Donald Trump and Lil Wayne

According to Skip Bayless, one of the most high-profile break ups caused by Donald Trump may have been Jalen Hurts and Lil Wayne.

Hurts recently signed a contract with the Philadelphia Eagles that made him the highest paid player in NFL history, only to be quickly surpassed by Lamar Jackson. The massive contract for Hurts was negotiated by his agent Nicole Lynn, who left Lil Wayne’s Young Money APAA Sports Agency for Klutch Sports in 2021. Hurts, who Lynn began representing in 2020, soon followed her to Klutch.

On a recent episode of The Skip Bayless Show, the Fox Sports host discussed Hurts’ decision to leave Lil Wayne’s sports agency and its apparent connection to Trump.

“I don’t know exactly why Jalen and Nicole left Wayne, I don’t,” Bayless said. “There has been some speculation that I’m vaguely aware of, that it had something, maybe a little something or a lot something, I don’t know, but something to do with the picture that was taken of Trump and Wayne when Wayne went to talk to Trump about that $500 billion package that was aimed at creating jobs for the Black community. That was back in October of 2020 and of course Trump, just before he left office, did pardon Wayne.”

After Wayne’s meeting with Trump, he shared a photo with the then-president of the United States on social media. Wayne later endorsed Trump for president, Trump then pardoned Wayne after he pled guilty to a federal weapons possession charge. Lynn officially joined Klutch about six months after the photo of Wayne and Trump was taken.

“I don’t know much about politics,” Bayless said. “I am not political, as my wife Ernestine will tell you. I did not vote for Donald Trump. All I know for sure is that Dwayne Michael Carter Jr. (Lil Wayne) has as big and good a heart as any human I have ever known. His heart was hurt over this.”

Bayless might not know much about politics, but he portrays himself as knowing a lot about Lil Wayne, regularly touting the friendship they have developed over the years. Considering their relationship, it’s reasonable to wonder if Bayless got this information about the Trump photo directly from Wayne.

Even though the photo is from 2020 and Lynn left for Klutch Sports two years ago, Bayless implied that he just recently learned of the possible rift over Trump. According to Bayless, he was a huge supporter of Hurts as recently as last year, which made it difficult when the Eagles played his beloved Dallas Cowboys. But following the breakup with Wayne, Bayless said, “That will no longer be the case,” implying he won’t have an issue rooting against Hurts after the quarterback left his friend’s agency.

[The Skip Bayless Show, photo from Lil Wayne’s Twitter account]

About Brandon Contes

Brandon Contes is a staff writer for Awful Announcing and The Comeback. He previously helped carve the sports vertical for Mediaite and spent more than three years with Barrett Sports Media. Send tips/comments/complaints to