James Edward Roberts

James Edward Roberts, 80, of Trumbull, CT died at home May 29, 2026, in the care of his wife of 58 years, Agnes (Nessy) Sharp Roberts, and Hospice at Home.

The son of Kenneth M. Roberts and Maude Caswell Roberts (later Swan), Jim was born in Bridgeport, CT, and attended local schools. He graduated from Fairfield Preparatory School and from Cornell University in 1968 with a degree in government and German, on a four-year Dean’s scholarship.

Immediately after graduation, he enlisted in the U S Army and served four years in its Security Agency. He learned Arabic at the Defense Language School in Monterey, CA and was assigned for two years in Asmara, Ethiopia, directing a twelve-person intelligence team. Nessy joined him there in 1969 as his new bride. He finished his tour of duty in Washington, DC and then began work as a commercial casualty underwriter in New York City. He moved to progressively larger responsibilities, in a newly formed division of American International Group; in Rollins Burdick Hunter; and in North Star Reinsurance as Senior Vice President.

He joined Re Capital Corporation in 1986 as one of three founding officers, serving as its president and CEO. Later positions were chairman and CEO of Trenwick Group, Ltd.; executive Vice President of Alea North America reinsurance division; President of AequiCap Insurance Group; and finally chairman and CEO of Tower Reinsurance, Ltd., retiring in 2014. He was known and respected for his business acumen, uncompromising integrity, and fair dealings.

Jim and Nessy treasured a wide circle of friends in the U S and abroad. His hospitality and generosity were justly celebrated, along with his extensive knowledge of fine wines and a sense of humor that would often produce verbatim renditions of scenes from ‘Monty Python’ and ‘Fawlty Towers,’ complete with accurate accents.

With Nessy, he was especially close to fellow parishioners at St. Paul’s Episcopal Church in Fairfield, where he served as a lay officer and active member, supporting particularly its music program and service programs in Bridgeport. He enthusiastically supported Nessy in her career as a water-colorist, photographing favorite sites they visited in France and the UK that became subjects for her art.

He delighted in welcoming all creatures great and small from the woodlands around his home--deer, foxes, coyotes, flocks of songbirds, crows, turkeys, and ravens; a red squirrel that became a house guest; and a bear and her two cubs enjoying the swimming pool.

He loved being outdoors, saying it kept him sane, and even when in the early days money was tight declared he’d rather buy hiking gear than furniture. He developed a passion for wintertime mountain and ice-climbing and once, with Nessy, summited Mt. Katahdin in an ice storm. With his other favorite climbing companion, Nessy’s nephew Erich Bentz, he climbed Alpine peaks in Austria and France, their climbing capstone being Mt. Elbrus in the then-Soviet Union.

Nessy’s cousin Shannon Gerrity and Erich’s wife Theresa Bentz provided invaluable care and support during Jim’s last illness. From a very small family, Jim loved the “crazy Gerrity clan,” as they called themselves. Along with Erich Bentz and his father Russell Bentz (wife Teddi Davis), survivors include Nessy’s sister Suzanne Bentz, her cousin Glen Gerrity and his wife Dawn Gerrity, Jimmy and Alex Gerrity, Brian Gerrity and Marcus Lazzaro, Roger Gerrity, and Dawn Ann Gerrity; and a wide circle of friends and business associates who will treasure his mentorship, his friendship, and his example.

A memorial service will be conducted on Saturday, June 13 at 11:00 at St. Paul’s Episcopal Church, 661 Old Post Rd, Fairfield.

Donations to the St. John’s Family Center, 1067 Park Ave, Bridgeport, CT 06604 will be gratefully received and will aptly honor Jim’s memory through supporting one of his abiding concerns. Please note “In memory of Jim Roberts” in the memo line of checks.