Confrontation with Tony
When Tony comes home in 1990 and sees a tower of Nike sneakers in Wes's room, he asks him where he got the money. Wes lies, saying that he's been DJing. Tony knows the truth; he beats Wes and walks out. He's furious that his brother chose to sell drugs and pursue a life of crime after all his warnings for Wes not to do so. It's the last time that Tony ever tries to talk to Wes about "the drug game" and the end of him hoping for a better life for his brother.
Soon after, his mother investigates and finds out he's been selling drugs.
Wes is taking a girl home when Ray starts yelling at her for being with a black man. Soon, he attacks Wes. He beats him. He gets inside and decides to escalate; he reaches for his Beretta and trades shots with Ray. Ray falls. The police come to pick Wes up soon after he gets home, cleans up, and hides the gun.
Because he's tried in juvenile court and because Ray survives, he only spends six months locked up.
Selling to an Undercover Cop
Wes isn't sure he should sell to the man who uses the wrong lingo. However, he's in a hurry and wants to make the sale, so he changes his mind after refusing him. When the man hands him the money, he sees that the nails are smooth and clean. This is a sign that the man is a cop.
He tries to get away but ends up being arrested again.