As the May town election approaches in Brookline, a puzzling phenomenon has captured local attention. For the past two years, enigmatic postcards have been appearing in residents' mailboxes. These cards advocate for specific candidates and promote an anti-tax agenda, purportedly originating from the Horace James Civic Association (HJCA), a neighborhood organization with roots stretching back to at least the 1970s through the 1990s. Despite its historical activity, the group seems to have faded into obscurity until recently, raising questions about its current leadership and compliance with state campaign finance laws.

The origins of the modern-day HJCA remain shrouded in mystery. The group endorses candidates without disclosing individual members or leaders, which appears to contravene Massachusetts regulations requiring transparency for entities funding political campaigns. According to Jason Tait, spokesperson for the Office of Campaign and Political Finance, any funds used to support or oppose candidates must be disclosed via forms submitted to the appropriate authorities. However, Town Clerk Ben Kaufman confirmed that no relevant paperwork has been filed by the association. Investigations are ongoing in collaboration with state offices to address this potential violation.

In the previous election cycle, the group's messaging opposed significant tax hikes while endorsing David Pearlman, who subsequently won a seat on the Select Board. Their recommended School Committee candidates also triumphed. This year, Carlos Ridruejo received the association's nod for Select Board candidacy, praised for opposing a tax increase tied to the Pierce School project. Both Ridruejo and Pearlman expressed unfamiliarity with the group's operations, having learned about the flyer only after neighbors informed them.

Interestingly, the HJCA appears to be broadening its influence. While last year's endorsements focused solely on South Brookline Precinct 16, this year's outreach encompasses all 17 precincts within Brookline. Other active civic organizations in the area maintain accessible online platforms showcasing their leadership teams, contrasting sharply with the HJCA's opaque nature.

Historical context reveals that Horace James himself served on the Brookline Select Board for over three decades during the late 19th century. His legacy continues to inspire the group's mission of endorsing fiscally prudent candidates. The mailing address provided—320 Woodland Road—once belonged to Deborah Rudman, a former Town Meeting member instrumental in the association's earlier activities. Public records indicate she sold the property to an LLC in April 2024 and has not participated in Town Meeting since 2012. Attempts to contact her were unsuccessful.

While some connections might suggest links to current officials like Jane Flanagan, who mentioned membership in older voter guides, she categorically denies involvement in recent mailings. Her role as treasurer for Ridruejo's campaign further underscores the separation between her duties and the HJCA's actions.

This election season, Brookline voters find themselves confronted with unanswered questions surrounding the resurgence of the Horace James Civic Association. As investigations continue into its legitimacy and adherence to legal standards, the community remains curious about the true identity of those driving its agenda and whether its endorsement carries weight in determining electoral outcomes.