Leonard Matthew Smith.

Leonard Matthew Smith, born on January 21, 1957, in Chicago, Illinois, departed this world on September 15, 2026, after a courageous battle with cancer. Leonard’s journey was marked by resilience, love, and an unwavering commitment to his family and friends. Leonard was raised by his beloved parents, Mack Smith and Mattie Orum Smith, both of whom preceded him in death, along with his dear brothers, Willie Collins, Mack Lenard Smith, and Donnelly Smith. The Smith family was a close-knit one, and Leonard cherished every moment spent with his siblings. Though Leonard's formal education concluded in the eighth grade, he possessed a natural entrepreneurial spirit, becoming a self-made boss and hustler who inspired many with his determination and drive. Leonard's work ethic was unparalleled, as was his commitment to those he loved. Leonard was a man of many passions; he loved shooting pool, playing gambling games, and rolling dice. He was never happier than when surrounded by his cherished family, friends, and his loyal dog. With a penchant for dancing and a love of humor, Leonard was truly the life of the party. His ability to bring joy and laughter to those around him was a testament to his generous spirit and warm heart. Leonard leaves behind a loving family who will forever hold him in their hearts. He is survived by his devoted daughters, Loise and Joandrea, and his son, Javon. His sisters, Dora Jean, Marvella, Mattie Darlene, and Crystal, along with his brothers, Booker J and Barry Joe, will miss him dearly. Leonard was also a proud grandfather to 11 grandchildren and a great-grandfather to two great-grandchildren. Though Leonard experienced a divorce, he found a true and loving relationship with Jewel Smith, who brought him joy in his later years. His family and friends were the cornerstones of his life, and he was endlessly grateful for their love and support. A service to celebrate Leonard's life will be held on October 2, 2026, at 12:00 PM at the Northwest Funeral Home, located at 6630 W Hampton Ave, Milwaukee, WI. In lieu of flowers, the family kindly requests that donations be made to a charity of your choice in Leonard’s memory. In a special message from Leonard, he wished to express his heartfelt gratitude: "Leonard would like to let you all know that he appreciates and thanks you all for the love, caring, understanding, and just being there for him during the good times and bad times. He loves you all." Leonard Matthew Smith will be remembered as a loving father, brother, grandfather, and friend. His spirit will live on in the hearts of all who were privileged to know him. May he rest in peace.