There's More Than One Way To Wear A Wire

Guy Gentle Was An Undercover Wall Street Informant For The FBI. Then He Really Flipped

- Zeke Faux

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.

Gentile was feeling edgy about traveling stateside. It was July 2012, and regulators had been making calls about a stock play he’d been involved with a few years earlier. He’d been part of a group that the FBI suspected had suckered investors out of more than $15 million by manipulating the market for shares in a Mexican gold mine and a natural gas project in Kentucky.

As Gentile’s plane landed in White Plains, N.Y., he saw the flashing lights of police cars on the tarmac, confirming his fears. Before passengers could disembark, uniformed men came on board. Gentile dialed his lawyer, but the men grabbed the phone out of his hands, handcuffed him, and marched him off the plane.

Soon, two FBI agents picked him up from an airport detention room and drove him to a neon-lit diner in Newark, N.J., near their office. They bought Gentile a bacon cheeseburger and a Diet Coke and told him he had two options: Either they could throw him in jail, seize his assets, and hand his case to a prosecutor with a 95 percent win rate, or he could help them catch a bigger fish—and maybe make his problems go away. Gentile didn’t need to think it over. Whatever you want, he said, I’ll do it.