Raymond Joseph Dempsey, Jr. of Canton, MA passed away peacefully on Monday, October 3rd, 2022, surrounded by his loving family. Raymond was born in Winthrop, MA, raised in East Boston, before settling in Canton, MA in 1961. He was a proud graduate of Boston University with a Bachelor of Science degree in Public Relations in 1958. He went on to receive his Master’s degree in Education from Boston State College in 1959, with additional graduate work completed at the College of the Holy Cross, Boston University and Clark University. Mr. Dempsey was a long-standing employee of the Canton Public Schools, teaching mathematics and serving as an Assistant Principal at the William H. Galvin Middle School in Canton, MA from 1961 through to his retirement in 1999. After his retirement, Mr. Dempsey continued to teach algebra in the Canton Summer School Program until 2003 and spent several years as a sales specialist at Macy’s in Braintree, MA. Family was of the utmost importance to Raymond. He especially loved spending Saturday nights with his wife Sophie at his daughters’ homes enjoying family dinners together. Papa absolutely loved attending all his grandchildren’s school and extracurricular activities from baseball and softball games, to dance recitals, band concerts and more over the years. He was very proud to be able to watch his oldest two grandchildren, Nicholas and Juliana, graduate from high school and see them begin their college careers at Bryant University and the College of the Holy Cross. He enjoyed traveling with his wife Sophie to Italy, Alaska, Hawaii, Ireland, Sweden and Norway and many more beautiful places over the years. Most recently, he treasured the special vacations he went on with his wife, daughters, sons-in-law, and his grandchildren. Mr. Dempsey is survived by his devoted wife of sixty-one years, Sophie A. (D’Agostino), his loving daughters Suzanne Dempsey Craig and her husband Christopher R. Craig of Stoughton, MA, Sandra Jean Dempsey Hillcoat and her husband Glen A. Hillcoat of Halifax, MA, and is the proud Papa of his cherished grandchildren Nicholas Raymond Hillcoat, Juliana Sophia Craig, Andrea Suzanne Craig, and Samantha Jean Hillcoat.The beloved son of the late Raymond J. Dempsey and Sophie (Szczechowicz) and brother of Alice M. (Dempsey) Sullivan of Peabody, MA and the late Charles E. Dempsey. Brother-in-law of the late Thomas P. Sullivan and Anthony and Barbara D’Agostino of North Billerica, MA. Devoted uncle of the late Regina E. Sullivan and Michelle DeChristoforo of North Billerica, MA, and Mark D’Agostino. Visiting hours in the Pushard Family Funeral Home, 210 Sherman Street, Canton, Sunday, October 9th, 2022 from 3 p.m. to 6 p.m. Relatives and friends are respectfully invited to attend.. Burial will be private. For directions and on-line guestbook please visit www.roache-pushard.com. In lieu of flowers, gifts may be made to the Dana-Farber Cancer Institute in memory of Raymond J. Dempsey, Jr. to support cancer research and patient care at: Dana-Farber Cancer Institute, P.O. Box 849168, Boston, MA 02284 or via dana-farber.org/gift.
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