.
 
But what exactly has that experience brought to Berkshire County to date? Harrington said there is a "staggering" opioid crisis, that North Adams has the highest per capita crime rate in the state, that there are 23 percent more domestic-violence prevention order requests in the Berkshires than the rest of the state.
 
Her experience has been that the current district attorney's office has had no interest in implementing different ideas, and had even fought against the state's criminal justice reform bill. 
 
"We've had a district attorney's office that doesn't have a diversion program," Harrington said.
 
From her 15 years as an attorney, she said it is important to have a district attorney who doesn't rush to judgment, who has an understanding of an individual's circumstances and who has the integrity to be just in prosecution.
 

Paul Caccaviello places most of his emphasis on his experience.
She characterized the current district attorney's office as being too heavily focused on getting convictions than curbing crime from happening in the first place.
 
"The old way of approaching criminal justice is not working for this community. I intend to take a broader approach," Harrington said. 
 
Harrington said there are disparities in how people are treated in the criminal justice system but the office has shown no interest in tracking that data and making adjustments. She said in Berkshire County, African-Americans pay five times the amount for bail than a white person and the rate of incarceration among African-Americans is higher.
 
But the district attorney's office can't provide those numbers because it hadn't been tracking it, she said.
 
"It is a black box. We really don't know if people are being treated fairly regardless of their race because that is not being tracked," she said.
 
That's one of the things she'd do to correct it. She plans on collecting that data and she plans to have a citizens advisory committee in place to help go over those numbers and help address those disparities. Harrington will also end the practice of asking for bail too high for a person to afford as a means to keep them in jail before a trial.
 
Knight said a lot of those issues stem from issues outside of the justice system. She said there is an inherent bias prevalent throughout society. 
 
"It bears out that people of color and people of poverty receive longer sentences," Knight said.
 
She knows of clients who violate probation not out of defiance but because of poverty and personal struggles, which adds to charges and records. She wishes that wasn't the case but said the first step in addressing it is to recognize it and then start battling against it through training to eliminate that bias.
 
Caccaviello somewhat agreed and credited the criminal justice reform bill as going after those disparities. He is supportive of training to rid law enforcement of inherent bias and said he's been talking about implementing such training after the reform bill had passed.
 
"It is not going to be a sprint out of the problem," Caccaviello said. "By the time people end up in the criminal justice system, a lot of things have happened up until that point."
 
All three candidates spoke in favor of ensuring that the personnel in the office reflects the demographics of the community. However, Caccaviello added that doing so can often be tricky because the wages in such an office are lower than other law jobs, which limits the number of applicants. He said hiring a diverse group is an important goal.
 
In managing staff, Knight said she'd like to see the lower level assistant district attorneys stay in a district court longer. She said too often she'll be working on a case with one attorney from the office and then that attorney is shifted to another court. That delays the case even longer, she said. She'd put in a policy that the district court attorneys stay there for at least a year to limit the number of times a case is passed from attorney to attorney. 
 
"The stint in each court is just not long enough," Knight said. "Have them stay at least a year because that is the life of the case, the DA would know the cases well and be getting experience."
 
Caccaviello said the newest hires start in Central Berkshire District Court because that is where there is the most support to answer questions and give advice. From there, the attorney moves to North Adams, where there is still support, but just not as much. And then the attorney goes to Great Barrington, where they are mostly on their own. 
 
"That is the best training ground," Caccaviello said of the district courts.
 
Harrington, however, said she'd rather see newer attorneys start in the appellate court and then move to the district. 
 
"That's where you really start to learn the law and get to see what happened in trials that already occurred, you get to see what went well and what went poorly," Harrington said. 
 
She said it is important that there be strong training and oversight to help newer attorneys grow into stronger prosecutors. She wants an office where attorneys feel free to ask questions and continue to strive to improve.
 
Knight agrees with Caccaviello that the best experience comes from the district court. 
 
Maybe of bigger importance to the community as a whole is the rights of victims. Harrington said in the past victims have been discredited and not supported. But, that has been changing nationwide. She cited the #MeToo movement as a sign of the community supporting and trusting victims to help end the cycle of violence. 
 
"We really need to work together to ensure victims get all of the support they need to go through a long and difficult process," Harrington said.
 

