Pink Lenny and a tattooed Brazilian talking in a bar. Lenny is telling the Brazilian a story about how he really scared someone one time ("You should've seen the look on the guy's face"). Then moment later, two gunman Charles Jericho and his gangster friend) burst through the door killing the Brazilian and everyone else in the room. Pink Lenny slipped outside the back door and gets away. The next you see Lenny, he's talking to someone on the phone before being confronted by a Brazilian telling him "Caine Knows he knows!" But the Brazilian ignores him and tells him to go with him. Lenny now in Havana, is being spied on by Tanner and Jones in his safe house before skipping town again later to be Vegas. There, he is confronted by Alvaro Vasquez, Solomon Caine's long time rival. Tanner and Jones meet Caine in Vegas, form a truce and work together on getting Lenny. Caine then gets Tanner to foil a lot of Lenny and Vasquez's plans such as Getting rid of a bomb planted at Caine's mansion and put at Vasquez business, blowing up shipment trucks belonging to them and holding the man who earlier confronted Lenny in Chicago, hostage to find out where Vasquez and Lenny are, he tells Caine that Lenny and Vasquez are gone to Rio and threatens him ("It's only a matter of time, Vasquez will come back for you") Caine however isn't effected by this and telling him "He can do what he likes dead man, I'm coming for Lenny" Lenny then revealed to have yet again skipped town and flew out to Rio De Jeniro with Vasquez, Tanner, Jones, Caine and Jericho meet together in Rio and set up plans to foil Vasquez. Jones however is suspicious of Caine and how Vasquez didn't stop Caine from entering Rio despite knowing he'd show up ("it's like he just let you walk in, you want to explain that to me?") Caine however ignores this ("Just find Lenny...I'll deal with Vasquez") and moves on. Jones then reveals to Tanner that Lenny then plans on skipping town again and that they are running out of time. Before knowing this, Vasquez sent out shooter out to kill Jones. Tanner however (warned by Caine) saves Jones but tells him to leave town. However Jones calls Tanner telling him that Lenny is leaving in a chopper and that Vasquez men are after him. Tanner goes to a water tower where Jones was hiding out only to find him unconscious on the ground but still alive with a gun shot wound. Tanner goes after the gunman and runs him off the road. Jones leaves Rio. Tanner reveals to Caine that Lenny is leaving and that he's going to go get him, Caine however orders Tanner to take Jericho with him, they both make it to Lenny on time to shoot down his chopper. Tanner then betrays Jericho revealing who he is, points his gun at him and tells him to put his Sawn-offs down and he does. Tanner leaves Jericho with a message to Caine ("Tell Caine I need Lenny more than he does") Jericho angrily threatens Tanner saying "I'll find you..." (Starting a big rivalry between those two). Tanner heads out after Lenny, chased him all over Rio while avoiding Vasquez or Caine's henchmen. The chopper finally crashes and Tanner finally confronts Lenny and tells him "You're in popular guy Lenny.. seems everyone wants you Caine,Vasquez, Rio PD, Me" but ends it by saying "Personally I don't care what you know". Lenny points his gun at Tanner but Tanner tells Lenny that he's "not going to shoot that" but Lenny ignored him and says "I am I am I'm gonna.." Before being disarmed and beaten up by Tanner. Back in Chicago, Tanner hands Lenny over to his boss, he questions Tanner about what will happen to Caine and Vasquez while Tanner responds by saying they will go "back where they were before" but his boss asks what he means and asks what else is about them apart from Lenny and Tanner closes it by saying "took a long time to figure out" and leaves the two. However it is revealed that the two were allied in the past and Caine has a Brazilian tattoo on his arm like Vasquez and his gang, the two ally together and shake hands at the Rio statue. After all this, Lenny's fate is unknown, he could of been put in jail or witness protection. Lenny is never seen mentioned or heard from again.