William Randolph Crittenden Jr.

June 13, 1983 – December 27, 2025

William Randolph Crittenden Jr., affectionately known by many as "Mr. Crittenden," "Little William," and "Wild Bill" passed away unexpectedly on December 27, 2025, in Winchester, VA.

Born on June 13, 1983, William was a proud lifelong resident of Winchester and a standout athlete at John Handley High School. A man of many talents and a vibrant spirit, he was a gifted artist who loved to draw and possessed a unique, creative vision. For the past three years, he was a dedicated employee at Knauf Insulation, where his friendly nature and warmth made him a favorite among his colleagues and everyone he met.

William's greatest passion was his community and the youth within it. He poured his heart into coaching basketball and football, serving as a mentor and a source of encouragement for many children. An avid Green Bay Packers fan, he brought that same energy and enthusiasm to every huddle and every family gathering. Above all, William was a man who consumed his family and friends with love and laughter, and he was a well-dressed man who loved his sneakers.

In the past year, William embarked on a journey of positive change in his life, showing a strength and resolve that made his entire family incredibly proud. His spirit and the impact he made on those around him will be remembered forever.

William is survived by his loving wife of five years, Mandy Crittenden; his children, Skye (Kamari Morgan), Malaya Sinclair, Emmary Crittenden, and Aubree Crittenden; and his stepsons, Trenton Ritter and Camden Moore. He is also survived by his parents, Helena, and William Crittenden Sr.; his sisters, Ebony Crittenden of Indianapolis, IN, and Sonya (James) Davis of Maysville, NC; his nieces, Hannah, Isabella, Sarah, and Sadie; and his nephews, James Jr. and Jeremiah. William proudly announced he would be a grandfather in July (Skye).

He was preceded in death by his stepdaughter, Sadie Ritter, and his beloved grandparents.

A celebration of life will be 11:00 am on Saturday, January 17, 2026, at Mt. Carmel Baptist Church with Presiding Elder Charles H. Boles, Jr.

Visitation will be at 10:00 am at the church.

Interment will follow at Shenandoah Memorial Park in Winchester, Virginia.

Ministry of Comfort Entrusted to
Cartwright Funeral Home
Winchester, Virginia
cartwrightfuneralhome.com