Dennis J. Drain

March 29, 1955 - March 15, 2023

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Obituary for Dennis J. Drain

Dennis Jeffrey Drain, 67, passed away peacefully at his home on Wednesday, March 15th, 2023 surrounded by his loving family. Dennis, the devoted husband and family man, is survived by his wife of 43 years, Sheila; his sister Debbie Drain Hughes (Paul); his three sons Sean, Joseph (Elitza), and Stephen (Katie); and his granddog, Rudy. Dennis was predeceased by his parents, Hellen and Donald, and his two brothers, Donald and David. After growing up in the Milton Youth Hockey system, Dennis went on to play hockey for Stonehill College (class of 79), but returned to his roots to spend 38 years coaching and volunteering for Milton Youth Hockey. Not only did Dennis coach for the town soccer, baseball, and hockey programs for the better part of a decade, Dennis also volunteered at Milton’s Learn to Skate program from 1984 to 2022 before a cancer diagnosis left him on the sidelines this past winter. Dennis worked in finance, as an accountant to many small businesses for over 40 years and later earned the title of CFO for Lantell Telecommunications. Outside of his professional life, he loved to play hockey and soccer, he loved his weekend warrior projects, but most important to him, he loved spending time with his family. Dennis Drain was the consummate family man, a tremendous role model, a loving husband, an exceptional father, a supportive brother, and one of the nicest people anybody knew. Visitation will be held at the Dolan Funeral Home, 460 Granite Avenue, MILTON on Tuesday, March 21st. from 9 - 11AM. Funeral service to begin at 11:30AM at Saint Elizabeth Church. Interment Private. Relatives and friends invited. In lieu of flowers, we kindly ask that you consider making a small donation to Milton Youth Hockey (with “Learn to Skate” in the memo line), a cause that was close to Dennis’s heart. Your contribution will help honor Dennis’s memory and make a positive impact on others. Donations can be sent to: Milton Youth Hockey 377 Willard St, #416 Quincy, MA 02169

Services

21 Mar

Visiting Hours

09:00 AM - 11:00 AM

Dolan Funeral Homes and Cremation Services - EAST MILTON SQUARE 460 Granite Avenue Milton, MA 02186 Get Directions »
21 Mar

Funeral Mass

11:30 AM - 12:30 PM

Our Lady of the Visitation Parish (Saint Elizabeth Church) 350 Reedsdale Road Milton, MA 02186 Get Directions »
by Obituary Assistant

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Condolences

  • April 04, 2023

    I am so sorry to hear of Dennis's passing. We played a lot of hockey during our school years. Dennis was a very kind person. Shared a lot of car rides back and forth to rinks around Milton. My best to his family.

  • March 23, 2023

    I was so very to hear of Dennis' passing. I met him over 40 years ago, he did my taxes. And over the years he continued to do my mothers taxes and when she was no longer able to go to Dennis he came to her house every year. Dennis was the nicest, nicest guy. Fun to talk with over hockey, a great sense of humor and he was so proud of his family. If there were more people like Dennis the world would be a happier place. I am sure he has found a good hockey and soccer team up in heaven. Deb McDougall

  • March 23, 2023

    Dear Sheila and Boys, We were all so sad when we heard of Dennis' passing. We remember him and all of you on Willoughby....always playing some sport in the yard or on the street. Life was so different then. Our prayers and sympathy are with all of you at this sad time. Sincerely, Bill and Alice Mercer

  • March 21, 2023

    Dennis was indeed the consummate family man. He was always working outdoors with Sheila making their home sun a beautiful and welcoming place. Their children are success stories, and Dennis had a direct hand in being a loving role model and father. Dennis and Sheila had a vibrant, authentic, bond; a lifelong love affair. We mourn with you. -- Suzette and David Standring

  • March 21, 2023

    To the Drains May your memories keep you strong in the future. Dennis fought a hard battle with the support of his family. He will always be with you in your hearts. Sincerely Helen Bartoloni

  • March 20, 2023

    We are so deeply saddened with Dennis' passing. Having known him for 24 years, we were honored to call him a true family friend. He was the kindest most peaceful man with a hearty laugh and full of life. We mourn in your loss and will forever remember him. Wishing you each comfort in knowing how wonderful he was. Love, The Powers & McAdams families

  • March 20, 2023

    Deepest sympathies to the Drain family Dennis was a friend and a true gentleman,it was a pleasure to have known him Paul Leone and family

  • March 18, 2023

    Deepest sympathy to the Drain Family from Mike ,Walter and the staff at the Hillside Pub

  • March 18, 2023

    Dear Sheila, sons and family, Our sincere condolences on the passing of Dennis. He was a true family man. He also helped so many kids through his coaching. Love to all of you. Karen & Larry McEachern

  • March 18, 2023

    Sending prayers to Sheila and your family.

  • March 17, 2023

    Condolences to the Drain family. I will always remember that, during the years we worked together, whenever Sheila talked about her husband and family, it was always with a smile on her face. I'm sure it was a reflection of Dennis' wonderful attitude and the fact he was a great dad and husband. So very sorry for your loss.

  • March 17, 2023

    My brother Tom and I played hockey, and coached in Milton with Dennis, for many many years. He was a real "townie". We really got to know and appreciate the kind person that he was. Way back when I was a single guy, and Dennis and I were coaching together, one year he invited me to the Drain home for Christmas Eve with his family. I will never forget that. That was Dennis. I tried to describe him today to somebody and the first word to come to mind was "passionate". He used to talk about his kids, and them playing hockey, and his eyes would well up with tears. Dennis left his mark on the world and he will be missed. My prayers to the entire Drain family. Boys....keep your chins up and be proud of him. May he rest in peace.

  • March 17, 2023

    Our deepest sympathy to Shiela, Sean, Joe, and Stephan on the very sad passing of your lovely husband and Dad Dennis R I P. Rita and I met him in November outside Maureen n Joe's house with you Sean and the soft top car he was a gentleman,may his gentle soul rest in peace from the Shine family Ireland

  • March 17, 2023

    So sorry for your loss. I have fond memories of living next door to you all on Willoughby Rd. Sending you all strength and peace during this difficult time. Carrie

  • March 17, 2023

    To the Drain family, Thoughts and prayers go out to all of you. Dennis was one of the best a very proud man and dedicated to those he loved respecting everyone. His strength and sense of humor will be missed, and you now have your own guardian angel watching over each and every one of you.