Cashout, like most of the Fly Boy Gang-FBG members is part of the Gangster Disciples from the faction formerly known as ‘St Lawrence Boys’, and currently known as ‘Tooka Gang’. Cashout has been beefing with Chief Keef due to the fact that Chief Keef has dissed his gang ‘Tooka’ in many of his songs. The St Lawrence Boys was renamed to Tooka gang, in honor of one of their fallen members “Shondale ‘Tooka’ Gregory”. Cashout took the insults from Chief Keef personally since Tooka was a very close personal friend of his. As a result of Chief Keef’s disses, Cashout went out of his way to diss and humiliate Chief Keef any way possible.
Cashout list the song “3Hunna” by Chief Keef as one of the main reasons he’s beefing with Chief Keef. In the song Chief Keef says “F*ck a Tooka gang b*tch, I’m 3hunna”. Chief Keef has also dissed Tooka gang one of his songs titled “John Madden” in which he says “Where yo momz at ?, My d*ck she gone climb that – F*ck A Tooka Gang, I let this ruger bang”. Following this insult, Cashout called Chief Keef’s mom and put her on speaker admitting that she had sex with Cashout. The tape was recorded by Cashout without Chief Keef’s mother’s permission, and Chief Keef has yet to directly respond to the tape.
Cashout, whom was a close friend of Lil JoJo, a fellow Gangster Disciples member and rapper whom was killed in 2012, would shock many by beefing with Lil JoJo’s brother. Cashout released a song titled “Phone Call” which took some shots at Lil JoJo’s brother Swagg. Unlike Lil JoJo, Swagg was not a member of the Gangster Disciples. In the song Cashout attacked Swagg for not being real, among other things.