Mysterious election mailings likely violated campaign finance laws. Who is behind them?

For the last two years, a mysterious postcard has appeared in the mailboxes of some Brookline residents shortly before the May town election.

Endorsing local candidates and carrying an anti-tax message, the letters have purported to come from the Horace James Civic Association, a South Brookline neighborhood group which newspaper records show was active in at least the 1970s through 1990s, but which appears to have been largely dormant since and has no digital footprint.

No individuals have put their names to the modern day iteration of the association – and it appears to be violating a state campaign finance law that requires groups that spend money to support candidates to register with state or local authorities.

“Money spent to support or oppose candidates generally needs to be disclosed, by filing forms with the town clerk,” said Jason Tait, a spokesperson for the state Office of Campaign and Political Finance, in an email to Brookline.News.

Town Clerk Ben Kaufman confirmed that he has not received any campaign finance paperwork from the association. “I am working with the Office of Campaign and Political Finance on this situation,” he said.

Last year, in a message stating opposition to “massive tax increases,” the group endorsed David Pearlman for Select Board, who went on to win the seat. Its endorsed School Committee candidates, Carolyn Thall and Jesse Hefter, were also victorious.

This year, in a flyer with similar messaging opposing future tax overrides, the group has endorsed Carlos Ridruejo for Select Board, touting his vote against a tax increase to fund the Pierce School building project. (Pearlman also endorsed Ridruejo).

Ridruejo said in an email to Brookline.News that he “doesn’t know much about the group” and was not aware of the flyer until a neighbor told him about it. Pearlman also told Brookline.News he does not know who runs the group’s modern iteration.

The association appears to be expanding its efforts: Last year’s postcard endorsed Town Meeting members only in the South Brookline Precinct 16, but this year’s mailing features endorsements for all 17 precincts in town.

Other organizations endorsing candidates in Brookline – like Brookline by Design, Brookline for Everyone or Brookline PAX – have easily-found websites where the names of leaders or members are prominently displayed.

Who runs the HJCA?

“Horace James was a longtime member of the Brookline Select Board and the HJCA has a decades-long history of supporting fiscally responsible candidates in town elections,” says the back of this year’s flyer.

(James served on the board for more than three decades in the late 19th century).

The address for the Horace James Civic Association, listed on the mailer as 320 Woodland Road, was the former address of Deborah Rudman, a former Town Meeting member who was one of the leaders of the association in past decades – a 1979 local newspaper article mentions her role as its vice president.

Rudman, who is 94 according to public records, sold the home to an LLC in April 2024, deed records show. She last ran for Town Meeting in 2012. She could not be reached for comment.

Newspaper records show that the civic activity of the original group appeared to largely be endorsing local candidates, holding forums, and sometimes weighing in on issues, like opposing the construction of a municipal facility on Hammond Street.

Hardly any information comes up in modern public records when searching for the organization’s name.

One piece of evidence suggested a possible connection to a current Town Meeting member, Jane Flanagan, who listed her membership in the association on her CV when running for office in the past, including in a 2019 voter’s guide.

But Flanagan, who is also the treasurer for Ridruejo’s campaign, said in an email to Brookline.News that she is not currently involved with the group and not responsible for the mailers that went out.