Five-Star Alabama Commit Caleb Cunningham Returns to Ole Miss for Season Opener
OXFORD, Miss. — Ole Miss football kicks off its long-awaited 2024 season this Saturday in Vaught-Hemingway. It should come as no surprise that this begins another key opportunity for head coach Lane Kiffin and the Rebels to amp up their momentum on the recruiting trail. There will be plenty of playmakers in Oxford this weekend — including 5-star wide receiver Caleb Cunningham, an Alabama commit.
It is no secret that despite Cunningham’s commit to the Crimson Tide, the Rebels continue to let the Choctaw Co. Mississippi native know he is still a high priority and giving him food for thought as to why the No. 1 player in the ‘Sip should remain in the ‘Sip.
Cunningham was was last in Oxford during Juice Fest and returns this weekend for the season opener. It appears that while he remains committed to Alabama, Ole Miss remains on his mind. Despite the commit, it sure looks like this could be a photo finish between these two SEC programs for this elite talent.
Building the Foundation
His elite natural athletic ability on the football field and on the hardwood have separated him from the pack in the class of 2025.
As a freshman, Cunningham totaled 569 receiving yards and scored 10 touchdowns on 31 catches. As a sophomore, his impressive athletic skillset made him a standout on both sides of the ball where he caught 45 passes for 443 yards and 6 touchdowns.
In 2023, during his junior season, he set the record at Choctaw County with 48 catches for 1,138 yards and 14 TD.
Cunningham will look to create even more magic during his final season at Choctaw, and it starts this Friday under the lights as he heads on the road to face Parklane Academy. Kick-off from McComb is at 7 PM CST.
Degrees of Separation
Cunningham’s gifts on the football field not only stem from his devotion to the game, but also his hard work as a multi-sport athlete. He not only has made a name for himself on the football circuit, but he is quite the basketball player. Last season, Cunningham was named the Starkville Daily News All Area High School Basketball Player of the Year, helping lead his team to a district title.
He has scored well over 1,500 career points, averaging 18.4. points per game, 8.6 rebounds per game and 2.4 steals per game, to date, from his freshman to his junior season.
I be trying to tear them goals down 😂🔨 pic.twitter.com/YSOqxWQbU2
— Caleb Cunningham ✝️ (@calebcunning13) December 8, 2022
Cunningham’s athleticism is just elite, plain and simple, and it is no wonder teams — including Ole Miss — will continue to keep going hard to get him back home.
In case you needed a reminder, these are some of the things that you have to love about him when you watch him play.
Five-star @calebcunning13 doing what five stars do!
Big YAM Cunningham! pic.twitter.com/HTWRerzBBX
— Rion (Ree-un) Young (@MacCorleone74) August 24, 2024
Caleb Cunningham (@calebcunning13) , the uncommitted 5 ⭐️WR phenom from Choctaw County, combines blazing speed and unmatched versatility, achieving an IGA score of 89.5 matched with a max speed of 20.3 🔥#ReelSpeed #IGAScore
🔗 https://t.co/IKk5DVUWoB pic.twitter.com/M92BUFf3HZ
— Reel Analytics (@RAanalytics) June 4, 2024
Some of Cunningham’s traits that sit him atop the nation’s best are:
- The ability to separate with power and speed using his frame as a shield
- Physical ability off the charts
- Strong ability to break tackles and create yards after catch
- Speedy feet
- When it comes to the redzone territory, Caleb is the guy you want, especially with his ability to catch the ball at its highest point.
We look forward to sharing more about Cunningham and his visit this weekend. Hotty Toddy!
Lee Ann Herring-Olvedo
Herring-Olvedo sees college football the way championship programs do—from inside the personnel room. Every evaluation, every roster move, every recruiting battle tells a bigger story about identity, culture, and how a program is built to win in December, not just July.
With more than 15 years covering the SEC and the national recruiting landscape, Herring-Olvedo has built a reputation as one of the sport’s most respected personnel-driven voices—blending film evaluation, roster construction, and long-term program vision through a true front-office lens. Her coverage of powerhouse brands like Ole Miss Rebels and Kentucky Wildcatshas consistently gone beyond headlines, focusing instead on the blueprint behind winning programs: development, fit, culture, and recruiting strategy.
That foundation was formed early at Brown University, where she worked in player personnel and recruiting while competing as a student-athlete. Inside those recruiting operations rooms, she learned how elite organizations are truly built—through relentless evaluation, relationship building, projection, and trust in the board. Those experiences shaped the way she studies the game today: part scout, part storyteller, part architect.
Her analysis and reporting have appeared across major platforms including ESPN, NFL coverage spaces, USA Today Sports, and Saturday Down South. She also brought her personnel-minded approach to the airwaves as an on-air analyst for the Wake Up 502 College Football Show on Big X Sports Radio 96.1, where she became known for combining film-room detail with a wider understanding of roster identity and program trajectory.
In 2025, covering the rise of Houston Cougars football under Willie Fritz reignited the part of the sport that first drew her into football—the culture, the edge, the belief that a roster can reshape an entire city. That inspiration led to the launch of Coogs 365 Sports, a platform built to cover Houston athletics through a true scouting and recruiting lens while connecting the emotion of the game to the heartbeat of H-Town.
Now, Herring-Olvedo returns to The Rebel Walk where with an even deeper perspective shaped by years inside recruiting circles, national SEC coverage, and hands-on evaluation experience. Her return brings a familiar voice back to Ole Miss coverage—but with an evolved lens rooted in roster architecture, player development, and the modern realities of building championship-caliber football in the NIL and portal era.
For Herring-Olvedo, recruiting has never been about stars beside a name. It is about identifying competitors, projecting growth, and building a locker room capable of sustaining success. Her philosophy mirrors the best front offices in football: stack traits, trust culture, and never stop building.
