Joseph "Winks" Elmer Pilkerton
September 11, 1943 ~ May 10, 2026
Joseph “Winks” Elmer Pilkerton, a beloved husband, father, and dedicated community member, passed away on May 10, 2026, at the age of 82. Born on September 11, 1943, in Leonardtown, MD, Joseph lived in California, MD, where he made a lasting impact on those around him.
Joseph graduated from Great Mills High School and dedicated his career to serving as an interior designer for 40 years for Architect of the Capitol. Known for his generosity and warm spirit, he found joy in the simple pleasures of life, such as playing pitch, raising rabbits and chickens, and overseeing the rabbit and chicken stall at the county fair. Joseph was an avid fan of legendary baseball player Jim Palmer, The Baltimore Orioles, NASCAR, Kyle Busch and loved spending weekends at yard sales and auctions in search of unique treasures.
He will also be remembered as a compassionate coach for the Hollywood Swingers women's softball team, where he inspired and nurtured the talents of many young athletes.
Joseph’s friendship with Buddy Joy was a significant part of his life, symbolizing the deep connections he cherished with his companions. His laughter and kindness were felt by everyone who had the privilege of knowing him. He will be deeply missed but fondly remembered for his unwavering spirit, love for family, and commitment to his community.
Winks is survived by his loving wife, Lequita “Tweet” Pilkerton whom he shared 59 loving years with. His son-in-law, Riccardo Pierrotti. He is preceded in death by his daughter Michelle “Shelly” Pilkerton and brother Edward Pilkerton.
The family will receive friends on Wednesday, May 20, 2026, from 9:30 AM to 10:30 AM in the Mattingley-Gardiner Funeral Home, Leonardtown, MD. Where a funeral service will be held at 10:30 AM in the Funeral Home Chapel. Interment will follow in Saint John’s Catholic Cemetery, Hollywood, MD. Serving as pallbearers will be Robbie Tennyson, Sherman Joy, Dale Tarleton, Tyler Ellis, Ronnie Derby, and Mike Derby.
Condolences may be made to the family at www.mgfh.com.
Arrangements provided by the Mattingley-Gardiner Funeral Home and Cremation Services, P.A., Leonardtown, MD.
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Lequita and family, so sorry to hear of your loss. Doug and I enjoyed seeing Joe and you at the County Fair to see the rabbits and chickens. I know that God will wrap his loving arms around you during this difficult time. Waverley Medley