The ancient Romans were actually pretty good at espionage; a consul in 300 BC actually used his Etruscan-speaking brother as a "plant" to convince the Etruscan people in Umbria's forests to convert to Rome's cause, and was successful. Unfortunately, the intelligence failures of the Roman intelligence services could sometimes be pretty aggravating and deadly. A Roman emperor instituted an intelligence service called the frumentarii, or "wheat-collectors," who operated across the empire and travelled widely, sending their information back to Rome. The problem, however, was that they basically became a free-for-all.

One writer compared them to a horde of locusts, and another noted that they basically ran an extortion racket. Apparently they'd ride into remote places and demand bribes from everybody to prevent a report going back to Rome about traitors and thieves. The Roman historian Aurelius Victor noted,

"These frumentarii, although they seem to have been instituted to search out and report on whatever disturbances were emerging in the provinces, by nefariously inventing false charges and instilling fear everywhere... they shamefully plundered everything."

Jay Robert Nash, in Spies: An Encyclopedia, called Hale "a great patriot but an inept spy." These days, he's mostly known for the phrase he uttered on being executed, "I only regret that I have but one life to lose for my country," but the circumstances of his actual life in intelligence are murky and don't seem to paint him in a particularly useful light.

Nash volunteered to spy on the British, then proceeded to wander around past enemy lines dressed as a schoolteacher (which he actually was), taking notes and sketches of vital military information. It's not entirely clear what got him captured; one of his relatives may have turned him in after seeing through his cunning disguise-that-wasn't, but one story insists that he was lured into conversation by a suspicious British Major who got him to admit his spying simply by pretending to be a spy himself. (Note: don't do that.)

It's also suggested that he just volunteered the information when he realized that his note-taking was getting him odd looks. It seems Hale was under the impression that being in civilian dress and without a weapon would somehow protect him from the usual consequences of being a spy. It didn't; he uttered his famous last words and was executed.

The gloriously named Captain Sir Mansfield Smith-Cumming would become the first head of England's Secret Service in the late 1800s, but his own life as a spy, as he freely admitted, was pretty inglorious and he was much better suited to coordinating other people than being out in the field himself.

The historian Harry Ferguson names three separate incidents in which Smith-Cumming created serious issues while trying to commit espionage. On one occasion he was caught in a consulate trying to get some letters that were being used for blackmail, and professed himself astonished because the people questioning him were disrespectful "even though he'd taken off his hat." On another he tried to have a conversation with a German spy despite speaking no German, spent most of it consulting a phrase-book in a panicky fashion, and only afterwards realized that they both spoke French.

My favorite, though, is the fact that he and a fellow spy once tried to book a quiet room with a source, but mistook a brothel for a hotel. "The madam," Ferguson writes, "faced with two men wanting a private room who said they were not interested in having a woman sent to them because they were waiting for another man, assumed they were dangerous homosexuals about to take part in a highly illegal act," threw them out and called the police.

He would go on to be a highly reputable intelligence head; he'd test the mettle of new recruits by stabbing himself in the (wooden) leg with a knife and seeing if they winced.

These days the starry-eyed people who've read too many Le Carre novels are likely weeded out of espionage jobs early on, but in 1908 the problem was in full force, and one ridiculous case brought it to the fore. Charles-Benjamin Ullmo, a French naval officer, decided to turn spy and stole a bunch of secret documents to fund his opium habit and the tastes of his very expensive mistress. Ullmo then proceeded to stumble through a catalogue of errors; he tried to sell the plans to the Germans, failed, then attempted to sell them back to the French again, who were understandably not very pleased.

Ullmo had all sorts of helpful suggestions to sort out the hand-off; he wanted to arrange money to be left in a train's toilet, and attempted to do the very Sherlock Holmes-ish technique of exchanging coded messages in the newspapers. When he finally showed up for a rendezvous, which was obviously a trap, he was dressed in an elaborate chauffeur's costume with a mask on, which is basically the most noticeable disguise ever. His lawyer basically said he was a flamboyant idiot caught in his own vaudeville play, and his life was spared, though he was put into prison on a remote island for years. There's no word on what the mistress thought of it all.

This one's just delightful, and it could also have been utterly horrendous had the plan behind it actually succeeded. In 1942, Operation Pastorius, run by the Nazis, deposited two groups of four spies in America, with jobs as diverse as bombing the hydroelectric plants at Niagara Falls and destroying the Ohio River bridges. Unfortunately for Germany, several of the people in the operation decided once they got to America (by submarine onto Long Island, of all places) that they didn't want to be German spies at all, and instead wanted to turn themselves over to the FBI.

The ringleader, a man named George John Dasch who'd once worked in America as a waiter, managed to accidentally get them sighted by the Coast Guard on the Long Island landing, tried to bribe a young Guard who immediately got suspicious, and eventually decided to turn himself in. To give himself courage, though, he went off to a waiter's club he'd known when he lived in New York and proceeded to gamble away vast sums of the money given to him by the German government. (The game, if you're interested, was pinochle.) Then he took the remainder of the money ($84,000), went to Washington, and physically dumped it all on the desk of an FBI agent, who must have had a very weird day. The operation was, needless to say, not a success.

The "honey trap," as it's called, is a basic part of many spy novels and plots: the beautiful woman who lures somebody into a compromising position, or gets him to give up secrets as pillow talk. East Germany's Stasi, however, opted for a gender-bending approach: to infiltrate the West German government, they created an entire league of "Romeo spies," clean-cut handsome men sent to seduce West German women in prominent positions and relay the information back home.

Many, according to the women who would later tell their stories, posed as members of international peace groups with noble aims, which enabled them to easily persuade their now-wives and girlfriends to give up vital information "for the global good." While the Romeos spread and created real issues for West German intelligence, Philip Knightley at Foreign Policy explained that they forgot one crucial detail:

"The scheme lost its usefulness when the West German counterintelligence authorities devised a simple way of identifying the Stasi officers as soon as they arrived in West Germany: They sported distinctly different haircuts — the practical "short back and sides" variety instead of the fashionable, elaborate West German style. Alerted by train guards, counterintelligence officers would follow the Romeo spies and arrest them at their first wrong move."

You're going to need to try a little harder to fool a woman.