Controversial comedian Charleston White is known for his blatantly explicit comments. Addressing the past of his upcoming opponent, the Island Boy, White serves up a couple of derogatory insults to describe how he prepared for the fight.
The comments stem from the event’s promoter, Adin Ross, asking the Island Boy how he prepared to fight a boxer with one eye. Charleston White has a glass eye. White would quickly refute the question by turning it around and revealing how he trained for his opponent.
“What is your technique, knowing he [Charleston White] has one eye?” Adin Ross asked the Island Boy.
Not allowing the Island Boy to speak, Charleston quickly responded with “He ain’t trained with a one-eyed guy. So how he know what to do with a one-eyed guy?”
Charleston White v. Island Boys
White would proceed to share how he trained for the Island Boy with the use of derogatory words. He added: “I been training with a si**y.”
The comedian’s insults stem from The Island Boys going viral in 2024 after the brothers kissed each other on a livestream. The Island Boys claimed they were paid to kiss each other.
Adin Ross would ask White how his training went ahead of the fight. Describing the process, White said, “It’s been great. The si**y was hittin’ the sh*t outta me like a p*nk. Like he was swinging. So I learned how to move.”
Charleston has fought in several celebrity boxing matches. The lead-up has always been controversial. White has struck an opponent at a previous weigh-in.
This match pits White against Redd—a member of the viral Island Boys duo known for music videos and antics. It marks a shift from provocative tweets and viral pranks to sanctioned sport. Their feud, once confined to online noise, now plays out in front of live audiences and thousands online.
The bout now headlines Brand Risk 008 as the co-main event. It airs live on Adin Ross’s Kick stream on Sunday, June 22 at 8 p.m. EDT (5 p.m. PT). For fans, it offers a rare blend of influencer drama and real-world stakes.
