What's The Worst That Could Happen? - Plot

Plot

Kevin Caffrey, a thief and connoisseur is at a local auction looking for things worth stealing. He meets Amber Belhaven who is auctioning off her father's painting to pay a hotel bill. When Kevin asks Amber about her hotel room which leads to Amber asking if he was trying to sleep with her, Kevin blinks rapidly and lies while also telling her that when he blinks he lies. When Kevin asks Amber if he could see her sometime Amber pretends to have the same thing Kevin has and says yes. While knowing what hotel she was staying in, he shows up to her room with the painting she auctioned off, having stolen it. Kevin tells Amber about his stealing business which shocks Amber at first but she accepts it in order to be with Kevin, and she later gives Kevin her father's lucky ring.

Elsewhere, Max Fairbanks, a snarky businessman who's company, TUI, is going into bankruptcy, is going over with his lawyer Walter Greenbaum on how to save his company. He tells his wife Lutetia Fairbanks that his company is in a technical procedure to disguise what his company is really going into. Kevin goes to a local bar in which his Uncle Jack owns to see Amber. Whilst inside he also runs into his friend Berger, who is also a thief and happens to know what places to hit. While having Kevin going outside to tell him about Max Fairbanks, he shows him an article about Max's current situation with his company, as well as what he couldn't access due to the critical condition of the chapter 11 bankruptcy code which includes going into his Beachfront mansion.

Kevin & Berger goes to the house to rob it, but Max captures Kevin. Before the cops take Kevin away, Max spots Amber's ring and tells the cops that the ring was also stolen. Kevin is forced to hand over the ring. After escaping from the cops, Kevin returns to the beach house to get his ring back from Max but fails to find him. Kevin, angry at Max finishes off what he started by robbing Max of the valuables inside the house and one of Max's three cars outside. Kevin tells Amber that the ring was stolen from him.

Kevin and Berger hire Shelly Nix, a computer hacker, to track Max's whereabouts by e-mails. During an airplane flight, Max talks to his associate Gloria, a psychic, about the ring. Gloria consults her cards, and draws a king with 5 daggers on his head. Shocked at the result, Gloria doesn't tell Max what she drew and pretends that she breaking up. Max meets a judge that he thought he paid off to keep his house, but his insults lead to the judge ordering him to sell his house & his contents at a public auction.

Upon knowing Max's plan to go to a cocktail party and then head to his beachhouse for one final visit, Kevin and Berger with the help of his partners Windham and Edwina rob Max's house. The next morning Max found out that his house have been robbed and meets with Detective Alex Tardio of the Robbery Division. Having enough of Kevin stealing from him, he calls his Head of Security, Earl Redburn.

Kevin finds out from Shelly that Max is going to Washington for a Senate hearing and has an apartment there. Kevin and Berger go to Washington to Max's apartment. There, Kevin learns that Max intends to secretly bribe the senators, and replaces the bribe money with insulting notes in Max's name. Max and Earl later storm into the apartment, having deduced Kevin's presence there. In the ensuing scuffle, Kevin tries to steal back the ring, but instead steals Max's wedding ring. Amber decides that Kevin's feud with Max has gone too far and no longer cares about the ring. While Max later addresses the Senate Committee he gets a call from Kevin who tells him that if Max will give him his ring back he will give him back his. Max refuses and proceeds to repeatedly curse at Kevin. To the senators, and other viewers, it appears he is speaking to them, with the result being that the hearing ends very badly for Max. While going back to his apartment back in Philadelphia, Walter quits being his Lawyer and Earl tells him that he was hacked, Max tells Earl his plan to get Kevin once and for all.

Kevin goes to Jack to find out where Amber is, Jack tells Kevin to stop robbing Max out of personal conflict and to forget about the ring. But when Berger tells Kevin about Max's bankruptcy auction and for how much his auction full of valuables is worth, Jack wants in on it too. Max gets a call from Lutetia about Max's behavior on TV, and tells him not to come home, while Amber breaks up with Kevin due to his obsession with Max and the ring. Lutetia finds Amber at Jack's bar wearing a jacket of hers that Kevin stole from their house and confronts her, Amber tells her that Max stole the ring she gave to Kevin. Knowing that they now have the same situation, they come up with a plan.

Gloria, who is thinking about Max still draws the same card and decides to come clean. Noticing how bad it is, she tells him to put an end to it but Max still refuses to give up Kevin's ring. Realizing Max's arrogant determination to keep the ring, she quits being his associate, and goes to Tardio to give him Max's Company's records.

At the bankruptcy auction, Lutetia tells Max that she wishes him well and sends him a masseuse. While Earl keeps looking out for Kevin through his monitors, Berger, Jack, Windham, and Edwina start the plan. Edwina and Windham are disguised as waiters, Berger is disguised as the auctioneer while Jack is his associate, and Shelly hacks into Max's security system. The crooks steal as much as they can, and later flee. Windham plants smoke bombs to cloud their escape and calls the fire brigade. At 2:00 Shelly plants a video of Kevin delivering a message to Max that he was being robbed without him being there on Earl's monitors.

Max, angry and enraged goes out into the smoke to find Kevin, but a firefighter, actually Kevin in disguise, drags him out of the smoke, stealing the ring in the process. Kevin steals Max's boat to escape, but Max jumps onto the boat and struggles with Kevin to get back the ring. While hitting a buoy causing the boat to sink, Kevin and Max find out that the ring is a fake, the ring having an inscription inside it that said: "Grow up." a message that they both got from their lovers. Max realises that Lutetia had got the masseuse to steal the ring during his massage.

When Tardio finds Max and Kevin, Kevin tells Tardio that he was saving Max, while Max tells Tardio that he never met Kevin. Kevin thanks Max and tells him that he owes him one. While going back to the hotel where Amber used to be before she moved in with Kevin, she shows him the ring revealing that she was the masseuse. She tells Kevin that the ring had bad luck and that he should throw it away. Kevin agrees and flings the ring out of sight and gets back together with Amber. Max and Kevin, who is pretending to be his lawyer, fixes the Senate hearing and went into the press conference victorious. When it is over Max and Kevin part ways, but as they do so, Kevin steals Max's watch.