Matthew S. Webb

1984 – 2026

Matthew S. Webb, 41, of Olive Hill, passed away on January 6, 2026. Born on August 16, 1984, in Carlisle, Kentucky, he was the son of Donnie and Tiawatha Webb.

His passion for breaking things and then getting overly pissed off while fixing them began early in life and became his lifelong passion. In 2024, he achieved a dream milestone by obtaining his LLC and opening his own garage. While he loved working on vehicles, he got more entertainment and joy from trying to teach others. Either somewhat patiently trying to teach his wife the tools of the trade, or planning to pass his skills on to his son, the garage became more than a workplace, it was a place of connection, love, and colorful language.

In late 2024, Matt followed his heart back to his hometown of Olive Hill, particularly back to Soldier. There, he become his authentic self again, he smiled bigger, laughed louder, and loved more genuinely. Matt loved pushing the boundaries just far enough to have fun without getting himself in to much trouble, he utilized the loyalty and bonds with the family he made while at home. He reconnected with old friends, and built new bonds. He brought people together, he could bring anyone together.

While many mourn the loss of a great friend, Matthew was so much more than that. He was the rock for two of his favorite people, a master of sarcastic humor and impeccable bad timing, and even a glorious pain in the ass to a select few. Yet, no matter what happened in life, once someone became important to him, once they were family, he would always show up when needed. There was so much more to him than just a man; he was a father, a friend, a best friend, and so much more. 

Matthew is survived by a wife Dezaray Webb, a girlfriend Dianna Martin both of Olive Hill a daughter Isabella August Webb; and son Matthew Stacy Webb Jr, and Elijah Riley who he loved like his own. He also leaves behind a family built from years of loyalty and genuine love, Rick Oliver, Tom Carroll, Jessica Riley, Sadie Coppage, some very important Skaggs Jameson,Tatter, Jeffrey, and Nathan, Jared Harris and many more.  Matt never quit caring about anyone he considered family even if they didn't always see eye to eye, he leaves behind life long friends Willie Greenhill, Jason Bayes, Matt Grubb. Uncle Matt leaves behind nieces and nephews Thomas Allen, Cara Faye, Jasper Jay, and Bentley Cage.

He was preceded in death by his daughter, Gabriella Nevaeh Webb. 

Service dates and times are currently being determined and will be announced at a future date.

“Family are the people who still love you at rock bottom, stand and fight beside you even if your wrong, the ones who don't hesitate to help when everything is messed up. Those who know your past, who see the bad parts of you, the darkness and pain, but still love you, those are the people who are your family. Blood doesn't make you Family, Love does ” - Matthew Stacy Webb

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