Leo Roosevelt Cherry Sr. Obituary - Visitation & Funeral Information

Obituary of Leo R. Cherry, Sr. Leo Roosevelt Cherry, Sr. 80, born December 27,1941, twin #2 in Salisbury, Maryland to the late Preston and Amanda Cherry of Berlin, Maryland, peacefully departed this life in his home on Sunday, May 15, 2022. He was educated in the public schools of Worcester County, Maryland. His Christian journey began at St. John’s United Methodist Church in Sinepuxent (Berlin) Maryland, where his great grandmother was one of the founders. During his teenage years, he joined Mt. Zion Baptist Church in Snow Hill, with his father, later joining St. James AME Zion Church in Salisbury, MD under the leadership of the Rev. Charles Mack, maintaining his membership until his death under the leadership of the Rev. David McClendon. Leo enjoyed working on the farm with his family and huckstering in Ocean City with his father. Building upon the skills of farming that his father instilled in him, he started farming himself. With the proceeds from this, and various odd jobs working around the community, he bought his very first car, a black Ford that he was especially proud of, as well as a Harley- Davidson motorcycle, of which he would boast about often. After moving to Salisbury he worked several jobs, driving truck, working for several tire companies in Salisbury area and other jobs. Leo was proud of being able to accomplish so many things at his age, as well as maintaining his house on East Road, which he shared with two friends, Flora, and Goode. Leo was enlisted into United States Army 1967, stationed in Korea as a mechanic servicing the large trucks and other duties. He was also proud of being promoted to Sargent in the short time that he was there. Leo was very proud of being a Korean veteran, as he often talked about in his many stories. After returning home he joined Wicomico Memorial VFW Post 10159 and held several offices; he was proud of being one of the original members of the Marching Unit (honor guard), proudly marching in parades representing the VFW, and becoming a Life Member. He was also a Charter member of Military order of The Cootie, Sho Crabers, Cootie #5. He worked at Open Roads, Chris Craft, E.D. Lighting, Con Diesel (where he learned the trade of welding, of which he was especially proud of, and would speak of often to anyone who would listen) and was a truck driver for several companies. Later, utilizing the skills and love of cooking that he learned from his mother and aunts, he maintained the Leo Cherry and Sons mobile catering business, becoming well-known for his familiar catering van, a proprietary BBQ sauce used in is food, and gaining the rightly earned nickname of “The Goat Man”. Eventually, he would work with the Board of Education of Wicomico County until ailments made it necessary for his retirement. His numerous hobbies and pastimes consisted of drawing, collecting art and antiquing. Leo enjoyed driving and owned many cars and motorcycle which he loved and often reminisced about. An avid collector of various and sundry items, he would take great pains to find or make use of things other people couldn’t. He also enjoyed watching antique and classic car and collectable shows on television; he was particularly pleased when one of his own pieces he owned was showcased on CHESAPEAKE COLLECTABLE on MPT. As a “Jack of all trades” he mastered a number of fascinating traits. After returning home from the service, he met and married Shirley Ellen Handy, and from that union twin boys were born. After the death of his wife, he later met and fell in love with Helen Turner Nichols, married and had enjoyed many years together, traveling, collecting African-American memorabilia, attending local auctions, and being very active with Military Order of the Cootie and the Tomb Trek Committee, placing wreaths at grave of Unknowns and other Veterans and attended the VFW and Military Order of the Cootie Conventions. He leaves to cherish his loving memory his wife Helen Cherry, their blended family of children, twin boys Leo and Preston Cherry, Fonnette (James) Simpson, Cindy Palmer, Howard (Tina) Nichols, Leroy (Betty) Nichols, Kewin (Sheela) Nichols; five sisters Maria Carter, Regina Jackson, Amanda Mitchell, Sally Cherry, and Sheila Cherry; one brother-in-law, Harold (Lorraine) Turner, sister-in laws: Addie Purnell, Geri Gober, Charolette Polk, Dolly (JP) Reaves, and Lucy (Bill) Thompson. He also leaves a host of nieces and nephews with special mention to Inez, Ronalda, Frank, and Harris Jr. (Sonny), as well as a number of god children, including Rhonda Turner, Amanda, Danielle, and D.J. and his namesake, Leo, a large village of family, church family and friends. Proceeding him in death were his parents, Preston, and Amanda Cherry, two brothers Harris Purnell and Dempster Cherry, two cousins raised as brothers Theodore and William Cherry, one sister-in-law Rosalee Williams, brothers-in-law: James Mitchell, Donald Carter, Warner Jr., George, Richard, John Turner, Samuel Williams, and many other loving family members. He lived his life as if no man were a stranger; they would eventually be a friend or part of the family. He had a story for everything and made everything and made every opportunity to share it. He will be sorely missed… Lovingly Submitted, The Family

Leo Roosevelt Cherry Sr.

December 27, 1941 - May 15, 2022