James Bond he was not.

With all the grace of a SoCal surfer being tackled during an episode of Cops, Ryan C. Fogle was arrested yesterday in Moscow for spying during an apparent sting operation by the FSB, the Russian foreign intelligence service.

Russian authorities announced that Fogle, a junior diplomat at the U.S. Embassy in Moscow, was an undercover CIA operative on his way to meet a Russian counterterrorism official he hoped to flip to the CIA. Within hours, he was declared "persona non grata" and ordered to leave the country. But to say that the circumstances surrounding the arrest were bizarre would be putting it mildly.

"There is a lot left to be learned about the whole episode," said Jeffrey Richelson, a Senior Fellow with the National Security Archive and an author of 13 books on the U.S. intelligence community. "And maybe we'll find some of that out. It's certainly not a shining moment in the history of U.S. intelligence."

The footage of his arrest, conveniently filmed by the FSB and released to Kremlin-financed satellite news channel Russia Today, showed Fogle—in a checked shirt and jeans—pinned under the knee of an FSB operative, an ill-fitting blond wig spilling out from under his baseball cap, looking more like a frat boy on his way back from a costume party than a wily graduate of The Farm.

The reality-TV ambience continued with a second FSB video, this time filmed inside the FSB's Lyubanka headquarters, showing Fogle sitting stone-faced, and perhaps even a little wry, as his captors lectured him and three other U.S. Embassy officials on the harm he'd done to U.S.-Russian relations.

The pomp and circumstance surrounding Fogle's capture were strange enough, but they seemed oddly fitting for a man whose tradecraft seemed to have been learned from a 12-year-old's how-to-be-a-spy kit. Found in his possession: a pocketknife, four pairs of sunglasses (always useful for a late-night rendezvous), a flashlight, 100,000 euros in cash, a cell phone circa 2001, a Moscow map, and a compass.

He also had a second brown wig, perhaps in case his contact preferred brunettes. A typed letter explained in almost childlike language how to set up a Gmail account and promised up to $1 million a year in return for the contact's cooperation.

"Maybe [next time] they'll get the wigs to stay on better," said Richelson.

Fogle's seeming amateurishness has more than a few experts wondering if the supposed sting was an FSB setup, a ploy on the CIA's part, or something else entirely. But while this particular case may appear out of the ordinary, when it comes to the intelligence racket, very few things are.

"As Yogi Berra used to say, 'It was deja vu all over again,'" said Peter Earnest, executive director of the International Spy Museum in Washington, D.C., and a former CIA operations officer. "Spy cases go on; they've been going on since recorded history and before."

And while it seems likely that the case of Ryan Fogle will be consigned to the dustbin of history, Earnest noted, the history of intelligence tradecraft is rife with plots both diabolical and dubious. For every polonium-laced teapot, there's often an exploding cigar to go with it. A very brief list of examples since World War II:

Operation Mongoose

During the heyday of CIA interventionism in the early 1960s, the CIA batted around ideas to assassinate Fidel Castro. For what was dubbed Operation Mongoose, at least eight plans were floated. In addition to the aforementioned exploding cigar, American operatives debated killing El Comandante via poison pills, contaminated air, poison-filled syringes, and even an I.E.S. (improvised exploding seashell).

Perhaps most bizarre, though, was the idea to lace his shoes with thallium salts in order to cause his beard to fall out. Ascribing Samson-like power to his facial thatch, the CIA hoped a beardless Castro would figuratively lose face with the people by literally revealing more of his own.

Assassination of Georgi Markov

The Bulgarian secret police, assisted by the KGB—the Russian security agency at the time—killed Georgi Markov, a Bulgarian writer and dissident, in 1978 in one of the most famous assassinations of the Cold War. While waiting to catch a bus on the Waterloo Bridge in London, Markov felt a sharp pain in his calf.

Turning around, he saw a man picking up his umbrella. Later that night Markov came down with fever; he died three days later of ricin poisoning. Scotland Yard suspected foul play. An autopsy revealed that embedded in his calf was a metal pellet the size of a pinhead, which had contained the ricin. The umbrella had been the delivery mechanism.

British "Spy Rock" Scandal

The British Secret Intelligence Service found itself in the hot seat in 2006 when the FSB announced, via an exposé on national TV, that it had intercepted a data transmitter disguised as a rock lying in a nondescript alley on the outskirts of Moscow. The football-size fake rock was packed with electronic and recording equipment and amounted to a modern-day version of a "dead letter drop" that allowed British officials to communicate with alleged local informants without ever meeting face to face.

The FSB had set up a secret camera weeks prior, filming men alleged to be British agents paying repeated visits to the rock, pacing by it, and on at least one occasion kicking it and carrying it away. (Was it glitchy? observers wondered.)

During the resulting diplomatic row, British officials indignantly rejected the claim as a work of fiction. But six years later, in 2012, the former U.K. Chief of Staff admitted to an "embarrassing" lapse of strategy. The Russians had Britain "bang to rights," he said.

Assassination of Alexander Litvinenko

The same year as the "spy rock" debacle, the writer Alexander Litvinenko, a former FSB officer living in London, fell ill on November 1 and died three weeks later. Litvinenko, who had been critical of the Putin regime, had been convicted of crimes in absentia in Russia following his flight to the U.K. in 2000.

In shades of Markov's assassination, the British investigation into his death determined the cause as radioactive poisoning by polonium-210 and pinned the blame on Andrey Lugovoy, a former KGB agent, who had met with Litvinenko that day at the Millennium Hotel bar. Though controversy still swirls around the case, most investigators currently believe that Lugovoy, likely under orders from Russian security services, slipped the polonium into the teapot from which Litvinenko was drinking.

2010 Russian Sleeper Spy Ring

In June 2010 the FBI arrested 11 alleged Russian intelligence officers living undercover in the U.S. under false identities. Never in the annals of U.S.-Russia relations had either country conducted such a massive counterintelligence roundup of foreign spies. But for all the smoke, there was very little fire. The Russians weren't even charged with espionage, since none had been able to obtain classified information during their many years of illegal residence.

For all the talk of shortwave radios, invisible ink, dead drops, and surreptitious exchanges of cash-filled shopping bags, the spies themselves seemed more interested in enjoying their American idyll than burrowing deep into U.S. corridors of power—none more so than the face of the spy ring, femme fatale Anna Chapman, whose red locks and curvaceous figure graced the cover of every tabloid in the land.