From Kingston to the Cage

Osbourne was born and raised in Kingston, Jamaica. In 2011 he immigrated to Wisconsin for a college wrestling opportunity under coach Benjamin Tones, who also coached fighters at an MMA gym on the side. After the wrestling season, Tones introduced Osbourne to head MMA coach Reese Shaner at Waukesha MMA, where he learned the fundamentals of martial arts.

He was a three-time state place-winner and first-year national qualifier in college wrestling before his program was shut down.

Osbourne signed with the UFC in 2019 after building a strong regional record. He is one of a small number of UFC athletes who maintains a full-time professional occupation alongside their fighting career — he works as an assistant teacher in Wisconsin, modeling possibility for his students every day.

'If my students physically see someone they know who came from the same background as them making big accomplishments, they will have no excuse to not do the same.'

Osbourne went through a difficult stretch in 2024 — losses to Jafel Filho and Ronaldo Rodriguez at UFC 306 at the Sphere — but bounced back with a second-round TKO of Luis Gurule at UFC on ESPN in April 2025. He is carrying a chip on his shoulder heading into 2026 and believes he won several recent fights that went the other way.

Osbourne is a physical flyweight with heavy wrestling athleticism. His striking is diverse — head kicks, knees, and hammer fists — and he has serious knockout power for 125 pounds. On the ground he is dangerous with the triangle choke he cites as his favorite grappling technique.

His heroes are his mother and God. He holds a two-stripe purple belt in jiu-jitsu. He is mission-driven — every UFC win is proof of concept for a classroom of kids in Wisconsin who need to see what's possible.