The most striking aspect of the history of espionage and informants is the sheer range of characters; exotic seductresses, Cold War moles, and gentleman criminals rub shoulders with today's wikileakers and hacktivists. The practice of trading information is as old as humanity, and individuals like those featured on this list will continue to shape the course of history, whether the general public knows it or not. Though many of the techniques have changed, the basic elements of undercover work have remained the same.
Each of the spies and informants on this list has been caught and punished in some way, whether it is by the death penalty or by virtual imprisonment in an embassy. Though these are the most famous examples of this particular breed, the most successful of their kind remain anonymous, carrying out their clandestine work behind the scenes of the modern political arena.
10 Julius and Ethel Rosenberg
In the summer of 1950 both of the Rosenbergs were arrested. First Julius in July, then Ethel in August. Within a year the American couple had been executed on the charge of conspiracy to commit espionage. They were accused of heading a spy-ring which gave the Russians information relating to the atomic bomb. Their trial was the subject of wide debate, and is generally seen as the peak of Cold War hysteria and anti-Communism.
The death sentence was defended with strong words by President Dwight D. Eisenhower when he said that "By immeasurably increasing the chances of atomic war, the Rosenbergs may have condemned to death tens of millions of innocent people all over the world. The execution of two human beings is a grave matter. But even graver is the thought of the millions of dead whose deaths may be directly attributable to what these spies have done."
9 Eddie Chapman
Eddie Chapman's life reads like a film script (and has actually been the subject of a sub-par film, and several books): It's the story of a one-time professional safe-cracker, who was imprisoned for robbing a nightclub, only to become a spy for the Germans. When Chapman first appeared on the Nazi radar after the the German occupation of the Channel Islands, he was deemed worth recruiting. German intelligence made the assumption that the fact that he was still wanted by the British Police would make him a worthwhile agent.
As soon as Chapman parachuted into the UK he turned himself over to the the British intelligence, who were expecting him (the German codes had been cracked, and almost all of their spies captured). Maintaining German confidence he turned spy for Britain, and Chapman spent the rest of the war acting as Agent 'Zigzag' - a name that recognized the double agent's erratic backstory which included having two fiancées in two separate war zones (between the UK and Norway).
8 Hector Xavier Monsegur (AKA Sabu)
In an interview under his alias Sabu, Hector Monsegur said: “I’m not some cape-wearing hero, nor am I some supervillain trying to bring down the good guys. I’m just doing what I know how to do". Sabu's skill set involved the hacking and disruption of millions of computers, a string of large corporations, and several governments.
Sabu was involved in the splinter group LulzSec, which was linked to notorious hacker group Anonymous. In 2010 and 2011, within certain hacker circles, his name was associated with attacks on PayPal, Visa, MasterCard, and the governments of Tunisia, Yemen, Algeria, Zimbabwe, and even the US Senate.
Unbeknownst to his fellow hacktivists, in the summer of 2011, Sabu was arrested by the FBI, and spent 10 months working as an informant. The information he gathered in that time resulted in the arrest of five suspects, and meant that a 'considerable' amount of time was deducted from Monsegur's 122 year potential sentence.
7 Anna Chapman
In 2010 Anna Chapman was one of the ten deep cover Russian operatives arrested in a sting operation by the FBI. The ten spies were returned to Russia in a trade, and each of the individuals disappeared into cushy Kremlin jobs. Except for Chapman, the flame haired femme fatale that the Western media couldn't get enough of.
In a decade-long operation the ten Russian spies had failed to return any information of value to the Russian government, but despite this apparent lack of success Chapman now enjoys a lifestyle normally reserved for celebrities in her home country. She has registered her last name as a trademark, has released a fashion line, featured in a number of steamy photo-shoots, and even has her own TV show.
6 W. Mark Felt, a.k.a "Deep Throat"
In the thirty years following the Watergate scandal, the identity of the most notorious anonymous source in history remained a mystery. It was not until 2005 that the truth would finally emerge, in a Vanity Fair article in which William Mark Felt revealed himself to be the asset codenamed 'Deep Throat'.
