A young Barry Keenan becomes obsessed with salvation after an angel appears to him in his mother’s basement. Convinced by the nuns at his Catholic elementary school that he’ll be doomed to an eternity of harsh penance if he doesn’t take drastic action, Barry starts looking for shortcuts to the promised land.
Bestowed by God with a divine prophecy for his salvation, Barry heads to a local bar to brainstorm his kidnapping. Deploying the business strategies he once relied on as a securities trader, he cobbles together what he considers to be an airtight plan: kidnap someone with rich parents, use the ransom money to invest in real estate, and pay everyone back with interest. Nothin’ to it. All he needs is a target, and some seed money to get things moving - both of which, he discovers, are hard to come by.
Having scraped together some cash and settled on Frank Sinatra, Jr. as his target, Barry assembles his rogues gallery of accomplices. In short order, he recruits his mom’s ex-boyfriend (and small-time mafioso) John Irwin, as well as an old friend he used to pull pranks with back in high school, Joe Amsler. But then, something unexpected happens: Barry falls in love with a woman named Pam. He’s certain she’ll dump him when she finds out about the kidnapping scheme, but much to his delight, Pam instead wants in on the caper. With his crew assembled, Barry heads for a state fair in Arizona to stake out Junior’s hotel…
Junior’s about to head to Europe for a run of concerts, and there’s no way Barry can afford to follow him there. After multiple failed attempts at the kidnapping - not to mention the seismic upheaval of President Kennedy’s assassination - Barry has a dark night of the soul. He resolves to give up on the Plan of Operation, and decides to give the scheme a send-off by drinking a bottle of whiskey. But somewhere towards the bottom of the bottle, Barry realizes he can’t bear to abandon his vision. When he discovers Junior’s making a pit-stop in Lake Tahoe before heading overseas, Barry decides to roll the dice one more time.
With Junior successfully nabbed at last, Barry and Joe make a death-defying escape from Lake Tahoe in the middle of a blizzard. Junior proves surprisingly compliant - even lending Barry a hand in his attempts to evade the police. Convinced that Junior’s cooperation is evidence of the divine inspiration fueling the Plan of Operation, Barry arrives back in Los Angeles after an all-night road trip feeling exhausted but hopeful...until Junior abruptly stops cooperating and starts playing hardball.
Barry and Pam sneak back into his hotel room in Lake Tahoe to clean up the evidence he mistakenly left behind the previous night. The place is crawling with cops and FBI agents, so Barry and Pam go undercover as honeymooning skiers, and take to the bunny slopes to evade capture. The plan works like a charm. But when Barry gets back to Los Angeles, he’s got a mutiny on his hands. Forced to improvise, Barry re-jiggers his ransom plan on the fly, and before long, he finds himself in a stand-off with the FBI.
While hiding out at a friend’s house, Barry counts out cash as the plot thickens around him. He’s lost track of his accomplices, and when he switches on the radio, he discovers he’s also lost Frank Sinatra Jr. By the time Barry tracks down John Irwin and Joe Amsler, there are sketches of his face on the front page of the LA Times. Time is running out - but as usual, Barry has a plan. And that plan is: to go Christmas shopping.
Barry makes one last attempt to ride off into the sunset with Pam, but by the time he makes it to her house, she’s got company. And it turns out the FBI’s been listening in on their phone calls. After a series of narrow escapes, Barry finally finds himself handcuffed and brought up on serious charges. And then, just as he’s writing out a confession, the man Barry hoped would be saved by the Plan of Operation (his dad) intervenes to save Barry from the Plan of Operation.
Barry’s trial is an overnight circus, and the evidence against him is overwhelming. But when Junior takes the stand and reveals his compliance with the demands of Barry and his accomplices, the defense team smells an opportunity. Determined to convince the jury that Junior’s kidnapping was engineered by the Sinatra family as a publicity stunt for his concert tour, Barry cooks up a story about a mysterious operative named Wes who put him up to the kidnapping. It’s a bold gambit - and, it turns out, a spectacular failure.
Back on the streets after four and a half years behind bars, Barry gets right back to scheming. Before long, he finds himself rich with casino money, and retires to a farm. But as the years go by, something starts to nag at him: even though the Wes gambit failed at trial, the narrative that Junior plotted his own kidnapping lingers in the popular imagination. Barry longs to tell his side of the story - but what if Frank Sinatra Senior won’t let him?