Robert Montgomery, 54, of Merigold, MS, departed this life on June 30, 2021 in Mount Pleasant, Wisconsin. He was born on August 15, 1966 to Carrie Louise Harris and Robert Montgomery, Sr.

Robert was educated in Mound Bayou Public Schools and also in New York and Alabama. He is a member of the John F. Kennedy High School class of 1984. He also served in the US Army stationed at Fort Dix, NJ for a short period.

Robert held a Class A CDL license, and drove commercially for 30 years. Some of his best times were spent driving for Greyhound out of the Port Authority in NY and the Washington, DC terminals, and driving various line runs along the East Coast. He also drove for New York City Transit. (NYCMTA) He had previously driven for Central Refrigerated in Salt Lake City, UT, Cal Ark out of Little Rock, AR, and many others over the years, and he and his life partner and business partner, Antoinette co owned Legacy Transportation, LLC and were owner operators leased onto USA Truck in Van Buren, AR.

He passed away in the truck in Wisconsin with Antoinette by his side doing exactly what he loved and had a passion for which was travel and trucking. Together, they had also recently started Legazcie Clothing and Accessories, and were looking forward to buying an RV and retiring from trucking very soon. His dream was to travel with his close friends and family afterwards, and to take his mother to North Carolina and for a trip along the Eastern seaboard, which he often spoke about.

Robert was a gentle giant, and treated everyone he met with generosity and compassion, but especially his mother and Adam, who he truly lived his life for. He was the best son, brother, partner and friend that anyone could ever hope for. He had such an awesome sense of humor, and was the ultimate joker, and just an all around beautiful person!

Robert had a passion for gun collecting, cooking, astronomy and weather, and was a die hard NY Yankees and Alabama Crimson Tide fan, and loved to ride down the road while talking about those things to his special friends who were like brothers, and to whom he had all given special names to. They include Daniel Anderson of Indianola, MS, Derrick “The Heathen” Dolberry of Georgia, Christopher “The Bishop” Pitchford of Jackson, MS, Russell “The Deacon” Walker of Baton Rouge, LA, Marcus “The Nephew” White of Atlanta, GA, Cameron Cooper of Jackson, MS, Sterling Jones of North Carolina, and special surrogate sister Tomika “Mika The New Yorker” Askew of Brooklyn, NY, who were all also truckers and friends of his and Antoinette “First Lady” McIntosh, and who he jokingly called “The Church Of The Diesel Denomination” of which he was known by this small group as “Pastor.”

In addition to his parents, and stepmother Lorraine, Robert leaves to cherish his memory a daughter Chante Montgomery and grandson Isaiah of Amityville, NY, brother Adam Harris of Merigold, MS, sisters Yolanda McKenzie and Juwana Montgomery both of Queens, NY. Also surviving are maternal aunts Geraldine Harris-Hooper, and Dorothy Harris of Memphis, TN, Toni Harris-Doughty (Phillip)of Kansas, Deborah Harris of North Carolina, maternal uncles Larry Nelson and wife of Kansas, Jeffrey Harris of North Carolina, and King Harris, Jr. of New York.

His surviving paternal aunts and uncles include Bentley Heyliger and Jason Heyliger both of Fort Myers, FL, George Heyliger and wife of Syracuse, NY, Bendetta Heyliger of Queens, NY and aunt by marriage, Janice Robinson of North Carolina.

Robert also leaves behind and a host of nieces, nephews, cousins, including his two closest cousins Tracie Moore of California, and Ron Robinson and wife Amber of Springfield, MO as well as a host of special friends with whom he spoke to often while driving including Wanda Solomon of Tacoma, Washington, Tamika Armstrong and special surrogate daughter Sadie Armstrong of Little Rock, AR, Debra Mitchell of New Jersey, and Shafiga Mohamed of Michigan, and surrogate children all over the country.

He and Antoinette named their company LEGACY, and that is what he hoped to and has truly left behind.

A public viewing will be held at Johnson and Scott Mortuary on Friday, July 9th from 5-7pm located at 904 N Chrisman St. Cleveland, MS 38732.

Full services will be held on Saturday, July 10th at 11am at Bethel AME Church at 403 N Edwards, Mound Bayou, MS. There will be no graveside or burial.