Gennaro A Romano III

Chatham, MA - Gennaro Anthony Romano III, teacher, coach, mentor, fundraiser, died at his home in Chatham, Massachusetts at the age of 76.

The oldest of three brothers, Jerry was born on July 20, 1949 to Gennaro A. Romano Jr. and Joyce H. Bailey. They resided in Derby, Connecticut and the boys attended the local public schools. They lived on Roosevelt Drive, next door to their grandparents and across the street from the Yale Boathouse.

Both their father and grandfather worked at the Boathouse - an instance of chance and fortune. Decades earlier, during the Depression, their grandparents, Gennaro and Mary Romano, immigrants from Scafati, Naples, would feed the entire neighborhood on his modest salary. Family, Faith, Service, Country, and Football would shape young Jerry.

Jerry distinguished himself at Derby High School both in the classroom and on the playing fields. In 1966, and ’67, the New Haven Register named him to the Football All State. The same time, the Journal Courier selected him to the All-Housatonic League. He capped his football career at Derby High School with an All-American honorable mention. Jerry was often singled out by his coaches during film sessions as a model of consistency and excellence which helped to establish a football tradition in Derby that would endure for decades.

As a scholar-athlete, he was awarded a scholarship at Amherst College and graduated with Honors in 1971. His Honors thesis was titled, The Experience of Robert Lowell’s “Life Studies.” At Amherst, he discovered a passion for American Literature.

Jerry once noted, “It all goes back to Professor Baird. Echoes from the classroom in Johnson Chapel, fleeting images of Baird at work, recurring memories of his style of doing and approaching things. Stuff that somehow works its way into your core. Baird: ‘Yes, yes, yes, but is that what you really believe?’ I think the power of education rests in the lasting influence that a great teacher has upon an individual’s life for decades to follow in ways usually never anticipated, at times only later appreciated.” From Amherst, he applied for a teaching and coaching job at the Taft School, a private boarding secondary school in Watertown, Connecticut. Newly married, the Romanos moved to Watertown for one year but remained for thirty-one. Their three children, Christina, Joyce, and Jerry IV, were born there. Jerry coached football, wrestling, and track, lived on Corridor, and taught English. Subsequently, he became a Class Dean, and was asked to serve as Dean of Students. Jerry would often say, “Honestly, anyone who likes kids should have this good fortune.”

Jerry was granted a sabbatical leave for the 1977-78 academic year. The Romanos lived in their tiny cottage on Cape Cod. It was the year of “The Great Blizzard of ’78”. With their three little children, they watched Henry Beston’s Outermost House float away in the Atlantic.

Jerry commuted to Harvard where he earned a Masters in Education, specifically in Counseling and Consulting Psychology. Through humor and self-deprecation, he would often say that, almost daily, he was reminded by his fellow workers in the Taft Alumni Office, in one subtle way or another, that Harvard somehow erred. When asked in an interview about how he became the director of development, Jerry shared, “How I got to the Alumni Office is another instance of chance and fortune. The former director of development was struck by Cupid and fled, the Headmaster beckoned, and there I remained for 17 years. To travel around the country and have a chance to meet graduates and see the promise in kids I knew at Taft, submerged when I knew them here and now emerging. That is a reward beyond measure. The hard part was that I had to give up teaching and coaching. The good part is that Taft became a stronger school financially - we raised 150 million dollars between 1995 and 2000.”

Summers spent sailing on Pleasant Bay, teaching his children to fish for flounder, dig steamers and quahogs, trapping blue crabs in Muddy Creak as they migrated North from the Chesapeake, retrieving peanut butter sandwiches from the sand, were splendid times and are sustaining memories. As were the road trips to Disney World, in an old brown Chevy station wagon during Taft Spring Break. And later on, attending his children’s and grandchildren’s college graduations.

To his four grandchildren, Kayla, Simone, Tom, and Lily, he was known as Poppy. He was immensely proud of them and would talk about them to anyone who would listen. He followed the oldest granddaughters' careers in Chemistry and Finance with keen interest and curiosity. The most joyful moments for Jerry were seeing his children and grandchildren tucked around the Holiday table for family dinners and celebrations, something his own children enjoyed growing up and driving to Derby, to Nan and Pop’s house for exquisite Sunday feasts.

Jerry loved to travel, and Florence was his favorite destination. But Faicchio, the home of his extended Italian family, was a magnet. In early November, on the hills of the Apennines, he would help with the olive harvest. As the Italian sun bathed his face, he turned to Anne and said, “This is the best job I have ever had.”

A modest man, Jerry was never comfortable being in the limelight. He was honored for his development work and his contribution to the Athletic Tradition of his High School. In 2019, Derby High School inducted him to their Athletic Hall of Fame. With characteristic humility, he credited his great coaches for his successes, as well as the fundraising dream team at Taft.

In his later years, Jerry once wrote, “I am thankful that much has come my way. I am mindful that much has been the doings of others. Last summer, out in Chatham, I was doing what I enjoy a lot. I was out on an island on the bay casting flies to striped bass and looking across the water to the sun rising over the barrier island. It was a time when thoughts make it hard to fish well. Sort of like Thoreau’s ‘It was not beans that I hoed, nor that I hoed beans.’ And back again to Baird’s essay on Thoreau, discovered post-Amherst. And then back again.” A humble man, with a beautiful mind, an enormous capacity for hard work, wicked sense of humor, Jerry led a life where the ordinary transcended to a higher purpose.

Finally, through grit, stubbornness, an indomitable spirit, he endured the most cruel blows: the untimely death of his two brothers, Ralph and Richard, the loss of his daughter, Christina to ovarian cancer, his own debilitating stroke, and his addiction. Family, Nature, and Spirituality sustained him. Nearly 19 years at Alcoholics Anonymous may have been his greatest personal triumph.

Surrounded by his family, Jerry died peacefully in his home in Chatham the afternoon of August 8, 2025. Jerry was predeceased by his brothers, Ralph Romano and Richard Romano, as well as his daughter, Christina E. Holmes. He is survived by his wife, Anne, two children, Joyce A. Romano and Gennaro A. Romano IV, son-in-law, Thomas C. Holmes, four grandchildren, Kayla A. Romano (Anna K. Estep), Simone Romano, Thomas J. Holmes, and Lilliana M. Holmes, various cousins, a large extended family both in the States and in Italy, and many dear friends.

On October 25, 2025 at 11:00 a.m., a Celebration and Thanksgiving Service for the Life of Jerry Romano will be held at St. Christopher’s Episcopal Church, 625 Main Street in Chatham, MA. A reception honoring Jerry’s life and work will be held at The Taft School during Alumni Weekend in May 2026.

In place of flowers, a contribution may be made to the charity of your choice, or to The Romano Scholarship fund at The Taft School. Please visit https://www.taftschool.org/giving/ways-to-give for details.