After graduating from The College of The Holy Cross in 1960, Jerry was commissioned an Ensign in the US Navy.
While serving as Selectman of the Town of Lee from 1966 to 1969, Jerry worked closely with James Hannon who was then Town Counsel for Lee. Their close relationship sparked his interest in a career in law. He returned to school, graduating cum laude from Western New England School of Law in 1973, then joined the firm in 1974.
In 1980 Jerry was appointed Town Counsel for the Town of Lee, a position he held until his retirement in 2007. He also served as Town Counsel for the towns of Sandisfield, New Marlboro, Otis, Egremont, Tyringham, Sheffield, Lenox, Monterey, Savoy and Tolland.