Judith Knight boasts of having both the experience and the progressive ideas to change the office.
She promised she would work closely with victims of a crime throughout the entire process and help them follow a case from beginning to end. She cited organizations like Bikers Against Child Abuse that works to empower children who are victims of abuse to not feel afraid as ones she'd like to incorporate in Berkshire County.
 
Caccaviello said his office is "victim-oriented" and that the current staff is highly trained and works closely with community partners to support victims. He said he works hard to make sure a victim is well aware of the process each step of the way and feels supported.
 
"It is a process that demands patience and it frustrates so many," he said. 
 
Knight said support is particularly important in domestic abuse cases. She said she'd implement a policy in which the prosecutor of such a case must stay on it until the end. She said she'd make sure there are mental health experts on staff to help victims and bring in training and teams focused on crimes like child abuse to do the same.
 
Each of the candidates agree that a prosecutor's style ultimately leads to decisions on who gets charged, with what they get charged with, and what goes into a possible plea deal.
 
In reference to the prosecution of her 2006 case of the teenagers selling marijuana, Knight said, "another DA's office wouldn't have done it." 
 
"It was mean and vindictive from the DA's office," she said. 
 
With recreational marijuana laws now passed, Knight said she wouldn't prosecute low-level marijuana crimes at all.
 
"I would not prosecute these marijuana cases. I wouldn't do it. Marijuana is legal, let's not waste our time in the court system," she said.
 
Caccaviello wouldn't go that far. He said if the police found enough illegal marijuana activity to arrest, then he'd take a careful look at the case and prosecute it on a case-by-case basis.
 
Harrington split the middle. She said it is not appropriate or helpful to prosecute low-level marijuana cases. But she is also concerned about the youth's access to marijuana. She doesn't believe in throwing some children in jail for marijuna to protect other children, so she'd look to take another approach toward limiting access to children.
 
Harrington said her style and decision making is why the race is so important. She said 95 percent of the cases in the courts are settled by a plea deal and parameters of jail time, bail amounts, and who and what to charge are all chosen by the office.
 
"This race is so important because we have a very progressive, Democratic community here and it is important we have a district attorney that reflects that," she said. 
 
She said she would prioritize being tough on cases of sexual assault and child abuse, and not allow those to be pleaded down to probation time. 
 
Caccaviello described his style is fearless. He said he took on the challenge of convicting Damien Lamb of murder despite not having a body, going after former priest Gary Mercure for the rape of altar boys, and seeking convictions in the recent triple murder. 
 
"I will not shy away from a challenge. I think everyone deserves justice," Caccaviello said.
 
And despite working closely with police departments, he said he wouldn't shy away from prosecuting an officer for misconduct or excessive force either. He said he has prosecuted officers for excessive force, misconduct, and embezzlement already.
 
"It is a prosecutor's duty, it is their obligation to follow the facts and the law wherever it goes," he said. 
 
Knight said those cases are important in building trust because "they are held to a higher standard and they have to meet the goals we expect them to."
 
She hopes to put in programs that avoid those conflicts in the first place. She said she'd work to bring in programs to ensure police are trained to deal with individuals with mental illness or handle domestic violence cases. She said there are many different situations officers find themselves in on a given day and they need to be well trained in how to avoid escalating the situation.
 
Harrington said she wouldn't go after officers -- she'd have someone else do it. She said the district attorney and the local police work too closely together and the perception that the relationship prevents justice from beginning served against an officer is growing. She said she'd have a policy putting an outside agency in charge of the investigation to ensure there are no conflicts of interest in the investigation and prosecution.
 
Harrington also promised to be transparent with the community. She said she'd be attending community events and speaking to people face to face so that the community knows what is happening in the office. Not only will she have a citizens advisory board, but she also promised to be open and honest with the press.
 
"I do not see the press as the enemy and I will share information with them," she said.
 
Knight agrees that when the media calls, as long as the questions don't jeopardize the investigation then the question should be answered. She also believes it is very important for the office to really show the community the importance of the office.
 
The current district attorney's office hasn't had the most transparent operation. Caccaviello said early on he identified a need to connect with the community more. He said his first calls were to local officials and leaders. He met with them and talked about the issues. He said he then had the office's website revamped and he is starting a Facebook page.
 
The candidates currently have three more debates scheduled -- on Aug. 14, Aug. 20, and Aug. 23 -- ahead of the Sept. 4 Democratic primary. There are no other candidates running so whoever wins the primary will be unopposed on the November ballot.