In 1972 the informant Deep Throat passed information concerning the Nixon administration to investigative reporters at the Washington Post. Various cloak and dagger techniques were employed to keep the FBI agent and the newspaper men in contact. These included reporters placing flowerpots in windows to signal a need to talk, and Felt marking a reporter's copy of a paper to indicate meeting times.
5 Bradley (Chelsea) Manning
Last August former soldier Bradley Manning was sentenced to 35 years in jail - over two decades less than the amount sought by the US military. Anyone even faintly in tune with current events will know about Manning, but many don't understand the extent of the damage this low-ranking intelligence analyst managed to do cause within the American military.
The 700,000 classified files which Manning passed to Wikileaks constitutes the largest breach of secret data in the history of the US - the most notorious of these files was the gunsight video of an Apache helicopter attack on a 'suspicious' group of Iraqis that included two Reuters journalists.
4 Ian Fleming
There are a number of parallels between Fleming and his philandering literary creation, James Bond; the two men share a taste in clothes, women, and gadgets. Unlike Bond, Fleming was never in active service during the war, but was instead involved with the Naval Intelligence office, where he held the rank of Commander - the same rank he would give to his character.
In the early 40s Fleming was also involved in the coordination of British and American intelligence work, including the establishment of the CIA. Fleming was associated with a number of operations in his time with Naval Intelligence, but the most Bond-like of these was unfortunately never carried out: Fleming suggested that a captured German plane would be filled with British commandos and crashed into the sea. After sending out a distress signal, the commandos would capture the German rescue ship and steal the vessel's naval codebooks. A great idea, perhaps (and an early indication of this author's fantastic imagination) but one that didn't come to fruition.
3 Mata Hari
Potentially the most notorious female spy in history, Margaretha Geertruida Zelle MacLeod was an exotic dancer, courtesan, and German spy who was executed by firing squad on 15 October 1917. Following a failed arranged marriage to a Dutch colonial captain, Hari moved to pre-war Paris, where she gained notoriety for her sensuality and eroticism. Her most famous act saw her slowly shedding layers of clothing leaving her standing in nothing more than a jewelled bra.
As a citizen of a neutral country in the first world war, Hari was able to move across borders with greater ease than most Europeans and this eventually led to her using her mobility to acquire information for the German intelligence. On February 13th, 1917 Hari was arrested in her room in the Hotel Elysée Palace, and accused of passing information which had led to the deaths of 50,000 soldiers.
2 Julian Assange
Australian Assange has a history of high-profile hacking operations dating back to the 1980s, but with his Wikileaks site he blew the lid on almost earth-shattering expanse of governmental and industrial corruption. WikiLeaks and its founder Assange have dropped out of the media focus over the last few months. The Cumberbatch film has come and gone, the television crews have largely left the Ecuadorian embassy in London, and the spotlight has moved to other areas.
Meanwhile, Assange continues to live in a small converted office space in the embassy, where he has political asylum. He lives with an internet connection, laptop, bed, treadmill, sun lamp, and kitchenette. The charges he faces in Sweden (where he is also accused of rape) will expire in 2020, but for the foreseeable future Assange will wake up in a building with bullet-proof windows.
1 Edward Snowden
Snowden worked for the NSA, and used his privileged position to turn on the organisation and reveal the extent of the agency's spying activities to the world at large. In a recent article Guardian Journalist Glenn Greenwald wrote about his first meeting with Snowden in Hong Kong. Although Snowden hadn't vacated his home for long, he told Greenwald that he had already been notified by an internet enabled security device that two NSA agents had just arrived at his house.
At that moment, he knew that the world's most powerful intelligence agency had identified him as the source for one of the biggest security information leaks in American history. The fact that the chase was now on must have been claustrophobic at best. The events of the following weeks - which would see Snowden taking up residence in a Russian airport with the eventual offer of a visa by Putin - have been written about to death, but the long-term impact of Snowden's espionage remain to be seen, as mainland Europe, the UK, and US begin to engage in the debate on privacy which Snowden's actions sparked.