What's the Worst That Could Happen? 2001

As Kevin Caffery, a suave and clever thief, encounters Amber Belhaven while returning a stolen painting to her hotel room, he inadvertently stumbles into a tangled web of deception. In a bold reveal, Kevin discloses his criminal undertakings to Amber, surprising her at first, but soon winning her affection through his charm. As their romance deepens, Amber presents him with her father’s cherished lucky ring.

Meanwhile, Max Fairbanks, a flamboyant and carelessly extravagant businessman, is teetering on the brink of financial collapse, yet remains blissfully unaware of his dire predicament. His lawyer, Walter Greenbaum, urges him to act swiftly to safeguard his finances, but Max chooses to indulge in his lavish lifestyle, even hinting at a hasty bankruptcy filing. His wife, Lutetia, is unwittingly entangled in his deceit as he reassures her that his company is merely undergoing a minor “technical procedure” to mask the truth.

Through an acquaintance named Berger, Kevin learns of Max’s financial woes and seizes the moment to plot a heist. The two devise a scheme to rob Max’s opulent beach house, but their plan ultimately backfires when they are caught in the act. Max spots Amber’s stolen ring on Kevin’s finger and demands its return, sparking a high-stakes confrontation that allows Kevin to flee.

As tensions rise, Walter informs Max of a ban from his summer getaway due to his reckless flouting of bankruptcy regulations. Undeterred, Max clings to the superstition that the ring is a charm of good luck. Meanwhile, Kevin and Berger recruit the expertise of a skilled hacker, Shelly Nix, to trace Max’s movements via his email.

On a flight, Max consults with his cryptic psychic associate, Gloria, about the ring’s significance. Her unsettling drawing sends chills through him, but she keeps her worries to herself. With Max’s fortunes plummeting, he faces a judge who resists bribery attempts, resulting in an order for a public auction of his summer residence.

As Kevin and Berger ramp up their thieving endeavors against Max, the situation spirals into chaos. Sensing the escalating danger, Amber ultimately distances herself from Kevin, unwilling to be ensnared in the crossfire of their vendetta. When Lutetia unexpectedly discovers Amber adorned in stolen finery at a local venue, a confrontation arises, which unexpectedly forges a bond between them. They unite to devise a plan, driven by their shared struggle. Meanwhile, Gloria, increasingly unsettled by her tarot card reading, decides to cut ties with Max as his business partner. Her final decision comes when she hands crucial documents to Detective Tardio, setting in motion a series of events that will yield significant repercussions.

The scene is set for tumult at the bankruptcy auction, where Lutetia sends a skilled masseuse to distract Max while simultaneously pilfering the valuable ring. The criminals, led by Kevin, orchestrate chaos, utilizing smoke bombs and a fake video message as a diversion. Amidst the turmoil, Max finds himself confronted by Kevin on a sinking vessel, only to realize that the prized ring is nothing more than a worthless imitation. Just when despair seems imminent, Detective Tardio arrives, and Kevin pretends to be a hero by feigning a rescue of Max from the encroaching waters.

As they part ways, Amber emerges from the shadows as the clever masseuse who masterminded the heist. With a knowing glimmer in her eye, she advises Kevin to rid himself of the cursed ring, which has a notorious history of bringing misfortune. Accepting her wisdom, Kevin tosses the tainted trinket into the ocean and eventually reunites with his criminal associate.

In a final act of deception, Kevin adopts the persona of Max’s lawyer to manipulate the Senate hearing, ensuring a beneficial outcome for his client. Reveling in glory at a press conference, he makes off with one of Max’s exquisite watches, further cementing his reputation as an expert manipulator.