Greg McElroy believes Lane Kiffin is ‘struggling’ with whether he should leave Ole Miss

Greg McElroy believes Lane Kiffin is facing one of the most difficult professional decisions of his career. He’s thinking the Ole Miss head coach is genuinely torn about whether to leave Oxford for an SEC rival.

On Always College Football, McElroy said Kiffin’s admiration for the Rebels’ program and the support he’s been given over his tenure has made the decision far more complicated than outsiders assume. Behind the scenes, McElroy believes, Kiffin is wrestling with loyalty, his legacy and a rare championship window in Oxford.

“To be honest with you, I think Lane Kiffin is struggling with the idea of having to leave Ole Miss,” McElroy said. “He loves the program. He loves the resources they’ve given him to find success. This is a very difficult decision when it comes to what Lane’s thinking and where he’s ultimately going to end up.”

Alas, LSU and Florida are both pursuing Kiffin, with the Tigers viewed as the leader. But Ole Miss sits on the cusp of a CFP run, and that’s adding even more weight to his deliberations.

Moreover, a major question hovering over the saga is whether if Kiffin does accept another job, should he still coach Ole Miss through the Playoff? McElroy is adamant that he should.

“The best opportunity Ole Miss has to win a national championship is with Lane Kiffin on the sideline,” he said, pointing to Kiffin’s elite in-game value. He provides late adjustments, schemed-up leverage plays and subtle formation tweaks that can decide postseason matchups. Without him, McElroy believes, the Rebels might always wonder “what if.”

Continuing, he pushed back on the argument that Kiffin shouldn’t coach because he’d be recruiting against Ole Miss at his new job. McElroys’s point is everyone involved should prioritize the 2025 season, not hypothetical future rosters.

The former Alabama star framed it simply. If he were Keith Carter, he’d want the coach who built the run to finish it: “I’d want to give my team the best chance to hang a banner,” he said. “And the best chance to hang a banner is with Lane Kiffin on the sideline.”

Still, McElroy admitted the situation is fluid and unpredictable. If Kiffin leaves, Ole Miss could opt not to let him coach, and maybe the Rebels would still ride their momentum deep into the postseason. But if they fall short, the lingering question would be unavoidable.

With Ole Miss pushing toward its most promising season in program history and Kiffin weighing a career-defining crossroads, McElroy summed it up: “I really don’t know what’s going to happen. I really don’t.” Only the charismatic head coach does, it seems.