James R. “Bob” Willing, age 89, a lifelong resident of Winchester, passed away on July 24th, lovingly surrounded by his family. He was the beloved husband of the late Sarane “Sally” Willing.
Born and raised in Winchester, MA, Bob was the son of the late James Burland Willing and Marion Smith Willing. He was educated in Winchester and earned his bachelor's degree from Dartmouth College. He served in the National Guard and then enjoyed a very successful career of over 60 years in finance as an Investment Advisor in Wealth Management. However, Bob was so much more than a successful businessman. He was an amazing family man, friend, teacher, coach, mentor and role model. He truly loved people and would do anything to help anyone.
Bob married the love of his life, Sally, in 1960, and raised their 3 children in Winchester. Bob was an active participant in the Winchester community supporting his children along with their friends and families in all of their endeavors. He was also deeply involved as a long-time member of numerous organizations around town including the following: Winchester Savings Bank - Trustee for 55 years; Winchester Hospital - Trustee and member of the Board of Investments; Winchester Mount Vernon House - Trustee and member of the Finance Committee; The Mary E. Murphy and John F. Murphy, Jr. Charitable Trust - Trustee; Winchester Country Club - Board of Directors and past Chairman of the Membership & Greens Committees; The Jenks Center - Board member; The Griffin Museum of Photography - Board member; and The Parish of the Epiphany - Lifelong member.
Bob was also a proud member of the Rockport Golf Club, the Bay State Seniors Golf Association, and the National Association of Watch and Clock Collectors.
A diehard Patriots and Boston sports fan, Bob not only loved watching, but also enjoyed playing sports over the years such as baseball, golf, tennis, and curling. In addition, he had many hobbies including his love of antique cars and clocks. He was a musician and talented piano, saxophone, and accordion player. Bob loved to join in on family ping pong games, horseshoe matches, corn-hole tournaments and card games. He was a member of the Dartmouth College Glee Club where he had the privilege of singing on both the Ed Sullivan and Perry Como Shows. Bob was quite a handyman and skilled builder who renovated many homes and built a two-story club house equipped with a hidden trap door, fireman’s pole, and slide for his children and grandchildren.
Bob’s world revolved around his family and pets. He was a wonderful husband, father, grandfather (Grampy), great grandfather and uncle. The extended family enjoyed spending summers together in Rockport and vacationing in Florida and Bermuda. Bob positively influenced everyone he knew, and his legacy will live on through his devoted family.
Bob is survived by his children: Debbie Carson and her husband, Dan of Winchester, Patsy Macaluso and her husband, John of Reading, and daughter-in-law, Kelly Willing of Reading. He was pre-deceased by a son, Jim Willing. He was the beloved grandfather of Bobby and Olivia Carson, Kevin and Erica Carson, Brett and Jessica Macaluso, Scottie and Shannon Carson, Cody and Lexi Macaluso, Tori Carson and Billy Poirier and Haley Macaluso; great grandfather of Carter, Ellie and Charlotte Carson and Gracelyn Macaluso. He was the dear brother of the late Patsy Willing MacDowell, and is further survived by many nieces, nephews, grandnieces, grandnephews, cousins, and friends. A dog lover, Bob owned several furry friends over the years and leaves behind his adored Bichon Frise, “Pandy”.
A Memorial Service will be held at the Parish of the Epiphany, 70 Church St., Winchester, on Tuesday, August 5th at 11:00 a.m. Relatives and friends are kindly invited to attend. Interment is private.
In lieu of flowers, donations in Bob’s memory may be made to Winchester Hospital at Beth Israel Lahey Health Winchester Hospital, Office of Philanthropy, 529 Main St., 4th Floor, Charlestown, MA 02129 or at https://giving.bilh.org or to the MSPCA at Northeast Animal Shelter, 347 Highland Ave., Salem, MA 01970 or at https://mspca.org.