Willoughby Freeland Chesley Jr.

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

He graduated magna cum laude from the University of Bridgeport with a degree in International Business, and 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 automobile 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 and was a devoted member of Trinity Church in Greenwich. This past year, he found great fulfillment participating in Homes for Hope in San Diego, where (despite his physical pain) he helped build a home for a family in need.

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 ten nieces and nephews. He will be remembered for his determination, ingenuity, insight, generosity, and eagerness to help others solve problems and move forward.

Extended family and friends are kindly asked to contact a family member for details of the June 17th memorial. In lieu of flowers, memorial contributions may be made to Trinity Church, 5 River Road, Cos Cob, CT 06807.