Willoughby “Bill” Freeland Chesley, Jr., a longtime resident of Stamford, passed away on May 14, 2026, at the age of 68. Bill was predeceased by his parents, Willoughby Freeland Chesley, Sr. and Winifred Hollis Schaefer Chesley.

A Wilton High School graduate in the Class of 1976, Bill also graduated magna cum laude from the University of Bridgeport with a degree in international business. Bill built a career as an entrepreneur and turnaround specialist, dedicating his talents to revitalizing struggling businesses and restoring them to profitability. He thrived on making things work, whether leading a sales team or fixing a product.

Bill found joy in working with both his hands and his mind. He especially enjoyed renovating his home, rebuilding various vehicular engines, and tackling complex mechanical and restoration projects.

His greatest passion, however, was sailing. He spent countless hours on the water, including ocean racing, and took immense pride in his 48-foot yawl, Carillon, custom designed by Sparkman & Stephens.

Bill was not one to give up easily. His unwavering determination was clearly evident in his courageous battle with cancer — he faced life on his own terms, meeting challenges head-on with honesty and resolve.

Bill gave generously of his time to the community. He was a patriot who loved his country, its veterans and our active-duty military. From 1992 through 2009, he was a gracious and welcoming host to the military guests each year at the Fourth of July “Salute our Veterans” celebration in Greenwich, always making them feel honored.

Bill was also an active member of Trinity Church in Greenwich, where he valued both the fellowship and the friendships. This past year, he found great fulfillment participating in Homes for Hope in San Diego. Even in the midst of physical pain, he was the first one up on the roof.

He was a devoted father, brother and friend. All who knew him were touched by his loving heart and steadfast support. He is survived by his beloved daughter Hollis Katherine O’Connor, five siblings and 10 nieces and nephews. He will be remembered for his determination, ingenuity, insight, generosity and an eagerness to help others solve problems and move forward.

A private celebration of life was held June 17, overlooking Larchmont Harbor, a picturesque setting along the northern shore of Long Island Sound.

Bill would be honored by memorial contributions to Trinity Church, 5 River Rd., Cos Cob, CT 06807.