Maldonado Leaving District Courthouse

It will be far more than just a job Judge Diana Maldonado will give up when she leaves Chelsea District Court this week for a new appointment at the state Appeals Court in Boston’s John Adams Courthouse.

Maldonado started her career as an associate justice in Chelsea in 1998 and will end her run here this week as the First Justice of the court – in between making a lot of friends and transforming the way the court handles its surging number of drug cases. Admittedly not knowing a lot about the communities when she was appointed by then-Gov. Paul Cellucci in 1998, she said she has come to embrace them, both inside and outside of the courthouse.

“I have really gotten to know these communities,” she said during an interview last Friday in her court office. “Even though I live in JP, everything I do, I do in Chelsea or Revere. My car gets serviced here in Chelsea. I get my pasta, pizza and Italian food in Revere. What will I do without Luberto’s? I do my shopping in Chelsea. I worked here and a lot of my day-to-day stuff was done in Chelsea and Revere. It has become so much a part of my life and I’ve made a lot of friends.”


Maldonado said she was still torn by the decision to leave – even after she had applied for the Appeals Court opening and was going through the confirmation process.

“It’s hard to leave,” she said. “I love the work here. I love the interactions. Sometimes, part of your job is not just getting up and applying the law and that’s it.”

As an example, she recounted a time when – during a rather mundane eviction hearing – she got so fed up with the back and forth between the tenant, landlord and their attorneys, that she actually ended up addressed 100 envelopes from the bench so that the rent payments would get to the right place.

“I had them go out right there to the CVS and get a box of envelopes so that we could straighten out the problem then and there,” she said. “The tenant took the first envelope and filled it out in front of the lawyers. They brought it up to me and it couldn’t be read. In the end, the problem was that he was dyslexic and illiterate and you couldn’t tell what he wrote. So, I took the rest of the envelopes and addressed them right on the bench. They still joke about that to this day, and they call me the ‘envelope judge.’ But, they haven’t been back either. I’m going to miss going the extra mile to find out what’s going on and how to resolve it.”

However, she also said she knows it is time for a change – both personally and professionally.

She gave three reasons.

“First, I think it’s time for me to find a new challenge,” she said. “My second reason is I’m the mother of a young child and I have a husband (in the military) in Afghanistan. The Appeals Court offers more work, but it also offers me different, more flexible hours.”

The third reason is more sentimental, kind of a returning to her roots. Right out of law school, Maldonado was a law clerk for Appeals Court Judge Frederick Brown. She spent a few years clerking for him and said she developed quite a lot of respect for the experienced jurist. Now, as fate would have it, Browne is retired but has been recalled. So, she will have gone full circle with him, from clerk to colleague.

“I started out as a clerk in the Appeals Court,” she said. “Nothing would give me more honor than to go back as a colleague of his and serve under his mentorship.”


Maldonado grew up in humble beginnings, one in a family of 10 children growing up in the South Bronx. Though her parents were from Puerto Rico and not a foreign country, she said she identifies with many of Chelsea’s immigrant families – having spoken Spanish at home and English at school when she was growing up.

She said her family always knew she would be a lawyer because she was addicted to ‘Perry Mason’ and she would always argue.

“They would always say, ‘Don’t argue with her, everyone knows she’s going to be a lawyer,’” Maldonado recalled.

In fact, the idea of her pursuing law was so strong in her family that when she was young, her siblings gave her what they thought was a great Christmas present.

“I wanted a Chatty Cathy doll for Christmas, but my siblings had convinced my parents to get me a copy of ‘Clarence Darrow for the Defense’ and a copy of the Constitution,” she said. “They thought I  would love it. I opened it and cried and cried. They had to run out and buy the Chatty Cathy. I was 11 and they gave me a book and a dingy piece of paper? No way.”

She said it was the raw experiences of the streets outside her home that shaped how she would later approach drug crimes.

She recalled being an insomniac and watching people in the streets who were on drugs and doing crazy things – such as breaking into abandoned buildings and stealing copper. She also recalled seeing men cooking heroin on the steps of her friend’s building, and also not being able to walk alone with her friend only two doors down.

Though it shaped her, it didn’t consume her.

After attending Stony Brook University in New York, Maldonado spent two years working in the legal department at JC Penny’s. Afterward, she left for Boston’s Northeastern University Law School.

During that time, she became a law clerk for Judge Brown, and after a two-year stint in an innovative defense attorney program in New York City, Maldonado returned to Boston and became a Federal Defender. In fact, she was the first Hispanic federal defender in the Boston office – which turned the heads of many people in the state’s judicial circles.

It wasn’t long before she was given a nudge to apply for the Chelsea judgeship position – and the rest is history.


Maldonado said she never had any personal experience with drugs in her family or in her own life. However, the experiences she had in her neighborhood – as referenced above – made her petrified of drugs and their affects.

So, it was with that as a background that she went on to establish the cutting-edge drug court at Chelsea District Court.

“While I wasn’t directly affected, I had been indirectly affected by what a drug can do to a community – not just to a family, but to a community,” she said. “As a kid, I had to figure out when I was going inside because a whole different world took place outside after a certain time of night and also we had the needles on the street…We couldn’t walk two doors down by ourselves because something might happen. I was petrified by drugs.”

Right off the bat, Judge Tim Gailey gave Maldonado a shot at establishing a drug court in Chelsea – something that had not yet been perfected and was only a crude experiment in a few courts around the country.

The result from Chelsea Court’s experiment was the perfect marriage between treatment and the courts. Maldonado said it’s a process that builds up a dam of services and prevents the addict – like water – from escaping the fortress built around them.

Better yet, it worked, with her efforts showing the offenders only repeated 20 percent of the time when in Drug Court – as opposed to 80 percent of the time without the specialized court.

“Everyone here put their heart and soul into it and we built a national reputation,” she said. “If you ask the judge who runs the federal drug court, he’ll tell you he modeled it after Chelsea…If there’s any mark I made here, clearly it’s the experience of the drug court in Chelsea and Revere. That was a big part of what I did here.”


Last Friday, boxes lined the walls of Judge Maldonado’s office, each holding a piece of paper that read ‘Appeals Court.’ Pictures, videotapes, books and thank you cards – literally 14 years of professional work – were being swept up into storage boxes to be transferred to a new office in downtown Boston.

It was a bittersweet scene for Maldonado.

“There’s no question in my mind I’m going to miss the good things, the dramas and being able to really make a difference with the little things that matter to people’s lives,” she concluded.

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