Kenneth G. Caldwell passed away peacefully in the company of his loving family on Sunday, October 9, 2016. Born and raised in South Boston, he was a longtime Milton resident. Mr. Caldwell was a graduate of Providence College, received his Masters Degree from Boston State College, and was a member of the U.S. National Guard. He served as the Chief of Staff of the Boston Public Schools until his retirement in 2004. Mr. Caldwell was a member of the Board of Directors of Boston Partners in Education, a former Milton Town Meeting Member, as well as a member of Boston College and Regis College Lifelong Learning Institutes, Providence College Alumni Assn., and a Past Pres. of St. Agatha Holy Name Society. The beloved husband of the late Marilyn Ann (Ranahan) Caldwell, he was the devoted father of Carilyn Rains & her husband, Jay of Sandwich, Marianne Caldwell & her husband, Cyril Moulinie of France, Susan Sousa & her husband, Nuno of Raynham, Amy Tierney & her husband, James of Duxbury, Dennis K. Caldwell of Randolph, and Thomas A. Caldwell & his wife, Amy of Milton. He was also the cherished grandfather of 15 grandchildren & one great granddaughter and dear brother of the late Jay Caldwell of Brockton and Kathleen Gill of Stoughton. A Funeral Mass will be celebrated at St. Agatha Church, Milton, Friday at 10:30 am. Visiting hours at the Alfred D. Thomas Funeral Home, 326 Granite Ave., Milton, Thursday 3 to 8 pm. Burial in Milton Cemetery. In lieu of flowers expressions of sympathy may be made to Massachusetts General Hospital, Cerebral Amyloid Angiopathy Research Lab, 55 Fruit St., Boston, MA 02114.