Rapper RondoNumbaNine, real name Clint Massey, was just 17 years old and fresh to the Chicago rap scene when he committed the crime of a lifetime in 2014. He was with a friend and fellow rapper Cdai, real name Courtney Ealy aged 19 when they approached a cab driver and fired multiple rounds into the driver's car.

Allegedly, the two rappers were part of a 3-car entourage riding through Chicago's South Side, looking for members of an opposing gang after an altercation earlier in the day. Javan Boyd, the 29-year-old driver, had been pulled over and was waiting for a passenger when a group of men, among these, RondoNumbaNine and Cdai, got out of their vehicle and approached Boyd's vehicle on foot. After asking Boyd if he was from the neighborhood, to which he replied yes, they fired a handgun seven times through the passenger door of his vehicle. Rondo's fingerprints were found on the vehicle, and a surveillance camera was able to capture footage of the shooting. This led to a 39-year sentence for Rondo and a 38-year sentence for Cdai.

Today, a new mugshot of Rondo has been released. It shows the now 20-year-old rapper in what looks to be a prison uniform with a white t-shirt underneath. His nondescript neck tattoo peaks beneath the collar.

Rondo, a Cook County resident, was a friend and frequent collaborator of rapper Lil Durk and was part of Durk's OTF rap group. Cdai was signed to Fredo Santana's Savage Squad Records.