William Young Naylor Jr.

It is with profound sadness that we announce the passing of William Young Naylor Jr., affectionately known as Billy, on May 15, 2026. Billy passed away peacefully and comfortably at Tufts Medical Center in Boston, Massachusetts, at the age of 65. Born on July 6, 1960, in Warwick, Rhode Island, Billy lived a vibrant and fulfilling life, leaving an indelible mark on all who knew him. Billy was the beloved son of the late William Y. Naylor Sr. and Gloria J. Naylor, who predeceased him. He is survived by his devoted wife of over 42 years, Eileen Naylor, whom he married on July 13, 1985. Together, they built a life full of love and laughter, raising four cherished children: Jennifer L. Asencio, Jessica R. Naylor, Cara Young, and William Y. Naylor III, who, along with his wife Sydney M. Naylor, carry forward Billy’s legacy. Billy’s pride and joy were his grandchildren—Alyaah, Dorsy, Daniel, Damon, Matthew, and Jakob—and his great-granddaughter, Dezmarie. His loving sisters, Colleen Woodbine and Cynthia Woodbine, also survive him, along with a wide circle of extended family and friends who were touched by his kindness and humor. Billy served his country with honor in the U.S. Army from 1977, a testament to his dedication and commitment to others. Following his service, he embarked on a career as a RIPTA bus driver, a role he fulfilled with dedication and pride for 22 years until his retirement in 2014. His work was more than just a job; it was a way to connect with the community he loved so dearly. A man of many interests, Billy was a true adventurer, having traveled to over 30 countries, each journey adding a rich tapestry of experiences to his life. He was a passionate Harley Davidson enthusiast, known for the joy he found in the open road. At home, he delighted in cooking for friends and family, turning every meal into a celebration. His leisure time was often spent by his pool, in the comfort of his own backyard, or in the companionship of his beloved pets, Cinnamon the cat and later, Jackson the dog. Billy was a proud member of the American Transportation Union and the Warwick Sportsman's Association. His involvement in these communities brought him not only camaraderie but also the opportunity to uplift those around him with his infectious spirit. Known for his ability to turn any function into a party, Billy was truly the light of any room he entered. His wit and humor were matched only by his compassion and sincerity, qualities that endeared him to everyone he met. In lieu of flowers, the family kindly requests that donations be made to The HeartBrothers Foundation, an organization close to Billy's heart, at https://www.heartbrothers.org. The Naylor family extends their heartfelt gratitude to the dedicated doctors and nurses at Tufts Medical Center for the compassionate care and support they provided Billy in his final months. Their unwavering dedication and kindness brought comfort and peace to Billy and his loved ones. As we say goodbye to Billy, let us remember the joy and laughter he brought into our lives. His warmth, humor, and love will continue to guide and inspire us. He leaves behind a legacy of love, service, and adventure—a testament to a life well-lived. Rest in peace, dear Billy. You will be deeply missed and fondly remembered by all who had the privilege of knowing you.