Tags: debate,   Democrat,   district attorney,   election 2018,   primary,   


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Friday Front Porch Feature: This Luxury Home Has Plenty of Amenities

By Breanna SteeleiBerkshires Staff

LENOX, Mass. — Are you looking for a big house to enjoy your days with a big movie theater, a sauna, and more? Then this is the house for you.

Built in 2004, this seven-bedroom, and nine-bathroom home is 7,073 square feet on more than an acre. The home comes with an elevator to the lower level to access a theater, sauna, gym, wine cellar, massage room, and its very own soda fountain. 

The home also has a guest house with a saltwater pool. A multi-car garage greets you with heated floors.

The this home is listed for $4,950,000 and is located in the 125-acre, gated Pinecroft compound.

We spoke to Leslie Chesloff, the listing agent with William Pitt Sotheby's.

What do you think makes this property stand out in the current market?

Chesloff: This gated Berkshire stone estate truly redefines luxury living in the Berkshires. What sets it apart is the rare combination of resort-style amenities and complete privacy. The property offers Canyon Ranch-level wellness living with a full spa experience at home — including a sauna, massage room, and gym — plus an eight-seat hi-def theater with wine cellar for entertaining. The heated, gunite saltwater pool and spa are complemented by a fully equipped pool house with a guest suite and complete kitchen, perfect for extended family or guests.

What was your first impression when you walked into the home?

The moment you step inside, you're struck by the quality and craftsmanship — those 300-year-old reclaimed timber floors set an immediate tone of authenticity and warmth. The scale is impressive but never overwhelming; this is a home designed for gracious living, not just show. The natural light, cathedral ceilings, and thoughtful flow between spaces create an inviting atmosphere that balances grandeur with genuine comfort.

How would you describe the feel or atmosphere of this home?

This home feels like a private wellness retreat meets sophisticated family estate. There's a serene, spa-like quality throughout — enhanced by features like the sauna, steam shower, and massage room — but it never feels clinical or cold. The Berkshire stone exterior and reclaimed timber floors ground the home in a sense of place and permanence. It's designed for people who appreciate the finer things but want to actually live well — whether that's screening a film in the eight-seat theater with wine from your own cellar, hosting poolside gatherings, or simply unwinding in your own spa sanctuary.

What kind of buyer would this home be ideal for?

This is perfect for the discerning buyer who values wellness, privacy, and culture in equal measure. I envision someone who spends their days hiking or exploring the Berkshires, then comes home to unwind in the sauna or pool. They might entertain guests in the theater wine room, host multi-generational gatherings with family staying in the pool house guest suite (which has a full kitchen), and appreciate being minutes from Tanglewood, world-class dining, and Berkshire arts.

This could be an executive looking for a primary residence with work-from-home flexibility (there's an office/bedroom suite), a wellness-focused family, or empty nesters who want to host adult children and grandchildren in style and comfort.

What would you say to a buyer trying to imagine their life in this space?

Picture Saturday morning: you're sipping coffee on the terrace overlooking your heated saltwater pool, planning a day at Tanglewood. Your guests are making breakfast in the pool house kitchen — they have their own private retreat but are steps away when you're ready to gather. Evening arrives, and you screen a favorite film in your eight-seat theater, selecting a perfect bottle from your wine cellar. This isn't just a home; it's a lifestyle that brings resort-level wellness, entertainment, and hospitality to your doorstep — all within a secure, maintenance-free compound where nature meets luxury.

Are there any standout design features or recent renovations?

Absolutely. The home includes an elevator for multilevel accessibility, which is both practical and forward-thinking. The lower level is exceptionally well-conceived — a true entertainment and wellness wing featuring the eight-seat hi-def theater, wine cellar, sauna, gym, massage room, and even a charming soda fountain. The gourmet kitchen has been recently updated, customized wet bar, while outdoor living is elevated with the heated gunite saltwater pool/spa, firepit, and that incredible pool house with guest suite and full kitchen. Also, new HVAC system and heated driveway.

Thoughtful details like cedar closets, steam showers, central vacuum, and backup generator show this home was built to the highest standards.

You can find out more about this house on its listing here.

*Front Porch Feature brings you an exclusive to some of the houses listed on our real estate page every week. Here we take a bit of a deeper dive into a certain house for sale and ask questions so you don't have to.

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