Jason Caldwell’s Picks: This Week’s Top High School Football Games + His Mount Rushmore of Prep Legends
When it comes to high school football in Alabama, few eyes have been as sharp or as seasoned as Jason Caldwell’s. For nearly three decades, the veteran journalist has stood on the sidelines, notepads in hand, watching future stars carve out their early legends under Friday night lights.
@ClaudiasWorkshop 
Now in his 27th year covering Auburn athletics, Caldwell writes for the 247Sports Network and AuburnUndercover.com, but his roots in prep sports run deep. A proud native of Sylacauga, he has spent countless nights in bleachers and press boxes, documenting the rise of athletes who would later dominate college stadiums and even NFL arenas. In 2021, his dedication was recognized when the National Sports Media Association named him Alabama’s Sportswriter of the Year—a testament to his storytelling and the authority his voice carries in the world of Southern football.
The Magic of Friday Nights
For Caldwell, high school football isn’t just a stepping stone to bigger leagues, it's the heartbeat of small-town life. Each game is more than a scoreboard; it’s band music echoing across chilly autumn nights, cheerleaders shaking out pep in front of proud parents, and communities rallying behind boys who are still figuring out who they are.
Caldwell’s Mount Rushmore of Prep Football Players
Having witnessed generations of talent, Caldwell has compiled his personal “Mount Rushmore” of high school football greats. These are the names, he says, that defined eras, set bars sky-high, and left indelible marks on Alabama’s football history. Each player is chosen not only for raw stats but for the way they electrified a stadium, turned games into folklore, and set the standard for what Friday night greatness could look like.
This Week’s Top Games to Watch
Of course, Caldwell isn’t just about nostalgia; he's still laser-focused on the present. Each week, he breaks down must-watch matchups across Alabama’s prep football scene, spotlighting rivalries, rising stars, and the storylines that will keep fans glued to the action. Whether it’s powerhouse programs colliding or underdog teams fighting for respect, Caldwell has a knack for identifying the drama before it unfolds.
Why Caldwell Still Matters
What makes Jason Caldwell’s perspective so valuable after nearly three decades? It’s simple: he sees patterns others miss. He knows the difference between a good player and a generational one. He understands how a single game can alter the trajectory of a season—or a life. And above all, he still loves the game in its purest form, when the players are fueled less by NIL deals or professional contracts and more by hometown pride.
