James Thomas Oyler Jr.

With broken hearts and profound sadness, our family announces the passing of our beloved son, brother, and uncle, James T. Oyler Jr., lovingly known as JR, who left us far too soon on June 6th, 2025, at the age of 64.

JR was so much more than a son and brother — he was a guiding light, a steady hand, and a heart full of compassion. His presence brought joy, comfort, and laughter to those around him. JR lived a life rooted in love and service, always ready with a warm smile, a kind word, or a helping hand. He had an extraordinary ability to make others feel seen, valued, and cared for.

He gave of himself freely — whether offering support during life’s hardest moments or simply being someone who would listen without judgment. JR’s kindness was quiet but powerful, touching countless lives in both large and small ways. He was the kind of person who showed up, who stayed, and who always made room in his heart for others.

He is deeply mourned and lovingly remembered by his parents, James T. Oyler Sr. and Barbara A. Oyler. siblings: Theresa A. Oyler Brown and her husband, Robert; Joseph H. Oyler III and his wife, Kimberley Schad Oyler; and John M. Oyler and his wife, Karen Brown Oyler, proceeded in death by his loving sister Kristine Marie Oyler Clinton. He also leaves behind his many nieces, nephews, great-nieces, and great-nephews — each of whom carries a special memory of his laughter, guidance, and boundless affection.

Professionally, JR was a dedicated and respected leader in the insurance industry. During his career at Hub International, he held several key roles, including Managing Director of Employee Benefits, Strategic Account Executive, and most recently, Small Business Manager. He took great pride in helping clients across Florida and beyond, managing VIP accounts with diligence, empathy, and integrity. More than his titles or achievements, it was JR’s humanity — his loyalty, humor, and fairness — that earned him the admiration of colleagues and lasting friendships throughout his career.

A memorial service to celebrate JR’s beautiful life will be held later in Virginia. We welcome all who knew and loved him to join us in remembering a life so generously and lovingly lived.

“Those we love never truly leave us. They live on in the kindness they showed, the comfort they shared, and the love they gave.”

1 John 4:21 “And this is the commandment we have from Him: whoever loves God must also love his brother.”