Henry “Harry” Hill Anderson Jr. served on the Tall Ships America board for years. He was inducted into the National Sailing Hall of Fame. The New York Times once called him the “M.V.P. of American Sailing.” And all of that is true, and all of it mattered. But the people who knew him best don’t tend to lead with his résumé.
They lead with something harder to quantify — the way he made you feel like the work you were doing mattered. The way he showed up, genuinely, for our community over decades. Not because he had to. Because he believed in it. Because he believed in you.
He brought that same devotion home. Harry was as dedicated to his family as he was to the sea. Those weren’t separate lives. That was one life, lived with extraordinary wholeness — full presence, full commitment, full love.
June 2nd marks Harry’s birthday and is a day we recognize each year, because some people leave a mark that doesn’t fade with time. Harry was one of those people.
If he touched your life — if you sailed with him, worked alongside him, or simply found yourself in a conversation you’ve never quite forgotten — we want to hear from you. Please share your story with us at Impact@tallshipsamerica.org.
THE STORIES:
Despite having chosen paths in life that had no overlap with sailing, Harry found ways to be a part of our lives. For me, it was my 40-plus-year career in the field of historic preservation. Not only did he ask my advice about his house on Spring Street, he would also send me home with a tool or moulding to repair or duplicate. After my father died at 69, he reached out to my brothers and me, letting us know that he was there for us, almost certainly remembering his sense of loss and aloneness at losing his father prematurely. His gesture and the relationship that developed between us (Jodee and our children, too) in the years following will never be forgotten
-Townsend Anderson
It is difficult to fully convey in words the profound impact Harry had on my life. In many ways, my career path, personal outlook, and even much of my social circle would have been entirely different had I never met Harry. From my teenage years until his passing nearly two decades later, he was not only a mentor, but also a trusted friend whose guidance and wisdom shaped some of the most important years of my life.
Every moment spent with Harry became a cherished memory. Whether enjoying cocktails at the Reading Room, dinners at Harbour Court, or cruising through the waters of Cape Breton Island aboard the M/V Annie B., time with him was always filled with laughter, remarkable stories, and invaluable lessons. Harry possessed a rare wit, effortless sense of humor, and an extraordinary breadth of life experience that made him one of the most fascinating individuals I have ever known.
Despite his stature and influence in the world of yachting, Harry carried himself with quiet humility and the understated grace of a true gentleman. There is scarcely a week that passes that I do not reflect upon something he taught me. I will forever remain grateful for his friendship, mentorship, and example.
-Caleb M. Pifer
I had the pleasure of meeting Harry my sophomore year of college (1982) at the University of Rhode Island. I was on the Sailing Team and was introduced to Harry, along with my Sailing Team Co-Captain, Peter Cusick by a couple of senior statesmen on our team, Jamie Hilton and Dave Price who had developed a friendship with Harry by racing on his New York 40 sailboat. URI Sailing was in the process of moving our team closer to home at the Salt Pond in Narragansett and we were fund raising to purchase the materials needed to buy a 60′ floating dock for our team boats. Pete and I asked Harry for a lunch meeting at Clarke Cookhouse in Newport to present our plan in hope of gaining Harry’s support. We dressed up in our blue blazers, had a great lunch with Harry, discussed our team ambitions, and had a great time chatting about Harry’s time spent on the America’s Cup Selection Committee. Harry was a storied yachting celebrity to us. After lunch Harry asked us to submit our plans for the dock, which we did on the spot, complete with a detailed blueprint and estimate of materials and costs.
The next week Harry sent us a check for $10,000, of the many gifts Harry would give to our (Club Sport funded team), over the next 40 years. Harry loved our team’s enthusiasm and commitment. And he loved helping kids get out on the water! I will always cherish our friendship with Harry!
-John Lombard
Little Red Bug”, used for transportation around the grounds of the Jekyll Island Club, the revival of which was one of many “projects” that Harry participated in or spearheaded in his later years, and through which he connected me to people with whom I would collaborate in one way or another. Christine and Jodee, wives of brother Hank and me respectively, visited Harry on Jekyll Island several years running. So taken with their devotion, he would introduce them as his nieces at the Club bar where he took his daily The Famous Grouse scotch whiskeys. Harry was the family historian, as well as an accomplished “amateur historian”. So prolific were his logs and research papers, meticulously compiled, edited, and mailed (later emailed) to family and friends.
-Townsend Anderson
This framed photograph of Harry with President and Mamie Eisenhower observing the 1958 America’s Cup (below right) arrived at Christmastime. Harry and his mother (“Granny”) would alternate Christmases between his brothers’ David and Walter “Jim” Anderson families. It made a huge impression on this seven-year-old nephew. The photo was displayed on one of the fireplace mantels for years. Harry would give the family a photo every Christmas, usually a professional photo of one of his boats under sail with him at the helm (e.g., Taniwa).
-Townsend Anderson
One of the most memorable men I’ve ever known! In the early 1990’s Elizabeth Meyer and a group of us founded IYRS. And one of the first members of our board was Harry. We all either know Elizabeth or knew of her. She always deferred to Harry when Harry spoke – he always spoke so well with total common sense. He was beloved by all of us at International Yacht Restoration School.
-John Johnson
As the notes below attest, Harry enjoyed a long friendship with Prince Phillip. Harry never boasted to us about any of his worldwide connections and friendships. We more often than not learned about them through third parties. I still don’t know, but would love to learn about, what I have only read as the secretive Imperial Poona Yacht Club. We do, however, proudly note, as Prince Phillip quips above, that Harry was the last Commodore of the NYYC to successfully defend the America’s Cup! Commodore David Elwell, another skiing, not yachting connection, used to joke with me about how Harry would wiggle his nose at the mention of the technology-driven transformation of America’s Cup contender design.
-Townsend Anderson
His whole life was been dedicated to promoting and improving the sport of sailing. While he was in law school he worked closely with Harold Vanderbilt on writing the Racing Rules of Sailing. Harry said, “NAYRU (North American Yacht Racing Union) was really founded to do two things: To develop the racing rules, and create handicap ratings. After World War II, we got the rules confirmed internationally and domestically, but we are still battling to find the best handicap rating rule.
-Craig Leweck
