Dennis W. Cross – newspaper obituary

Dennis W. Cross (obituary published in The Inquirer and Mirror)

Dennis William Cross, of New York City and Nantucket, died peacefully Friday, April 14, 2023 in Boynton Beach, Fla. His daughters, Louisa and Eliza, were by his bedside through his final days. He was 79.

Dennis had an acute understanding of people. He loved conversation and in getting to know you. Dennis would patiently take the time to understand your perspective and sensibilities. He asked questions and he listened to the answers and he approached problems with humility.

He offered encouragement, he shared his wisdom and he made you feel good about yourself. Dennis also possessed a quick wit and a gift for clever language.

Dennis was a brilliant impersonator and he put this and other skills to use across a range of notorious pranks on his friends and neighbors. In his later years, through a cruel act of nature, Dennis experienced a profound loss of hearing which robbed him of his ability to share conversations, to engage with a world he found fascinating and to appreciate the music which formed one of the key threads of his life.

Dennis was born in Detroit, Mich. in the summer of 1943 to Ralph and Eloise Cross and spent his childhood in the suburb of Grosse Pointe. He was a golf caddy, he played baseball and followed the Detroit Red Wings.

Although he was small in stature, Dennis attained his full height in eighth grade and would chuckle about how he was once the tallest kid.

Dennis was a high achiever. He pressed his father to attend Culver Military Academy in Indiana where he embraced the order and discipline of academy life and rose quickly through the ranks. Dennis didn’t like that society wanted him to wait until adulthood to grant him responsibilities.

He pushed his parents and teachers for his independence and he sought new horizons beyond his Midwestern upbringing. While his parents were away in Germany, Dennis drove from Michigan to Massachusetts and applied in person to Phillips Academy Andover, where much to his satisfaction, they treated adolescents like adults.

At Andover, Dennis found the freedom to make his own choices and it was here that he further developed his love for singing. Dennis auditioned for the school a cappella group and when he was not accepted, he started his own group and named it the Sour Grapes.

After boarding school, Dennis found a larger stage at Yale University where he sang with the Baker’s Dozen. Later, Dennis was tapped to join the Whiffenpoofs: the nation’s oldest and most prestigious collegiate a cappella singing group. At Yale, Dennis formed many of his deepest friendships during his all-night conversations and embraced his love for music and the warmth of song that he shared with friends and family throughout his life.

On his graduation from Yale in 1965, Dennis embarked on a solo trip around the world. He traveled to five continents, forming theories on human nature and seeking cultural exchange.

Dennis would later recount how a fortune teller outside a temple in India had predicted exactly how his life would unfold. On his return, he landed at Suffield Academy in Connecticut where he taught European and Asian history. He then took a sharp turn and with his young wife Anne, moved north to Cambridge to attend Harvard Business School. It was after HBS that Dennis, somewhat reluctantly, joined his family’s machine tool company, working for Cross Europawerk GMBH, the company’s European subsidiary in Stuttgart, Germany.

Dennis and Anne enjoyed their time in Germany, embracing the food, language and most of all the great German composers. But after two years, Dennis was drawn to the excitement of New York City where he joined an investment banking training program at First Boston. As an investment banker in New York, Dennis was fascinated and excited by his work helping governments, hospitals and universities fund their capital projects.

Dennis and Anne raised their daughters Louisa and Eliza and delighted in all of the cultural offerings of the city. Dennis and Anne were devoted to the Canterbury Choral Society where they formed a group of close friends. They enjoyed the museums, concerts and the opera and traversed Central Park, visiting all of the lampposts with a succession of ungovernable dachshunds.

Summers on Nantucket offered time with family, sailing in their Beetle Cat Oyster Cracker, playing tennis, scalloping and enjoying sunset beach picnics. In the winters, Dennis led his family on ski trips to Vermont and the Rockies which provided many laughs recalling harrowing drives through snowy passes, missed flights and the occasional perfect run.

After 25 years as an investment banker, Sarah Lawrence College asked Dennis to join the school as its CFO. In his own words, Dennis recalled that this was the most enjoyable period of his career as he navigated the challenge of being a businessman in the academic world. He attributed his success to being left-handed and his creative approach to solving problems.

In the later years of his professional career, Dennis found a purpose that in many ways would become his life’s work. Dennis was not content to leave his singing behind and created what would become the Yale Whiffenpoof Alumni. The Whiff Alumni rehearsed and performed together to memorialize the most attractive arrangements from a century of song.

Dennis was devoted to these “gentlemen songsters” and with his tireless work, he provided them with a platform to re-live “the good ol’ days.” Together, they assembled along the Eastern Seaboard and beyond, filling clubs, benefits, auditoriums and even the White House with their rich voices, beautiful solos and sometimes bawdy tales of the Harvard- Yale rivalry.

Dennis served as the president of the Yale Whiffenpoof Alumni for 25 years and was widely celebrated for bringing new purpose to Whiffenpoof graduates.

Dennis was a member of the Yale Club, the Nantucket Yacht Club, the Ocean Club of Florida and the Quail Ridge Golf Club. Dennis was a past board member of the Maria Mitchell Association and other nonprofit organizations and several music schools in New York City.

Dennis was predeceased by his wife of 53 years, Anne Frothingham Cross.

He is survived by his brother Ralph Cross and sister Carol Cross; his daughters Louisa Walsh of West Hartford, Conn. and Eliza Miller of Wellesley; and his four granddaughters, Amelia, Peyton, Charlotte and Emerson, all of whom he called “the greatest.”

Dennis will be remembered as a devoted and loving father, a prankster and a gentleman. He was a true friend and was loved by so many. In the words of his friends, Dennis enriched their lives and gave them courage. He had a wonderful voice and a fine appreciation for music from J.S. Bach to Ella Fitzgerald. He was the best living impersonator of Nat King Cole. He was matchless, incomparable and an absolute treasure.

A memorial service to celebrate Dennis’ life will be held at 4 p.m. Saturday, Aug. 5 at the First Congregational Church, 62 Centre St.