It is said that a true educator is always looking for a teachable moment – always seeking an opportunity to impart wisdom and knowledge by word and deed.  James Edward Bailey was a true educator – teaching us until the very end what it means to be a “family man.”  His greatest joy was being close to his beloved wife of 59 years, Etta Reed Bailey, their two sons Jarvis and Jarrett and daughters-in-law Monica and Tyra, and their six grandchildren Omari, Matthew, Skyler, Jaylon, Justin, and Jordan.

James Edward Bailey, son of James and Alma Bailey, was born on May 21, 1932, in Accomack County, Virginia.  He was the fourth of their eight children.  James, affectionately called “JB,” was a kind, soft-spoken, and gentle man. He was “Pop-Pop” and “Uncle JB” to not only his grandchildren, nieces, and nephews, but also to many other children who loved and adored him.  His students admired him and welcomed the advice and wisdom he shared with them.  He wrapped his iron resolve in a quiet voice, caring heart, and a velvet glove. JB worked tirelessly for many years in service to his community, with a primary focus of working with young people.  He was well known for giving rides and financial assistance to college students traveling to and from the Eastern Shore. His extensive contributions to local educational and faith-based organizations have touched the hearts of many people and improved their lives.

JB, a graduate of Virginia State University (VSU) and The University of Virginia, began his teaching career in Emporia, Virginia after a stint in the military.  Following those two experiences, he served in a number of positions – elementary teacher in Orange County; teacher and assistant principal in Accomack County; assistant director of student services at VSU; camp director for the Young Adult Conservation Corps, U.S. Department of the Interior Fish and Wildlife Service; hazardous waste coordinator at Quantico Marine Corps Base; and assistant principal at James Monroe High School in Fredericksburg, Virginia.

In all these careers, JB sought ways to maintain direct contact with young people and to find ways to help them make their lives meaningful.  His quiet manner of working with people and uncanny listening skills made him an effective “people person.”  When a colleague was asked to comment about JB’s “style” of working with people, he remarked, “When Mr. Bailey metes out punishment to students for infractions, they thank him, and leave his office with a smile saying Mr. Bailey is a nice man.”

JB was equally as effective when working with adults.  He was a Sunday school teacher and superintendent, Bible study leader, and a deacon at Holy Trinity Baptist Church and Shiloh Baptist Church (Old Site). He served as President of the Mayfield Civic Association and helped organize the Community Neighborhood Watch Program.  He established  and directed Fredericksburg’s Midnight Madness Program to provide summertime activities for youth in cooperation with Fredericksburg City Schools, Police Department, Parks and Recreation, and the YMCA.  JB served on several local boards, including the Board of Zoning Appeals for the City of Fredericksburg, Board of Directors for the Mayfield Civic Association, and the Rappahannock Community Services Board. He also served as a Commissioner for the Fredericksburg Parks and Recreation Department and a member of the Fredericksburg Host Lions Club, where he was the Chairman of the Bland Music Competition that recognized musical talent among middle and high school students.  JB was also a member of Kappa Alpha Psi Fraternity, Incorporated.

JB received numerous awards including the James E. Bailey Midnight Madness Program Award named in his honor by the Fredericksburg City Council, the Lions Club David C. Burks Award for service and dedication to Lionism, and the Juvenile Diabetes Research Foundation Award.  Additionally, JB generously supported the Bailey Family Endowment at Virginia State University.

Even in his retirement, JB continued to be a community activist, championing the creation of a farmer’s market in the Mayfield area. He also continued to demonstrate his faithfulness to his church, Shiloh (Old Site), with attendance at the 8:00 a.m. service, and he was always filled with delight when he was in the presence of his much-loved family.

JB’s survivors include his wife Etta, sons Jarvis (Monica) and Jarrett (Tyra); grandchildren Omari, Matthew, Skyler, Jaylon, Justin, and Jordan; his sisters Marguerite Young, Shirley Bailey, and Sylvia Johnson; brothers William Bailey (Gladys) and Eugene Bailey (Juanita) and special nephew Lonnie Bailey; children Linda Askew, Vincent Smith, and Marva Stanley and their children and grandchildren; and a host of nieces, nephews, cousins, and friends.  JB was preceded in death by his parents James and Alma Bailey, brother Weldon and sister Florence.

Funeral arrangements are being provided by the Keith Matthews Funeral Home of Norfolk. More information may be found at