Government gadfly extraordinaire

Ronald Alexander’s ‘remarkable ability to piss people off’

RONALD ALEXANDER of Wellesley says he files open meeting law complaints and public records requests as a hobby, but some think that hobby has morphed into an obsession.

Alexander has filed so many open meeting law complaints with Attorney General Maura Healey that she recently took the unheard of step of refusing to process the overwhelming majority of them and daring him to sue her if he doesn’t like it.

He files so many public records requests and appeals that a number of municipalities have accused him of harassment. The town of Wellesley even won a state ruling that Alexander’s pursuit of certain school committee documents was “part of a series of contemporaneous requests that are frivolous or designed to intimidate or harass.”

And Alexander so frightened one Wellesley school teacher with his efforts to obtain information from her that she sought a restraining order against him. A settlement agreement was eventually reached in which Alexander was required to apologize to her.

The self-employed, 58-year-old software engineer seems to thrive on confrontation – and the attention it brings him. He even tried to leverage that attention into a run for public office. In vintage Alexander style, he ran for two Wellesley town offices at the same time – town clerk and school committee. He lost both, garnering 11.6 percent and 10 percent of the vote, respectively.

Alexander sees himself as a crusader for transparency and accountability in government. In Wellesley, for example, he said his efforts prompted the school committee to post their meeting minutes in a complete and timely manner. But it’s pretty clear that at times his emotions get the better of him.

Some of Alexander’s relentless, shoot-from-the hip tactics, captured on YouTube, make him come across as a bully and a know-it-all. He is also not above speaking rather coarsely at public meetings. But he said he finds it difficult to dial back his personality.

 “I don’t appear to have that ability,” he said. “I do know I have a remarkable ability to piss people off.”


 Alexander has filed public records requests in about a dozen Massachusetts cities and towns, but it’s in Wellesley and Natick where he has focused most of his attention.

In his hometown of Wellesley, Alexander has filed 106 public records requests and 43 public records appeals in 2016 and 2017 – none  in 2018 and 2019. He has won 29 of his 43 appeals.

In Natick, he has filed 121 public records requests and 37 public records appeals over the past two years – winning 35 of the 37 appeals. He also filed with the attorney general’s office a whopping 603 open meeting law complaints in 2018 against the Natick School Committee, which is twice the typical number of complaints filed with her office in a year.

Alexander’s public records requests seek copies of items such as expense records, email exchanges between officials, and litigation documents. His open meeting law complaints typically deal with matters such as meeting notices, executive sessions, outside deliberations, and minutes of meetings.

He also assists others with public records requests from time to time. A mother of two special-needs children saids Alexander helped her obtain records she needed from Natick. “He’s a role model for being a good citizen,” said Karin Sutter. “There are just as many people in Natick that are very happy with what he’s doing as there are those who are upset with him.”

Alexander said he tries to be a force for good. “You know, I’m a white knight helping damsels in distress,” he said. “If good people aren’t willing to stand up and help people who can’t help themselves, what good are they?”


Not everyone sees Alexander as a white knight, however. Many view him as a prickly, arrogant showboater.

“He’s won’t stop harassing us,” said Natick town clerk Diane Packer. “It never ends with him.”

Timothy Luff, the assistant school superintendent in Natick, said Alexander continuously disrupts school committee proceedings. “He’s on a vendetta and is out to get us, plain and simple.”

Ronald Alexander

At a meeting of the Natick School Committee in March 2018, Alexander brought a ukulele to the podium and sang “Oh where, oh where has the superintendent gone?” The school committee was not amused. After a contentious exchange with Alexander, they stood up and walked out. “I’ll be waiting for you when you get back,” Alexander taunted. Police officers were eventually called to the meeting.

At another meeting in November 2018, Alexander mentioned someone’s penis. The shocked committee chair, Lisa Tabenkin, tried to silence him. When he wouldn’t relent, she and the other members of the committee stood up again and walked out.


Taking advantage of a provision in the open meeting law, Natick put up $2,500 to hire an outside mediator to resolve all the open meeting law complaints Alexander filed against the school committee. The mediation failed when the parties were unable to agree on a resolution. As a result, the complaints were referred to the attorney general’s division of open government.

Carrie Benedon, the director of the division, told Alexander her office would review only 15 of the 603 complaints, and he could choose the 15. (Alexander provided the email correspondence to CommonWealth.)

“We do not believe that [your] motivation in filing such a large volume of complaints was based on a good-faith effort to ensure the [school] committee’s compliance with the open meeting law,” Benedon wrote to Alexander.

“There’s a big problem with what you are doing,” Alexander fired back. “It’s against the law.” For good measure, he called Benedon “delusional” and said she is in need of a “full psychological examination.”

A colleague of Benedon’s, Juliana deHaan Rice, deputy chief of Healey’s government affairs bureau, told Alexander the office wasn’t budging. “If you wish to challenge the division’s procedures in a judicial forum, you are of course free to explore this option,” she wrote to him.

In a rare moment of waving the white flag, Alexander decided to go along with what the attorney general had laid out.

The 15 complaints Alexander wound up submitting last December alleged 29 violations of the open meeting law. Last month, Healey’s office ruled that 14 of the 29 were indeed violations of the law.

The violations included improper deliberation by email, failing to properly respond to a request for minutes of meetings, not recording a roll call vote in the minutes, and failing to comply with procedural requirements for convening an executive session.

Benedon said she was confident Natick would comply with the open meeting law moving forward, but warned that “similar future violations may be considered evidence of intent to violate the law,” which could result in fines being imposed.


In Wellesley, officials have tried for the most part to fulfill Alexander’s requests, spending nearly $75,000 on various outside lawyers in 2016 and 2017 to respond to his public record requests and appeals.

Occasionally, Wellesley has gone on offense. At one point, town officials sought and won approval from the state’s supervisor of public records to ignore an Alexander request by tapping a provision in state law that allows record holders to deny a request if it is “part of a series of contemporaneous requests that are frivolous or designed to intimidate or harass.”

Alexander’s pursuit of public records began in 2013, when Elizabeth Perry, the Wellesley school system’s director of performing arts, reassigned an orchestra teacher from high school to elementary school – a move that Alexander, who had a child in the school’s orchestra program at the time, strongly opposed.

To learn why the transfer was made, Alexander filed a public records request, but he had trouble obtaining the records he needed. That personal experience triggered what he describes as a six-year campaign for greater government transparency and accountability.

In 2013, Perry went to court to seek a “harassment protection order” against Alexander after feeling intimidated by communications she received from him. It was reported that Wellesley paid for Perry’s legal expenses.

Alexander and Perry subsequently entered into a settlement agreement in which Alexander agreed to immediately cease criticizing the school system and to write a mea culpa to Perry.

Alexander apologized to Perry and said he never intended to intimidate her. He said he was a father who loves his children and wants what’s best for them.

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“I am not a politician and I am clearly not a diplomat,” Alexander said in his letter. “I realize now that some of the approaches that I took . . . were not the best choices that I could have made, and I have likely offended more than a few people, lost a few friends, and brought embarrassment to my wife and family.”

Yet Alexander makes no apologies for his take-no-prisoners style. “I give them the chance to do the right thing,” he said. “But then when they don’t respond to my request for records or withhold them or don’t follow the provisions of the open meeting law, I just say, ‘OK, you know, I can make nice, but if you’re going to play around with me, it’s game on, gloves off.  You don’t know who you’re screwing with here.’”