By OBBM Network Editorial Staff

Derived from an episode of Locked In With Ian Bick.

He was bruised, bloodied, and still grinning when a towering girl named Love knocked him to the ground in a South Jamaica playground. That moment earned him the nickname “Smiley,” a label that would follow him from the streets of Queens to a maximum‑security cell in New York State.

Roots in South Jamaica

The guest, a native of South Jamaica, Queens, grew up in a crowded household where his mother cared for fourteen foster children alongside her own. He recalls his sister Janet, a foster child, and the chaotic environment that left him feeling like a foster kid himself. Overweight and self‑conscious, he was often teased for smelling like “tuna fish,” a detail that underscored the harshness of his youth.

His first taste of violence came not from a gang but from a confrontation with Love, the six‑foot girl who “whooped his ass” after he tried to defend his sister. The irony of smiling through the pain gave birth to the nickname that would become his identity.

From Small‑Time Dealing to a Conspiracy Charge

Seeking money, he turned to selling low‑level drugs, a path that eventually intersected with the world of G‑Unit and other street figures. A violent incident at a Burger King—where he knocked out a disrespectful customer and his friends—led to police attention. Shortly after, he was implicated in a conspiracy to kill a New York City police officer, a charge that resulted in a 20‑year sentence, of which he served 16½ years.

During his time on the streets, he also spent moments at a Dominican cabaret where a trainer named Joselito introduced him to boxing. The sport became a crucial outlet, offering discipline and a way to earn respect that he had never known before.

Surviving Prison: Boxing, Reputation, and the “Angel of Whoop‑Ass”

Inside prison, his boxing skills set him apart. He describes how one‑on‑one fights gave him a sense of power and a reputation that kept him safe: “When I fought, I’d say, ‘You remember me? You remember what you did to me?’” He admits the feeling of vengeance was intoxicating, yet he also recognized its danger, noting, “I was a hurt person hurting people.”

He earned a GED while incarcerated, a milestone he says helped him detach from the “seasonal” relationships of street life. He reflects that the only constant love he felt was from his mother, stating, “The only person that genuinely loves me in this world is my mother.”

Life After Release: Reflections and a New Direction

After his release, he returned briefly to the streets, reconnecting with former associates and the G‑Unit scene. However, the years behind bars left an indelible mark. He now spends his days “fighting his demons,” acknowledging that survival required harsh choices but also expressing a desire to break the cycle of poverty.

When asked if he is proud of his past, he answered, “No. But I think that God was sending me to rectify certain things. I’m a firm believer that God set me as the angel of whoop‑ass.” This paradoxical view highlights the complex blend of faith, regret, and a lingering sense of purpose that guides his post‑prison life.

Ian Bick’s conversation with the former inmate offers a raw look at how a childhood nickname, a love of boxing, and an unbreakable will can shape a person’s journey through the darkest corridors of the criminal justice system.

The full episode of Locked In With Ian Bick is available on OBBM Network TV.