Dudley "Timmy 2" Simmons Waltrip Jr.

He was born to Dudley “Timmy” and Becky Waltrip in James City County and lived there his whole life. His love for construction began at a very young age while being his dad’s shadow. He worked for Dudley S. Waltrip and Sons Inc. alongside his dad and brother for almost 40 years. Timmy 2 became a master mechanic and started Waltrip Repair and Maintenance in 2022.

Timmy 2 was preceded in death by his father, Dudley S. Waltrip, “Timmy”.

He is survived by his mother, Becky Waltrip; son, Dalton Cruise Waltrip (Yasmeen); two granddaughters, Brantleigh and Raeleigh; sister, Lisa Waltrip (Robbie); brother, Brian Waltrip (Simone); sister, Dena Waltrip (Kip); along with many nieces, nephews, great-nieces, and great-nephews.

Timmy 2 will be missed by family and many friends until we’re all together again.

Visitation will be held at Nelsen Funeral Home, Williamsburg, VA on August 14, 2026, from 6:00 PM to 8:00 PM. Timmy 2’s Funeral Service will take place at James River Baptist Church, 4931 Centerville Rd, Williamsburg, VA on August 15, 2026, at 1:00 PM. A Committal Service will follow at Williamsburg Memorial Park Cemetery, 130 King William Dr, Williamsburg, VA.

Timmy 2’s favorite color was blue, and he loved wearing his blue jeans. Feel free to dress casually, wear blue, and jeans if you would like to.

In memory of “Timmy 2” Dudley S. Waltrip Jr, please plant a tree or give to the American Cancer Society (https://www.cancer.org/).