NEW YORK » 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 Riley, whose work often flouts both laws and common sense.

"Generally, I do things that don’t really seem that feasible," 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, 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.

"I wanted to subvert this billions-of-dollars high-tech system with things that were being used in ancient Sumeria," said Riley, who researched pigeon history. In the early 20th century, they were regular messengers between coastal authorities in Cuba and Florida. "They would let a pigeon go," he said, to signify safe arrival.

With objects and video — and live birds — "Trading" is part of his solo show, "See You at the Finish Line," opening at the Magnan Metz Gallery on Nov. 1. He’s been promoting it by wheat-pasting posters around town.

In his artist statement, Riley, 41, calls himself a patriot, and he often sets his work on the waterfront, exploring the boundaries of institutions and authorities. In 2007, he was arrested after he floated a homemade replica of a Revolutionary War-era submarine too close to the Queen Mary II. ("Despite the fact that they were pointing machine guns at me in the pictures," he said of the New York harbor police, "they were actually very nice.") A 2009 performance in a reflecting pool in Queens, a staged naval battle, ended in a drunken, fiery melee.

This avian performance was riskier, Riley said, and he was coy about his methods. "How those cigars end up on the birds, I can’t say," he said, carefully. "If a bird ends up in my pigeon lofts, that happens to have a cigar from Cuba, and there also happens to be a pigeon that has a video camera on it, that shows footage of birds flying from Havana to Key West with cigars — yeah, I can’t really say how that happened."

The Treasury Department, which oversees the trade embargo with Cuba, was similarly flummoxed. "Oooookkkkkay," a spokeswoman responded, when told about the project by a reporter. In a statement, she added that importing or dealing in Cuban goods is generally prohibited for "persons subject to the jurisdiction of the United States."

Riley will say this: He started the training in Florida last year with 50 pigeons; 23 went on the first mission, this summer. Only 11 returned.

That’s par for the course with racing birds, he said, as he gave a tour of the colorful pigeon loft which once was command central in Key West. It had been shipped back to Brooklyn and stored in a friend’s metal shop. The cigar-carrying birds were named for notorious smugglers, like Pierre Lafitte, of New Orleans, and Minnie Burr, from Memphis, Tenn., who transported supplies under her skirts during the Civil War. The documentarians were named for directors who had trouble with the law, like Roman Polanski and Mel Gibson. Riley painted portraits — or, depending on your perspective, mug shots — of all 50, which detailed their efforts (Pierre completed his mission; Minnie, alas, was lost at sea) to display and sell at the gallery.

Also on view: the pigeons’ harnesses, worthy of Etsy, fashioned from bright bra straps with adorably embroidered smuggling pockets; the half-dozen Cohiba cigars they held, cast in resin; and a split-screen bird’s-eye documentation of the flight.

The pigeon-cam footage is shaky but mesmerizing. Riley and his small team labored for years to lighten the cameras, doctoring them to record at intervals from multiple angles. The birds shot hours of video: takeoffs, landings, ocean, and quite a few stops in between. "I didn’t know they were going to take breaks," Riley said.

A well-trained pigeon could make the flight in perhaps five hours. Some of his took two weeks. At least one landed on a Florida party boat, where it was quickly spotted, with cameras rolling. "It’s wearing a bomb!" a woman says, as a Jimmy Buffett song plays in the background.

Dara Metz, an owner of the gallery and Riley’s longtime dealer, said the piece, four years in the making, quickly appealed to her. It was, she said, conceptual, performative, political and funny — all hallmarks of a Riley work. Not that she knows how he does it. "When it comes to Duke’s projects, he’s always candid about what his intentions are," she said. "He does not get into the details about how he executes them."

She didn’t feel "Trading With the Enemy" needed the intervention of her lawyers, who might’ve cast a cold eye. "It might be bordering on illegal and pushing the envelope," but she said, "I don’t think he’s ever putting anybody in jeopardy, besides himself."

One pair of smuggler birds is for sale, for $100,000 apiece; the flock will be shown at Magnan Metz in the loft he built of wood salvaged from shipwrecks. Metz has enlisted interns and volunteers to care for the pigeons. "I’m hoping it’s as easy as he says," she said. (What she had yet to consider: Pigeons mate for life, breed in artificial light and heat, and gestate for 17 to 19 days. The gallery may soon be a hatchery.)

Riley, who makes a living as a tattoo artist and has birds inked on his body, was first entranced after he rescued a pigeon as a boy. "I let it go and it came back," he said. "You feel sort of connected to the animal after that."

He even lived with them in a cheap attic loft when he was a student at the Rhode Island School of Design. (The arrangement went over surprisingly well with girlfriends, he said: "You look like maybe a diamond in the rough — you know, like a sensitive bird-lover guy that just needs to be cleaned up a little bit.") He keeps pigeons in Brooklyn, and simply mailed some of their babies to Key West, which is apparently allowed.

But even with his decades of experience, this mission involved "a lot of trial and error," said Kitty Joe Sainte-Marie, Riley’s studio and project manager. The pigeons trained during hawk migration season and were prey. "One of them got nailed right in front of me," Riley said.

Others were felled by disease, faulty doors in the coops and temperament. "You have to build up their confidence, flying over water, very slowly," he said. Some of the strongest still disappeared on test runs. "It definitely doesn’t mean that they’re dead," he said. "They just may not come back."

Maybe the escapees merely feared the wrath of authorities. Riley admitted he was a little nervous himself. He envisioned pleading his case before a judge. "Am I at fault, or is the pigeon at fault?" he mused.

"A pigeon," Sainte-Marie offered, "would look real cute in handcuffs."