Charles Jasper Simpson, Jr.

An expert in aviation law and life-long sailor, Charles Jasper Simpson, Jr., died peacefully at his home on Gibson Island, Maryland on July 8, 2026, following a protracted illness. Charlie was born on September 16, 1951, in Washington, D.C., the son of Lt. Col. Charles J. Simpson, USA (Ret.), and Ann Townsend Simpson. During his childhood years, the Simpson family was stationed at various Army posts in the United States (including West Point, NY), Germany, and France.

Charlie graduated from Landon School (1969), and received his B.A., magna cum laude, from Tufts University (1974), and his J.D. from Georgetown University Law Center (1979) where he was lead articles editor of the Law and Politics in International Business. He worked for over forty years at the law firm of Zuckert Scoutt & Rasenberger (now KMA Zuckert), including as managing partner. His practice focused on the international aviation industry, and he advised many foreign airlines and national flag carriers, such as those of Japan, Chile, Turkey, Malaysia, and Pakistan, including in the negotiation and development of open skies air services agreements with the United States. He served as president of the International Aviation Club, on the Board of Directors of the Chilean-American Chamber of Commerce, and on the Board of Trustees of the Washington Lawyers’ Committee for Civil Rights and Urban Affairs.

Charlie took up sailing as a teenager, joining his father at age 16 as weekend crew on board the S&S 47 Foolscap, an ocean-going yawl out of Gibson Island. He was a member of the #1 ranked Tufts University sailing team. Those early steps launched a remarkable competitive career spanning major offshore races on the North American East Coast, the biennial Newport to Bermuda and Transatlantic races, and transatlantic challenges between Newport and Cork, Ireland, and between Bermuda and Bayona, Spain.

As his first foray into “big boat” racing, Charlie joined the crew of the S&S 61 Dora IV, sailing from the Canary Islands to Antigua. From 1973 to 1975, Charlie crewed the Mull 52 La Forza del Destino, racing the Southern Ocean Racing Conference (SORC), Annapolis to Newport, Newport to Bermuda, Newport to Jamaica, Stamford to Vineyard, Marblehead to Halifax, and all the Mackinac races.

In 1975, Charlie joined the crew of the Frers 49 Tenacious, owned by media mogul Ted Turner, to represent Team USA in the 1975 Admiral’s Cup. So impressed was Turner by Charlie’s performance that he offered him a berth on the 12-Meter Courageous in the 1977 America’s Cup, which he declined in order to attend law school.

From 1976–82, Charlie crewed in the SORC, Newport-Bermuda, and Fastnet races on the Derecktor-Kaufmann 64 Boomerang. This included the 1979 Fastnet race, infamous as the deadliest yacht race in history. Boomerang was one of only 85 yachts out of 303 competitors to finish, surviving winds exceeding 60 knots and wave heights exceeding 50 feet.

Away from the water and the office, Charlie was an enthusiastic guitar player who enjoyed playing a tune at holiday parties. A self-professed Beatlemaniac, he collected all of the group’s records and had a substantial library of Beatles-related publications. His favorite song was “While My Guitar Gently Weeps,” written by his hero George Harrison. Charlie will be remembered for his sharp wit, charm, integrity, and steadfast devotion to family and friends. Charlie was never the loudest voice in the room, but when he spoke people listened. Like everything in his life, Charlie battled his illness in his final years with quiet fortitude and grace.

Charlie is survived by his wife Pamela Anne Raymont-Simpson, with whom he shared 48 years of love, laughter, and travels, and by two sons and their spouses—Alexander Townsend Simpson and his wife Carter, and William Charles Raymont Simpson and his wife Margo—and by six grandchildren: Maddie, Rosalie, Jack, Townsend, Charlie, and Stuart, who adored him and called him “Chazzy.” Other survivors include his sister Shreve Simpson and her husband Richard Kagan, and brother-in-law and former crewmate John Raymont and his wife Andria. The family is forever grateful to Charlie’s nurses and caregivers.

A celebration of life is planned for the fall.

In lieu of flowers, contributions may be made to Fund a Fellow for Parkinson's at Georgetown University Medical Center or to the Memorial and Endowment Fund at St. Christopher by the Sea.