Thomas “Tom” Clinton Matthews Sr., 67, of Chicago’s South Side, passed away on March 25, 2026.

Tom was born on May 3, 1958, in Chicago, IL to the late Charles L. and the late Betty Lou Matthews.  He was a lifelong South Sider who carried his love for Chicago with him in everything he did. Tom is the devoted father to Emily and Tom Jr., and was always a steady, proud presence in their lives. He also shared many years of family life with their mother, Patty. Tom is the beloved brother of William D. (Janice), the late Irene L. Lester, and Charles W. (Tina); and is a dear uncle to many nieces and nephews. He leaves behind many other family members and friends to cherish his memory,

Tom spent much of his career as General Manager at Cullinan’s Stadium Club, where he became a familiar and well-loved figure. He had a natural way of connecting with people, always ready with a story and making everyone feel welcome. He later worked in sales before retiring.

He loved all things sports and was fiercely loyal to his teams: the White Sox, Blackhawks, Bears, Bulls, and Fighting Illini. Whether celebrating or frustrated, he never missed a game and never stopped believing.

He also loved his music and had a gift for storytelling. Tom was generous to a fault and cared deeply about the people in his life. If you were lucky enough to know him, you knew how much he loved his people.

He will be remembered for his warmth, his humor, and the way he made others feel. Tom will be missed dearly by those who knew and loved him.

Cremation is private.  A memorial service will be held at a later date.  Please check back periodically, information will be added once arrangements are finalized.