Benny Ray Caldwell

Benny Ray Caldwell passed away peacefully in Tyler, Texas, on November 7, 2025, at the age of 64. He was born on January 9, 1961, to Kenneth Wayne Caldwell and Bobbie Ann Caldwell.

Benny grew up in the Chapel Hill community, where his love for motorcycles, cars, and anything that ran on wheels first took root. He spent his life riding his Harley Davidson, working on cars, exploring backroads, and joining friends at motorcycle rallies that filled his years with laughter, stories, and the open-air freedom he treasured. If it had wheels, an engine, or a broken bolt, Benny could fix it. Day or night, you could find him in the garage, tools in hand, bringing machines back to life with his natural talent and steady patience.

Benny was full of charisma and deeply devoted to his family. He had a giving heart and never hesitated to help someone in need, whether he’d known them for years or was meeting them for the first time. He was loved by all who crossed his path and will be missed dearly.

On October 24, 2001, Benny married the love of his life, Charlene Caldwell, and together they built a home in Quitman, Texas, filled with loyalty, laughter, and shared adventures.

Benny was preceded in death by his father, Kenneth Wayne Caldwell; his brother, Joe Pat Caldwell; and his stepson, Merle Stephens.

Left to cherish his memory are his mother, Bobbie Ann Caldwell; his wife, Charlene Caldwell; his son, Brandon Caldwell and wife Shannon; his daughter, Kristen Reshae Caldwell and spouse JD; his stepson, Richard Runions and wife Madison; his sister, Deana Alexander and husband Dwayne; his brother, Kenny Caldwell and spouse Olivia; his stepmother, Kathy Caldwell; his stepsister, Kim Smith and husband Ray; his stepbrother, Greg Granberry and wife Kellie. He is also survived by seven grandchildren, four great-grandchildren, and many nieces, nephews, and friends who will hold his memory close.

Benny’s legacy lives on in the engines he rebuilt, the roads he traveled, and the countless lives he touched with his kindness and steady hand.

A Visitation with Viewing will be on Monday, November 10th, from 12:00 (Noon) to 2:00 P.M., at Faith Baptist Church (405 S. Hart St., Quitman, Texas 75783). Interment will follow at Smith Memorial Cemetery in Big Sandy, Texas.