In the wake of the recent Bernard family scandal and subsequent cratering of its financial fortunes, Andy comes to the unhappy realization that it's going to be necessary to sell the family yacht. Despite his sudden competence in dealing with the crisis, he takes this pretty hard, as he always wanted to sail it but never got the chance. So to cheer him up, Erin takes him to where it's docked in the last hours before it's sailed off to its new owner in the Bahamas. The plan is for one last sunset sail, but the dock employee won't allow that. So Andy up and decides that he'll sail it to the Caribbean himself.
Oscar takes the documentarians aside and confesses his affair with Angela's husband, unaware until too late that Kevin overheard everything. So now he's in the position of counting on Kevin to keep it secret, a task Kevin finds quite difficult in the face of various comments from Angela. Oscar maneuvers to have Kevin suspended, but thinks better of it and calls it off. And when the Senator shows up at the office and Oscar nearly freaks out, he's certain Kevin's about to spill all the beans. Fortunately, Kevin has a well-timed bout of temporary forgetfulness instead.
Dwight volunteers to be interviewed on a local radio show, but when the guest spot is cancelled, nobody tells him. Instead, Jim, Pam, Darryl, and Nellie conspire to cast him unknowingly in a Dunder-Mifflin version of War of the Worlds, spinning an alternate narrative in real time that begins with accusations of toxic paper and culminates in Dwight talking David Wallace down from what he thinks is an actual hostage crisis. This without Dwight ever getting wise to what's going on, even though he's in his underwear. Again.
Andy does indeed sail away from the dock in the family boat, but his crew is going to be his little brother, playing hooky from rehab and in need of a long cruise to dry out. So Erin's left high and dry. Well, except for how Pete is more than happy to help her fill some time in her suddenly empty social calendar.
Crossing the parking lot, Oscar asks, "Can you guys come with me for a minute?" Who? Oh, he's talking to the documentarians, who follow him behind the building where he confesses his affair with Angela's husband, the senator. "I hope that I can count on your sensitivity, maturity, and discretion," he says into a rolling camera. And then, out from behind a stack of pallets steps Kevin, who has none of those things.
Andy's holed up in his office with a bunch of unfamiliar-looking financial advisers as Jim and Pam bring us up to date: Andy's father blew all of the Bernard family's money and ran away to Argentina with another woman, and his brother Walt, Jr. locked himself in the wine cellar. But they're most horrified with how Andy has been so..."competent." Oh, and speaking of squandered fortunes, Jim and Pam don't seem to be fighting about that $10K he sank into his business venture on Halloween any more. Andy admits in a TH from his office that the "Nards [are] hurting," but he's doing so well at dealing with it that he wishes his dad could see him now. "'Course, he caused this whole mess so fuck him."
In the stairwell, Oscar tells Kevin that he's in love with Robert and he needs Kevin's help keeping it a secret until he can sort it out. "I really want to," Kevin assures him. "Whatever happens, always remember that." Or maybe "assures" isn't the right word.
Pam gets off the phone and reports that a local radio host named Iris Black wants someone from Dunder Mifflin to guest on her show today. This must be the most boring radio show ever. Dwight quickly volunteers, because he thinks it'll make him famous and that being famous will help him sell more paper. Like it does Brad Pitt.
Meredith asks Andy for leads on his brother in rehab, but is disappointed to learn he's in New Mexico. "So how you holding up?" she asks, rallying quickly. "We're done here, Meredith," Andy says with startling competence. Kind of a shame that Josh Groban won't be back, though.
Dwight sits at his desk doing tongue-twisters and vocal warm-ups, preparing for his radio interview but really just irritating everyone.
Andy has Erin, Andy, and Darryl in the conference room going over some unstealable Bernard family assets, including a boat whose sale would cover his mom's expenses. Alas, Andy's not willing to part with it, so he asks for other ideas. Oscar is distracted by Kevin talking to Angela at the copier, and snaps his name from the open door until Kevin remembers himself. Back in the conference room, Daryl's just finished calculating that selling everything but the boat will set Andy's mom up for six months, but Andy still isn't entirely cool with letting go of the floating family heirloom, even though he reluctantly agrees to do so. "What are you going to do, cry about it?" he THs, just before running off-camera to go cry about it.