Caleb grew up in the Daytona Beach area of Florida. He graduated from Warner Christian Academy in 2007, excelling both academically and athletically. Known for his dedication to fitness and passion for sports, he stood out among his peers.

In 2012, he graduated from the United States Naval Academy, where he was a two-year starting linebacker on the football team. He selected Naval Flight Officer as his service assignment and earned his Wings of Gold as an F/A-18F Weapon Systems Officer. He joined the Fighting Black Lions of Strike Fighter Squadron 213, based at Naval Air Station Oceana in Virginia Beach, Virginia. In 2017, he deployed aboard the USS George H.W. Bush (CVN-77) in support of Operation Inherent Resolve, conducting missions against ISIS in Iraq and Syria. On March 14, 2018, Caleb was one of two aviators aboard an F/A-18F Super Hornet that crashed while approaching Naval Air Station Key West during a routine training exercise.

His legacy lives on through his wife, Victoria (USNA ’13); his daughter, Rain; extended family, friends, and fellow service members.