DANIEL HANDLER got into hot water last fall as host of the National Book Awards, when his "jokes" turned racist while giving Jacqueline Woodson an award for Brown Girl Dreaming. The author better known as Lemony Snicket apologized, and the We Need Diverse Books campaign accepted Handler's mea culpa in the form of a $110,000 donation.

Now on the heels of Handler's newest—the adult novel We Are Pirates—there might be another check in the mail. Filled with the champagne problems of a white middle-class family in San Francisco, We Are Pirates charts a dizzying spell in the life of radio producer Phil Needle, as he struggles to pay for his expensive condo and create a radio program about American outlaws. Even more so, it's about his discontent daughter Gwen and her spoiled, embarrassed existence. This teenage malaise takes the form of shoplifting, until she discovers the allure of a pirate's life thanks to a racist old man with Alzheimer's.

Handler's prickly story twists throughout the short novel, which makes for confusion that slowly gets resolved and circled back upon. Characters are namedropped, then abandoned until later. Connections feel more plot driven than fueled by motivation: Why is Gwen obsessed with pirates? Why does the mistreated black orderly turn to the outlaw life so quickly? Why is Phil casually racist? The characters are fuzzy at best, and flat at their worst. It's painful to see a great author (see Handler's Adverbs, Why We Broke Up, or the Series of Unfortunate Events) tread this murky water.

When Gwen's pirate life begins, We Are Pirates picks up steam. Fueled by a collection of books and a sassy new best friend, she plots to steal a ship from the harbor for a bloody outlaw adventure. But it feels like too little, too late for We Are Pirates. Handler, try as he might with his endless stores of cleverness and nautical wordplay, cannot buoy the story. He describes Phil as "a landlubber, with no sea legs even in his own house, and his daughter, his baby, was storming in the next room, unhinged, unanchored and grounded." The winks feel stifling, the switchbacks claustrophobic—and then there's the weird racial ickiness.

Take Phil's observation: "There was a look white people shared on the subway, when other people were misbehaving..." Or what's dished out to Manny, a Haitian orderly, whose name is not really Manny: "We talked about this," his retirement-home boss says. "The residents find it easier to remember than anything Jamaican." These lazily tossed grenades feel contextless, working only as cheap motivation to get characters to join the crew. Maybe it's too soon after Handler's disastrous emcee gig to get a clear perspective on We Are Pirates' subtext—as it stands, it leaves a bad taste. It's an uneven novel seeped in as much problematic history as its romanticized marauding namesakes.