Novel: Tricky Business

Overview
Dave Barry’s Tricky Business is a comic caper set in South Florida that unfolds over a single, disastrous night aboard a shabby offshore gambling ship. With a tropical storm moving in and the ship’s decks crowded by retirees, tourists, hustlers, and crooks, a simple money handoff spirals into a violent, chaotic farce. Barry blends slapstick, hardboiled crime beats, and affectionate skewering of Miami’s talent for attracting schemes, turning a thin slice of time into a pressure cooker where greed, luck, and weather collide.

Setting and Premise
The action centers on a nightly casino cruise that sails just far enough from Miami to skirt gambling laws. It’s a floating microcosm of South Florida: neon-lit bars, tight-lipped security, indifferent management, and a clientele chasing jackpots or hiding from their lives onshore. What looks like another routine cruise becomes the chosen venue for a high-stakes cash exchange involving a drug-running operation. As the boat pushes into worsening seas, the storm strips away the thin veneer of order, leaving staff, passengers, and criminals boxed together with no easy escape.

Plot Summary
Barry threads multiple storylines toward collision. On the honest end are a struggling lounge musician hired for the night and a tough, quick-witted cocktail waitress exhausted by low tips and lousier men. Both are just trying to finish a shift when they stumble into the orbit of the handoff, seeing too much and attracting the attention of dangerous people. On the crooked end are a slippery courier hoping to skim the proceeds, a pair of inept heavyweights tasked with keeping the deal clean, and a colder, more competent enforcer who intends to leave no witnesses. Law enforcement watches from a distance, waiting for the right moment or for the criminals to implode.

Once the storm hits, the ship rolls, lights flicker, and the slots fall silent. Panic spreads. The cash changes hands and then changes hands again, chased through corridors, storage rooms, and the rain-slicked deck. Miscommunications multiply, guns come out, and the howling wind amplifies every mistake. The musician and the waitress improvise a series of escapes and small acts of courage, protecting each other and a few hapless bystanders while the bad guys undercut one another. By the time dawn approaches and the weather breaks, the scheme has unraveled. Some villains are dead, some are in cuffs, and the money has a fate more ironic than lucrative. The survivors limp back to shore a little poorer and a little wiser.

Characters and Dynamics
Barry populates the boat with sharply drawn types who bounce off one another at speed: an earnest working stiff whose decency makes him a reluctant hero; a weary but resourceful heroine whose humor keeps her steady; dim but dangerous enforcers who mistake menace for competence; a smooth operator who believes he can outthink chaos; and a gallery of gamblers whose faith in luck ranges from touching to delusional. The ship’s crew, equal parts cynical and overwhelmed, provides deadpan commentary as everything that can go wrong, does.

Themes and Tone
Chance versus choice drives the book: people come aboard to beat the odds, yet the storm reveals their habits and weaknesses more than their luck. Barry satirizes Florida’s boomtown scams and the fantasy of easy money, contrasting it with the quiet sturdiness of people who work, endure, and help one another. The storm acts as both plot engine and moral barometer, stripping away bluff and bravado. The tone stays buoyant even as the body count ticks up, with rapid-fire gags, sight-comedy set pieces, and lovingly absurd detail giving the crime story a bright, giddy spin.