The Ole Miss Rebels are in a bit of a bind today with WR Cayden Lee’s future. Even though his name is officially in the transfer portal as of January 16, he isn’t necessarily packing his bags just yet. It turns out this is more of a strategic “just in case” move rather than a definitive goodbye to Oxford. He actually wants to stay a Rebel, but there’s a big catch involving his teammate. Eligibility of Trinidad Chambliss.

“Additional info on Cayden Lee: The expectation is he’s going to withdraw from the portal and stay at Ole Miss if Trinidad Chambliss gets his waiver to be able to play next year, sources tell CBSSports,” Matt Zenitz on X. “Entered the portal to give himself options for if the waiver isn’t granted.” 

Cayden Lee’s future at Ole Miss is in the hands of Trinidad Chambliss. The engine behind Ole Miss’s record-breaking 13-win season in 2025. Cayden and Trinidad had a little bromance on the field. Cayden has basically made it clear that if Trinidad gets his waiver to play one more season in 2026, he is staying put.

Essentially, Cayden put his name in the portal to keep his options open just in case the NCAA plays hardball and doesn’t let his QB return. According to some, the only thing standing between Ole Miss making the playoff and 8 wins next season is Chambliss’ eligibility.

Right now, the legal side of things is a total mess. The NCAA officially denied Trinidad’s request for a sixth year of eligibility on January 9, because they claimed he didn’t provide enough medical paperwork from back in 2022 when he was at Ferris State. There is a lot of money on the line here, too, as Trinidad reportedly has an NIL deal worth up to $6 million waiting for him if he’s allowed to stay in college.

If the courts or the NCAA don’t give the green light, Cayden Lee is going to be one of the most wanted players on the market. Even though his stats dipped slightly in 2025. Finishing with 44 catches for 635 yards and 3 touchdowns. He is still considered an elite playmaker and WR1 in most of the Power 4.

LSU is particularly interesting because they are now led by former Ole Miss coach Lane Kiffin, who originally recruited Lee. For now, everyone in Oxford is just playing nothing but a waiting game. If the news is good this coming week and Trinidad is cleared, expect Cayden to pull his name out of the portal almost immediately to keep the duo together for one last run. But if the legal fight stalls? That would be something.

Expectations for the Ole Miss Rebels’ 2026 season with or without Chambliss

If Trinidad Chambliss wins his legal battle and stays for 2026, the vibe in Oxford is basically “National Championship or bust.” The Rebels were just one catch away from playing in the natty instead of Miami, and Chambliss finished top 10 in Heisman voting last year. Not going to lie, having him back makes Ole Miss an immediate top-5 favorite.

Plus, despite missing a couple of early games, the former D2 baller threw for almost 4ooo yards, 22 touchdowns and just 3 picks. That too, in the SEC. He has seven to eight 300 yards games. The consensus is that he could finish higher in the Heisman next season or even win if he comes back. If he doesn’t? Then Ole Miss might have to turn to the new guys they just brought in, like former 5-star recruit Deuce Knight or even Walker Howard, to try to fill some very big chip for the 2026 season.

As talented as they are, they simply don’t have the “been there, done that” experience of Chambliss. So there might be some growing pains early in the season. The Rebels would still be a very good, top-20 team because the roster is loaded with talent as it gets. But frankly, it becomes more about building for the future. Basically, with Chambliss, the ceiling is a trophy; without him, it’s about seeing if the young guns can step up and keep this Cinderella run going.

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