Olivia James Cherry was born on October 18, 1926 in Hampton, Virginia to the late Wilson James Sr. and Lucille James Bowman. Olivia was the wife of Linear Clyde Cherry Jr. and the mother of Linette C. Hunter, Kevin Harris, and Linear C. Cherry III.

Olivia was a graduate of the class of 1946 from George P. Phenix High School in the Hampton Public School System. She graduated from Cortex Business School in Washington, D.C., after continuing her education, and was the first Black American to be hired by Macy's Department Store in 1950 in New York City. After working in the Macy's accounting department, Olivia began working with the Army Corps of Engineers in New York. She came to Chesapeake, Virginia in 1973 to work as a secretary for the Norfolk Public School System's Special Needs Department. After years of dedicated work, Olivia retired from Norfolk Social Services.

Olivia was a faithful and steadfast member of St. Thomas AME Zion Church in Norfolk, Virginia. She was a member of the choir for 40 years and taught Sunday School for 20 years. Olivia was a member of the Willing Workers and was involved in other church ministries. She was also a member of the Order of the of Eastern Star, Dorcas Bethany Bessie Ellison Chapter 50.

Olivia was a true people-person. She loved being around her loved ones, meeting new friends, talking with others, and caring for them. She also loved to travel. She was most proud using her computer skills to send cards and messages to her friends and family, showing her love and appreciation. She never missed a family member's birthday or holidays, and consistently sent everyone cards or special messages. Olivia was responsible for family keepsakes. She was camera ready, fully prepared to take as many pictures as possible during family gatherings or special events.

Olivia was predeceased by parents Wilson James Sr. and Lucille James Bowman and two brothers Wilson James and Freddie F. Wyche. Olivia's earthly memories remain to be cherished by her husband Linear C. Cherry Jr. of Chesapeake, Virginia, daughter Linette C. Hunter of Chesapeake, Virginia, son Kevin Harris and Michelle Harris of Virginia Beach, Virginia, son Linear C. Cherry III (Kathy), of Upper Marlboro, Maryland. She is also survived by seven grandchildren, six great-grandchildren, her dear and only aunt, 108-year-old Edith Hamlin of Hampton, Virginia, her nephew, Wilson James III, of Hampton, Virginia, her niece Darlene Butler (Michael), of Tampa, Florida, a special cousin Leonard Powell (Denese) of Hyattsville, Maryland, a special childhood friend of 78 years, Agnes B. Saunders Gatling of Newport News Virginia, and a host of nieces, nephews, relatives, and friends.

A Celebration of Life service will be held 1:00 pm Friday, December 11, 2020 at Pretlow and Sons Funeral Home, where viewing will be from 11am until 12:45 pm the day of the service. Interment will follow at Albert G. Horton, Jr. Memorial Veterans Cemetery, Suffolk.