- Years earlier, Spike and Vicious meet Julia at Ana's club. But romantic entanglements and Vicious' ambitions soon cause trouble for all of them.
- Prior to the current time-line, Spike and Vicious are underlings of the Syndicate Capo Stax, who assigns the duo to a job of negotiating a deal with the Neptune Cartel. It rains diamonds on Neptune and the Syndicate wants a piece of the distribution action. Stax wants the guys to open the negotiation at 40% and then settle at 25%. Vicious promises to get the full 40%.
Stax takes Spike to the side and tells him to keep an eye on Vicious, who is the son of an Elder. Stax says that he is grooming both Fearless and Vicious to be future Capos in the Syndicate. Stax says that Fearless is the one who always cleans up after Vicious and says that the Elders want Fearless on the Neptune deal just to make 100% sure that Vicious does not mess it up. Fearless and Vicious were meeting Stax at Ana's Jazz club. Fearless and Ana were good friends even back then.
Vicious plans to take over the Syndicate one day and wants Spike by his side. When the main act at Ana's is unable to perform, Julia takes center stage, instantly captivating Vicious and becoming the club's headliner. Vicious starts taking Julia out on dates.
Stax informs the duo that the Neptune cartel has a rule that all negotiations are carried out naked. Vicious botches the Neptune deal when one of the negotiators insults him and the Syndicate (Vicious cuts off his hand). Stax is furious with Vicious since this was their one chance of getting a foothold in the outer planets. This leads to Vicious straining his relationship with Julia and her getting closer to Spike. Spike is loyal to Vicious as he believes that Vicious saved him as a kid, when he convinced his father to take Spike in and build a life for him. Sike had grown up on the streets, with no parents, no prospects and no chances of survival.
Vicious is marked for impulsively murdering a Neptune thug. Vicious found the thug in an alley outside a night club and rammed him down with his car, while he was out cruising with Julia and Spike. Vicious asks Spike to take Julia home, while he tortures and kills the thug. This was the first time that Julia had seen the brutality of the Syndicate and was shaken. Spike comforts her and they end up having sex together.
Spike is ordered to execute him by Stax. If the Syndicate does not comply, it will be war with the Neptune cartel. Caliban, Vicious's father, sanctioned his death personally and he wants Spike to do it. Vicious learns that his father sanctioned his death. Feeling indebted to Vicious, Spike goes on to wipe out the Neptune Cartel instead.
He then tells Julia he is leaving the Syndicate life and wants to take Julia with him. Julia believes that Vicious will never stop hunting them, but Fearless convinces her that he will keep her safe. Julia agrees. They agree to meet under a bridge at night. Fearless goes to Julia to get new papers for himself and Julia.
Caliban informs Vicious that Fearless is planning to run away with Julia. Vicious tortures Ana for Fearless's location. He locks up Julia, so she cannot meet Fearless at the bridge as planned. Fearless's plans are foiled when Vicious' gang ambush and gun him down, sending him falling into a river presumed dead.
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