Drake Joins Morgan Wallen Onstage in Houston Amid Gambling Losses and Lingering Controversy
Drake made an unexpected appearance in Houston this weekend, joining country music star Morgan Wallen onstage in a moment that has sparked both surprise and criticism. The Toronto rapper didn’t perform, but walked out with Wallen and baseball icon Roger Clemens, sharing the spotlight during one of Wallen’s tour stops in Texas.
Backstage, Wallen posted a clip of himself embracing Drake, soundtracked by the 6 God’s track “Under Ground Kings.” The video served as a public nod of respect toward Drake, who has long dabbled in genre-crossing friendships and co-signs.
However, the appearance didn’t sit well with everyone. Wallen’s presence in the music industry remains controversial after a 2021 video surfaced showing him using a racial slur. Though he issued a public apology and faced industry backlash—including being dropped by his label and removed from radio stations—the controversy ultimately boosted his profile, with album sales and streams surging in the months that followed.
Drake’s public alignment with Wallen adds another layer to a history of questionable endorsements. The rapper has appeared multiple times on Kick livestreams hosted by Adin Ross, a figure who’s also drawn criticism for allowing racial slurs and offensive content on his platform. For some fans, the connection between Drake and Wallen is raising familiar questions about where the superstar draws the line when it comes to who he supports.
Meanwhile, Drake is facing challenges of his own—particularly at the casino. In a recent Instagram Story, the rapper revealed he’s on a historically bad gambling run. A screenshot from his account shows that he’s wagered nearly $125 million over the past month and is currently down more than $8 million. Just last week, he lost almost $6 million alone.
“Gotta share the other side of gambling… Losses are so fried right now,” he wrote in the post. “I hope I can post a big win for you all soon cause I’m the only one that has never seen a max these guys max once a week.”
Following that, Drake placed another hefty bet—$800,000 on the Oklahoma City Thunder to win Game 6 of the NBA Finals against the Indiana Pacers. That wager also missed.
Still, the rapper remains hopeful. In a recent interview, Drake reflected on his biggest gambling win, which took place in early 2024 at a Dave & Buster’s, of all places. He recalled a wild night where a stranger called out roulette numbers and he hit on eight out of ten. “By the end of the night, we had won like $38 million, $40 million,” he said. “It was crazy. The craziest night ever gambling, for sure.”
With his stage cameos, social ties, and risky bets, Drake continues to keep his name buzzing—both in music and far beyond. Whether the Houston moment becomes just another headline or a deeper symbol of his willingness to embrace controversy remains to be seen.
