Ayo Shonaiya, a renowned music executive, entertainment lawyer, and filmmaker, has admitted that his biggest career regret was passing up the opportunity to work with the late Nigerian rapper, Dagrin.
Shonaiya recounted the emotional experience in a post on X (formerly Twitter) on Tuesday, reflecting on how his former personal assistant, Destiny, had introduced Dagrin to him at a hotel in Opebi, Lagos.
He revealed that Destiny was confident Dagrin would become the next big force in hip-hop, particularly because of his raw Yoruba punchlines.
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Seated by the swimming pool, Destiny played a couple of rough demos from a CD player.
However, Shonaiya confessed he wasn’t “really feeling it like that” and decided not to take on the opportunity to manage the budding rapper. They snapped a photo together before going their separate ways.
“Less than a year later, he had made Kondo, produced by a young producer named Sarz,” Shonaiya wrote. “I bumped into him again at Tee-A’s Lounge behind the Headies office off Allen Avenue in Ikeja. He made sure he reminded me that I passed on him. Lol.”
Shonaiya mentioned that they took another photo that night, and he genuinely felt happy for Dagrin’s success.
Tragically, that moment would be their last meeting, as Dagrin passed away in 2010 following a fatal car accident.
“Rest in peace Dagrin,” Shonaiya added. “Only God knows the heights you would have reached.”
Dagrin, whose real name was Oladapo Olaitan Olaonipekun, is remembered as one of the most influential rappers in Nigeria’s music history.
His hit tracks such as Pon Pon Pon and Kondo were instrumental in pushing Yoruba rap into mainstream recognition.
His passing at just 25 sent shockwaves through the music industry and remains one of the most profound losses in the history of Nigerian music.
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