Fennessey Appointed Permanent Plympton Town Administrator in Split 2-1 Vote Amid Looming $317K Year-End Deficit
PLYMPTON - July 9 and 14, 2026 - The Plympton Board of Selectmen voted 2-1 to appoint Interim Town Administrator Robert “Bob” Fennessey to the permanent position, concluding an intensive search that culminated in a week of public interviews and stark financial revelations. The appointment came immediately after the board wrestled with a late-breaking $317,283.55 year-end fiscal deficit, highlighting the fragile financial tightrope the rural town must walk as it transitions to permanent leadership. While Selectmen Dan Cadogan and Dana Smith prioritized immediate stability and Fennessey’s proven local track record, Chairman Nathaniel Sides disagreed, advocating for a candidate with specialized municipal finance experience to steer the town through its looming budgetary challenges.
The Full Story
The decision to install Fennessey permanently followed a rigorous and highly public screening process. On July 9, 2026, the Board of Selectmen conducted back-to-back public interviews with four finalists selected from a pool of 30 applicants: Christine DeMoranville, Robert Fennessey, Heather Hamilton, and Sydney Viveiros. Each candidate presented a different path forward for Plympton, a right-to-farm community of roughly 3,000 residents that faces a narrow commercial tax base and an aging infrastructure network.
During the July 9 interviews:
Christine DeMoranville, City Treasurer-Collector for Taunton, highlighted her exceptional fiscal background, notably securing Taunton the fourth-highest investment earnings in the Commonwealth in FY25. She pitched herself as an operational manager ready to write Plympton’s first comprehensive employee handbook and formalize departmental policies.
Robert Fennessey pointed to his legal background, his six terms as a Selectman in Plainville, and his experience serving as Town Administrator or Interim Administrator in five other Massachusetts towns including Plympton’s immediate neighbors, Carver, Kingston, and Halifax.
Heather Hamilton, a former Select Board Chair in Brookline, offered massive operational experience, having managed statewide MassDOT fleet assets and secured over $30 million in public grants during her career in the private sector.
Sydney Viveiros, Assistant Town Accountant for Lakeville, delivered a highly prepared, data-driven pitch, highlighting her hands-on familiarity with municipal accounting software, collective bargaining retro-calculations, and senior tax-workoff programs.
When the Selectmen reconvened on July 14, 2026, the gravity of Plympton’s fiscal reality was laid bare before a single vote on the candidates was cast. Town Accountant Lisa presented a year-end deficit report of $317,283.55. The shortfall was driven primarily by a $128,000 deficit in police department salaries and a $78,741.67 overage in the town’s legal budget.
The board successfully resolved the deficit by transferring $61,000 from group health insurance surpluses, $19,000 from the transfer station, and drawing the remainder from the town’s reserve fund. However, the unexpected deficits drew sharp criticism from Chairman Sides, who called for a cultural shift in departmental communication. Sides emphasized that department heads must notify the administration of overages early in the year rather than relying on year-end transfer cleanups.
