#3. Robert Hanssen
Robert Hanssen was an FBI agent from the 1970s until his abrupt termination in 2001 (heeeyyy, that's called foreshadowing!). By 1985, Hanssen, under the sexy yet inexplicable latin pseudonym of Ramon Garcia, began to work for the KGB. After a few years of casual treachery, the FBI deduced that a larger-than-normal amount of their agents were dying from a mysterious disease called "execution" and began to suspect they had a mole. A special task force headed by a single agent was assigned to ferret out this mole and uh ... groundhog(?) him with extreme prejudice. This lead agent was talented, this lead agent was driven, this lead agent was ... Robert Hanssen, of course.
Does anyone else hear that toothy "ding" bell sound when you see that picture?
Jesus, that's like bending to pick up a penny just as a wrecking ball flies over your back. That kind of wacky, unbelievable luck doesn't come along twice in a lifetime. But while any sane man would see the divine providence granted him and mend his foolish ways, Hanssen just figured that God was on the side of villainy these days and stepped up his incompetent spying game. He broke into the Russian Embassy, hacked into his fellow agents' computers and repeatedly refused promotions (that's right, he was doing such fine work not catching the spy that he was that the FBI tried to promote him for it) because he didn't want to take a lie detector test. Even his fellow agents tried to report him as a spy, but the FBI just laughed and shook their heads and said, "No no no -- he's the guy who catches spies. Easy mistake to make, Jenkins. Now, back to work you go."
But even the FBI can take a hint when you write it on a sack full of oranges and beat them about the head and shoulders with it, so they finally started investigating Hanssen. They found he had a password-hacking program on his computer, but he explained that he needed it to connect to a color printer. And the FBI believed him. They were all:
"What, that printer on the second floor, by Becky's desk? Haha, yeah, totally. That thing's always on the fritz. And this nuclear reactor? A stapler, you say? Sounds right to me! The 20th century; I tell ya, it's a crazy time. Welp, carry on."
"Printers, eh? They're goddamn ciphers."
But eventually, the FBI did gather enough evidence to arrest him. By stealing his phone. Where he kept his messages to the Russians. On his phone.
Jesus, we don't even feel safe keeping porn on our phones, much less high treason. But then, Hanssen was a different breed of man, whose hubris was only exceeded by his Mr. Bean-esque bumbling. But hey, at least he copped to it: When the FBI finally caught him handing over a garbage bag full of documents to the Russians (no briefcase for this worldly master of espionage), Hanssen simply said, "What took you so long?"
#2. Michael Bettaney
An important part of espionage is going unnoticed. Like the guy wearing a unitard on Casual Friday, the nail that sticks up is only going to be hammered down. After starting work for MI5, a British intelligence branch, in 1974, Michael Bettaney donned that proverbial unitard. And then he started singing old Nazi songs while he worked and loudly proclaimed his affinity for Adolf Hitler. Like many others in this article, Bettaney (who, it should be noted, was only hired in the first place in response to government pressure to hire more "working class" people) also had a drinking problem -- the drink being whiskey and the problem being that he would scream, "You can't arrest me! I'm a spy!" at the cops arresting him. Still, MI5 must have seen some kind of sparkle in Bettaney's glassy, unfocused eyes, because they promoted him up in 1982 to the highly sensitive Soviet desk.
Once there, Bettaney clapped his hands, cracked his back and immediately went to work ... taking pictures of classified documents and bringing them home to later sell to the Russians. MI5 somehow found out and began searching for a turncoat, but glossed right over Bettaney, because what spy in their right mind would be humming merry Nazi working tunes and saying, "Boy, I sure do love me some Hitler" right out in the open like that? By 1984, Bettaney had amassed armloads of documents and called the Soviets, ready to head East and trade the info for cash. He announced a "holiday" to Vienna, and his bosses, happy to be rid of him, granted the time off. But 24 hours before he was to leave London, the KGB themselves alerted MI5 of the spy in their midst. And they did so for the same reason the Brits couldn't believe Bettaney was their mole in the first place: He was just way, way too obvious. The Russians thought he was a piss-poor double agent that MI5 was trying to slip into their organization, and the tip-off was supposed to be their way of saying, "Come on, guys; how stupid do you think we are?"
"Seriously, you're fucking with us, right? Where's the camera?"
Bettaney then served 14 years of prison for his part, presumably while writing "THESE GUARDS WILL NEVER FIND THE PORN UNDER MY MATTRESS" all across the walls of his cell.
#1. Adolf Tolkachev
In 1976, Adolf Tolkachev, a worker at a radar station production facility in Moscow, was still upset with the communist government over how his wife's family was treated throughout the Stalin era. He decided to start passing information about the systems on to the Americans. So how did he plan to discreetly propose this espionage? Letters in invisible ink? Coded messages? Running after the American Embassy officials' cars, all the while screaming state secrets like a crazy person?
Huh. It was the last one. Who'd have thought?
Despite the fact that most American Embassy workers were already being tailed by the KGB in case they turned out to be spies, Tolkachev's approach was to sprint after cars with diplomatic plates and leave handwritten notes on the ones in the parking lot, which presumably read, "Do u want 2 spy wit me? Check dis box if 'yes.'" He did this for over a year, once even cornering the area's CIA chief at a gas station and pounding on his window. Much like Bettaney, the CIA thought this was a laughably obvious trap by the KGB. But after a year of chasing cars like a loose dog and leaving notes like a lovesick teenager, they thought they should at least hear the guy out. You know, make him feel like he was doing a good job at this spy thing; you don't want to hurt the little fella's feelings or nothing. But when Adolf started talking, the Americans discovered one of the best sources of information they had ever come across.
Be sure to read that link above to see some familiar names.
Adolf Tolkachev's legacy, before the Soviets finally arrested him in 1985, was to leave behind a huge technical advantage for America, and the disconcerting idea that the hobo banging on your windows at that stoplight just might be in possession of invaluable information.
For more on espionage, check out 5 Spies with Bigger Balls Than James Bond and 6 Real World Spy Gadgets Straight Out of the Movies.