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Kenneth Warren Sylvester, Jr.

November 20, 1940 ~ January 18, 2021 (age 80)


Kenneth Warren Sylvester Jr. was born in Bangor, Maine on November 20, 1940 to Pauline and Kenneth Warren Sylvester Sr. He was the oldest of four children. The family soon relocated to the East Deering neighborhood of Portland on Olympia Street. Affectionately known as Kenny Boy to family, the legend of him in that neighborhood and in life began at a young age. He had many stories to tell from those years and many people had stories to tell about him.

At age 18, Kenny Boy began his career as a tractor trailer driver for Americana Transport on Portland’s Waterfront (Commercial Street), hauling seafood all along the east coast. “Trucker Ken” later joined his father as a driver at A & P Food Stores. He enjoyed being on the road. That’s where he was comfortable. He especially loved his trips through the small towns of Downeast Maine. In the mid 1980’s, Trucker Ken took a hiatus from driving and opened a neighborhood bar in East Deering, Sylvester’s Café. It was a popular spot for the local community; however, all were welcome. Ken greeted everyone with his trademark smile. He made people feel welcomed and could get a laugh out of anyone. His sense of humor and storytelling was like no other.  By the mid 1990’s, Trucker Ken resumed his transportation career, working for P & H Transportation hauling 12,000 gallons of propane gas. He was proud to drive that “bomb” and did with such skill and professionalism. In his own words, “I have more miles backing up than you have going forward!” Trucker Ken always said hard work never hurt anyone. He finally retired in 2009 at the age of 69.

Ken was a member of the Teamsters Local 340 Union and the Columbia Social and Athletic Club in East Deering. He loved visiting with his lifelong friends at the “Club” on Sundays. He was a fan of the Boston Red Sox and attended many games through his life. In Ken’s early years, he was a fan of the Washington Redskins football team, then in later years the New England Patriots. He loved to cook the family pasta sauce and meatballs. Ken took pride in making that sauce, and he would tell you so! He would say to his kids, “No one cooks a sauce like your father!”, and he was right.

Another love of “Papa” Ken’s was his family beginning with his six children whom he was so proud of and bragged quite frequently about – Ann Marie Phanor and her husband Jean-Claude, Kenneth W. Sylvester III and his wife Jinlan, Michael A. Sylvester and his wife Diane, Jason P. Sylvester, Gina A. Cupkovic (Weenie) and her husband Aleksandar, and Joseph W. Sylvester (Boo Boo). His eight grandchildren – Valentino Graham, Nicholas Graham, Kenneth Sylvester IV, Gabrielle Sylvester, Mazy Sylvester, Odessa Sylvester, Alex Sim, and Chloe Sylvester. His two great grandchildren – Isabella Graham and Josie Sylvester. He is also survived by one brother, Paul Sylvester and sister-in-law Margaret. Two sisters, Theresa Steeves and brother-in law Charles (Chucky). Carole Millett and brother-in-law Russell, as well as six nieces and one nephew.

Papa Sylvester will be missed dearly by all, but his memory will live on through the stories told and many pictures and videos accumulated over the years of him. In his own words, “I’ve had the best life anyone could have.” We love you Papa. Rest easy.

Following state mandates, and for the safety of all in attendance, face masks are required.

Visiting hours will be held on Thursday, January 21, 2021 from 4-7 pm at A.T. Hutchins Funeral Home, 660 Brighton Avenue, Portland. Private burial in Evergreen Cemetery.

To send flowers to the family or plant a tree in memory of Kenneth Warren Sylvester, Jr., please visit our floral store.


January 21, 2021

4:00 PM to 7:00 PM
A.T. Hutchins Funeral home
660 Brighton Ave
Portland, Maine 04102

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