On the night he cut a deal with the FBI, Guy Gentile was on his way to a Connecticut casino for his cousin’s bachelor party. He’d jetted up from the Bahamas, where he was running an online stock brokerage that cleared a million dollars a year without much effort on his part. Then 36, he was a working-class kid who’d finagled his way into the dicier edges of finance, and he dressed the part, with neatly trimmed stubble, designer jeans, a silver Rolex, and sunglasses that hung from the collar of his tight T-shirt, just below a few tufts of chest hair.

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