Gerald Robert Williamson

October 15, 1947 – January 10, 2026

Gerald “Uncle Jerry” Williamson passed away on January 10, 2026. Born in Brockton, Massachusetts on October 15, 1947, Jerry lived a life defined by service, adventure, loyalty, and a personality that was anything but ordinary.

He spent most of his adult life in Redlands, California before moving to The Villages in Florida in 2022, where he continued to enjoy good company, great conversation, and his favorite pastimes.

A proud Vietnam veteran, Jerry served from 1968 to 1969 as a tank commander with the legendary Blackhorse Regiment. He held the rank of Specialist-5 (Spec 5) in Delta Company, 1st Squadron, 11th Armored Cavalry Regiment. His service was a defining chapter of his life, and his connection to the Blackhorse never faded.

In 2005, Jerry took part in what became known as the Senior Tour in Iraq, returning to active combat zones and participating in missions throughout the country. It is believed to be one of the only times in military history that veterans from the same unit were involved in combat operations in both Vietnam and Iraq with their original regiment. For Jerry, this was not about recognition. It was about loyalty, brotherhood, and standing once again with the men he proudly called family.

Jerry remained deeply involved with his Blackhorse family, attending reunions and staying closely connected with fellow veterans. The camaraderie, loyalty, and shared history meant everything to him. His daily emails, often filled with humor, personal updates, sharp observations, and thoughts on current events, were something many looked forward to each day. They reflected his wit, his patriotism, and his deep respect for those he served beside.

After his military service, Jerry pursued several careers, including working as a police officer, private investigator, and later as a therapist. Each chapter added another layer to a man often described as complex, insightful, and full of stories.

An avid reader and lifelong patriot, Jerry had a gift for conversation and storytelling. He especially loved bantering with wait staff and patrons at his favorite spots, where he could be found enjoying a nice glass of wine or a pour of Tullamore D.E.W., always paired with a good story and a sharp sense of humor.

Jerry lived an adventurous, meaningful life shaped by service, friendships, and unforgettable experiences. Those who were lucky enough to know him will remember his wit, his wisdom, his love of country, and his unwavering pride in his Blackhorse family.

In keeping with Jerry’s wishes, there will be no formal service or memorial. His nephew, Mike, will be making donations in Jerry’s honor to several of Jerry’s favorite organizations:

• The Blackhorse Regiment

• St. Jude Children’s Research Hospital

• The Tunnel to Towers Foundation

Those who wish to honor Jerry’s memory are welcome to donate to one of these organizations or to a charity that reflects something Jerry cared about.

A small celebration of life will be held in true Jerry fashion, with a glass of whiskey being raised in his honor.

Saturday, January 17, 2026

12:30 PM – 2:30 PM

Eileen Daly’s Driveway

2412 Morven Park Way

The Villages, Florida