Complex sentence: Bomar most notably attended preparatory school at the Fitzgerald & Clarke Military Academy in Tullahoma, Tennessee, winning the state prep-school football championship playing with future Vanderbilt teammate Hek Wakefield and both the football and basketball championships under future Vanderbilt assistant Wallace Wade.
Split into simpler sentences: Bomar most notably attended preparatory school at the Fitzgerald & Clarke Military Academy in Tullahoma, Tennessee. He won the state prep-school football championship playing with future Vanderbilt teammate Hek Wakefield and both the football and basketball championships under future Vanderbilt assistant Wallace Wade.