Leonard Paul Greenlaw

In Loving Memory of Leonard "Lendog" Paul Greenlaw

Lenny "Lendog" Paul Greenlaw, 65, of Winthrop Massachusetts passed away peacefully at his home in Dudley on August 12, 2026. Surrounded by his loving family. Born September 18, 1960, in Winthrop Massachusetts, he spent 13 years living in San Jose California before returning to the town that has always had his heart, Winthrop Massachusetts. Beloved son of Arthur Greenlaw and Patricia Hagen. Lenny is survived by his daughter Julia “Jewels” Greenlaw and son Leonard "Little Lenny" Greenlaw. Along with his partner Deborah Boyd, her two daughters Shelby Hegarty and Heather West of Dudley. As well as extended family and countless friends who loved him like family. If you knew Lenny, you knew everyone called him Lendog. He had a personality that filled every room he walked into, and people naturally wanted to be around. He had no filter, a quick wit, and could make just about anyone laugh. Whether he was cracking jokes, telling stories, singing karaoke, or dancing like nobody was watching, Lendog was always the life of the party. The water was where he was happiest. Being out on his boat with family and friends; music turned all the way up. He had an incredible taste in music and believed every boat ride or get together deserved a great playlist. His belief was spending time with those he loved and great music, made the best memories.

Lendog’s career encompassed many skills. He was a man of many talents. Most recently a truck driver for The Dumpster Divers, Worcester MA, until retiring due to his recent Cancer diagnosis. Other careers include being a maintenance supervisor of nursing homes, a small business owner of "Lenny's Home Repair", and a handy man all around the community; including Beachmont Yatch Club. There wasn't anything he couldn't fix or drive. He has been a member of Winthrop Yatch Club, Elks Yatch Club, Beachmont Yatch Club and more. A longtime member and previous Commodore of Beachmont Yatch Club, Lendog developed lifelong friendships he cherished until the end. The outpouring of love and support he received throughout his illness gave him great comfort.

Upon his diagnosis, doctors called Lendog a “Walking Miracle”. He defied so many odds and close calls. Towards the end, while admitted to UMass ICU, he stated his last wish was to spend his remaining time at home and have a cigarette. And those wishes he did get! Doctors thought he wouldn’t make it 48hrs after discharge. In true Lendog style, he did. He gained a precious month spent with his daughter, Jewels, her paramour, Adam, and his beloved, Debbie. Days before his passing, while just the two of them Lendog said to Adam, “Promise me you will take care of my daughter when I am gone.” Adam promised this. Even nearing the end, he always cared about making sure those he loved were going to be ok after he was gone. Including the love who had his heart, Debbie.

Lendog’s final wish will be honored, that is his ashes be spread off Point Shirley. Deer Island was one of his favorite places since childhood.

Although he is gone, he will never be forgotten. Lendog was and always will be one of a kind. This isn't goodbye, this is see you later. Until we meet again