Developer Michael Stern’s Maybach was idling in the driveway of his Miami Beach, Fla., estate when two people jumped the fence. But when they opened the door to try to make off with the car, his private security—an armed former New York City police officer—was sitting in the front seat.

“Cops are looking for them,” Stern wrote in a WhatsApp chat with his neighbors on tony North Bay Road soon after the incident on a February afternoon, attaching a picture of the two young men that appeared to be taken from a security camera.

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