Cheshire Retirement Board

Cheshire Retirement Board

The Cheshire Retirement Board administers the defined-benefit pensions for the Town of Cheshire, Connecticut's municipal workforce. Its structure is defined by three separate plans — the Town Plan, Police Plan, and Volunteer Firefighter Plan — each with its own actuarial assumptions and beneficiary profile. This segmentation distinguishes it from a generic municipal plan, requiring investment and administrative oversight that balances the needs of general employees with the specialized benefit structures of public-safety personnel. The Board's investment posture centers on buyout and special-situations allocations within a conservative municipal framework. While public-transparency filings detail the fund's broad asset mix, the strategy reflects the cautious liquidity and return targets typical of Connecticut local pension systems. Chairman Michael Damian Evans, who leads the Board and also operates Evans Group Financial Advisors, works alongside Finance Director James Jaskot and Deputy Finance Director Gina DeFilio — the two staff officers responsible for day-to-day financial administration and reporting. The fund's estimated $91 million asset base places it in the small-plan tier among US municipal pensions, where resource constraints often heighten reliance on external consultants for manager selection and asset allocation. Despite its modest scale, the Finance Department has earned the Government Finance Officers Association Certificate of Achievement for Excellence in Financial Reporting for over two decades, signaling sustained institutional discipline in transparency and accounting. What makes the Board structurally distinct is its governance model: a volunteer board chaired by a local financial advisor, supported by career municipal finance staff. This hybrid of appointed fiduciary oversight and professional administration creates a checks-and-balances dynamic that both protects against single-point decision-making and introduces a layer of relationship-driven sourcing for external managers and co-investment opportunities.