Dempsey Wayne Herring Jr, 39, of Waldorf, MD passed away on April 29, 2020 in Brandywine, MD. Dempsey was born in Washington, DC on November 14, 1980 to Dempsey Herring Sr. and Tami Bowling. He was employed as a full-time mechanic in Brandywine, MD and a part-time mechanic in Waldorf, MD. Dempsey ( JR) was described by his family and friends as humble, generous, kind, hardworking, and private. He was a man who wore many hats, and if you knew him, you loved him no matter which one he was wearing at the time. He had a heart of gold and would give you the shirt off his back if you were in need. He cherished spending time with his friends and family the most. He was not dealt an easy path but he overcame most obstacles with grace, patience, persistence, positivity, and a smile. He loved cars and motorcycles; working on them and being around them in general. JR loved all sports, and was a devoted Redskins fan. He passionately played soccer and baseball with friends. He was loved by everyone he met. While he is and will always be dearly missed by those he left behind, we hope he is met with the breeze against his face and an open road where he can truly be free. He is survived by his father, Dempsey Herring Sr of Lexington Park, MD; his mother, Tami Carol Compton-Bowling of Bluefield, WV; daughter, Alyssa Wexler of Franklin, TN; best friend and brother, Joseph Bell of Waldorf, MD; brother, Jeramie Compton of SC; sister, Vicki Carol Bowling of Hughesville, MD; maternal grandmother, Nancy Sue Martz of Princeton, WV; paternal grandmother, Arlene G Walton of Lexington Park, MD; girlfriend Kyrstin Stapleson of Waldorf, MD who is expecting their baby in August; as well as Aunts, Uncles, Cousins and many friends along the east coast. Dempsey will join his paternal grandfather, James Dempsey Walton, at the Queen of Peace Cemetery in St. Mary’s County, Maryland. Due to restrictions presented by COVID-19, a memorial service will be scheduled at a later date.
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