Pablo Escobar was loose. He darted across a noisy warehouse, searching for a corner to loom in.

He’s “kind of a bully,” said Duke Riley, the Brooklyn artist who trained him, watching Pablo flit around before landing on a ledge near the ceiling. Pablo Escobar is a homing pigeon, and an accessory — or an accomplice — to the latest exhibition by Mr. Riley, whose work often flouts both laws and common sense.

“Generally, I do things that don’t really seem that feasible,” Mr. Riley explained, “and then they tend to work out.”

But even by his standards, the pigeon project, “Trading With the Enemy,” strained credulity. In utmost secret, Mr. Riley trained a flock of homing pigeons to fly one way from Havana to Key West, Fla. Half the birds were flat-out smugglers, running Cuban cigars to the United States. The others were documentarians, outfitted with special cameras to record their 100-mile journey across the Straits of Florida.

The idea was to highlight the long history of pirating on the southern border, and also to thumb a nose, artistically, at the cutting-edge spy devices that may monitor the coast. Drones don’t care about pigeons.