Cleveland Montgomery

In Loving Memory of Cleveland Montgomery

Born in Pritchard, Alabama, on April 12, 1946, Cleveland was the cherished son of Bernice Thomas and Robert Montgomery. He spent much of his childhood under the loving care of his maternal grandmother Rachel Thomas, affectionately known as “Bae”. He was surrounded by the warmth and support of both the Thomas and Montgomery families. Their devout Christian values profoundly shaped Cleveland's character and life journey.

As a young boy, Cleveland delighted in simple pleasures: climbing trees, picking pecans, fishing, and creating unforgettable memories with his cousins and youngest aunt, Charlene. This close-knit and loving environment instilled in him a profound love for family and an appreciation for deep, lifelong friendships.

Cleveland's early education took place within the Mobile County public school system. He graduated from Blount High School, where he was a celebrated baseball player. His love for travel and driving was sparked by his family’s tradition, as elder family members were bus drivers. At the age of 19, Cleveland embarked on his own adventure, moving from Mobile, AL to Washington, DC, with his cousin and roommate, Bennie Montgomery. He was quickly captivated by the vibrancy of ‘Chocolate City’, making it his beloved new home for almost 60 years.

Among his first jobs in the nation’s capital was with a furniture moving and delivery company, routinely delivering to Garfinkel’s jewelry store. During one of these trips, Cleveland’s path crossed with a young elevator operator, Rachel Roundtree, who would become his first wife. Cleveland and Rachel later married and adopted a son, Christopher Montgomery. Encouraged by his father-in-law, Cleveland pursued a career in the federal government, which was known for offering stability and benefits, especially within the Black community in Washington, DC. He began as a driver at Cameron Station in Alexandria, VA, and later ascended to the role of supervisor in the Motor Pool division of the US Department of Transportation (DOT). Highly regarded for his dedication, kindness, and infectious humor, Cleveland was a cherished colleague, always ready with a smile and a good joke.

Cleveland’s journey through life brought him to his second wife, Karen Jackson, during his time at DOT. Married for 16 years, their union was filled with love and companionship until Karen’s passing in 2015.

A lover of life’s many joys, Cleveland was known for his passion for R&B music, his love for dancing, his enjoyment of hearty barbecue and bushels of crabs, and his devotion to football. His generosity and loyalty knew no bounds; he was a faithful friend whose presence was a comforting constant in times of need.

Beloved father, grandfather, brother, and friend, Cleveland passed away peacefully on November 15, 2024. He leaves behind his loving legacy through his children: son, Christopher Montgomery; daughters, Latonya Jackson and Brianna Swain; grandchildren, Joshua Jackson, Donaleigh Forrest, Cornelius Huntley Jr. Kayla Swain-Huntley; brother, Jimmy “Junior” Wilson (Faye); and his beloved aunt, Charlene Colbert. His memory will also be cherished by a host of nieces, nephews, cousins, and dear friends.

Cleveland Montgomery’s life was a testament to the power of love, family, and friendship. His spirit will continue to live on in the hearts of all who were blessed to know him.