Ricky Dejuan McCaskill, Sr. was born March 3, 1964, in Winston-Salem, NC.

Ricky was raised in the Happy Hill Gardens community of Winston Salem.  He graduated from Parkland High School and later attended Fayetteville State University. Later in life he decided to return to school and attended Winston Salem State and took several courses.

He most recently worked for the City of Winston-Salem for several years.  He loved sports, especially the Washington Commanders football team. He was an awesome athlete and he loved to coach kids who played football.  He constantly mentored his siblings Sean and Cayman Smith and would always give them feedback to help them improve in sports.  He was the oldest amongst his siblings and always had a tight bond with his family.  He also had a special connection with his cousin, Brenda Teal Simon, who stayed committed to helping him when he became ill. He had a devoted partner in Veronica Clark, she and her family were instrumental in providing care for him when he needed it most.

He also had special relationships with sisters, Dakeeta Hunter and Porsche Smith; his cousins, Douglas Lindsay, Tameka Bernard (Chris), Chad Waiters, and Kendra Windham (Alex) and always tried to provide them with guidance and protection, he was known as "Big Cuz."  He adored his maternal aunts, Margaretta McCaskill and Angelon Watson (deceased) and they constantly reminded him of how they spoiled him over the years.

Ricky was a jokester and loved to laugh, have fun and tease others, especially about sports.  He made a friend wherever he went, everyone knew "Rick."  He continued to maintain relationships with several of his childhood friends. He was very proud of his children and loved being a grandfather.  He also served as a father figure to several young men in the community.

He was preceded in death by his mother, Jeanette M. McCaskill; grandmother, Diane McCaskill McNeill; and aunt, Angelon McCaskill Watson.

He is survived by his father, Harold L. Smith; grandfathers, Herbert McCummings and Charles McNeill; his sisters, Dakeeta McCaskill Hunter (Marvin), China King-McCaskill, Lisa Smith, Tamiko Burvick, Porcshe Smith and Jada Smith; his brothers, Kelvin McCaskill, Melvin McCaskill (Shaunasia), Richard Smith, Tshombe Smith, Sean Smith, Cayman Smith; step-brother, Weymouth Jones (Rose); his children, Chaverria Wilson and Ricky McCaskill Jr.; and his 4 grandchildren, Amaryanna Wilson, Jezariah Austin, Jahmai Austin and Naeem Jackson;  and a host of aunts, uncles, nieces, nephews, cousins and dear friends.

Memorial services will be held at 1:00pm Saturday, October 8, 2022 at the Russell Funeral Home Chapel.