The 6 Most Hilariously Inept Spies of All Time

6 Aldrich Ames

If Aldrich Ames ever got his own Bond flick, it would be called The Spy Who Loved Whiskey. He was frequently reprimanded for sleeping on the job at the CIA, a gig he almost didn't get because of his -- no shit -- repeated drunken brawls with police officers. That's right: Getting hammered and taking a few flying jump-kicks at a cop does not disqualify you from intelligence work. Ames was also chastised for having three extramarital affairs, which doesn't sound like any of the CIA's business ... until you realize that one of them was with a Colombian agent. But somehow, despite (or hell -- possibly because of) his sloppy cop fights and spy-banging, the CIA promoted him to the elite Soviet team in D.C. Hey, if this whole "subtlety" thing wasn't working out for the spy game, why not throw a crack squad of stumbling boozehounds at the USSR? You know: Fight firewater with firewater.

But astonishingly, the drunk guy with a track record of thinking with his dick didn't turn out to be a good choice to handle sensitive information. Ames contacted the Soviets in 1985 and turned traitor for money, which he handled with the usual stealthy grace we've come to expect from him. Instead of setting up a series of drops (standard practice for the spy community), Ames would just drive down to the Soviet Embassy, walk in with a box full of documents, have lunch with his contact, take his 50 grand and then walk right out the front door with the cash, presumably in a bag with a giant dollar sign on it.

And he kept this up for nine years.

The CIA finally caught on to Ames when somebody began to wonder why the guy snoring on his desk and using a bottle of Scotch for a pillow was driving to the office in a brand new Jaguar. Ames was being paid about $60,000 a year at the time, yet somehow managed to drop $540,000 for a house -- in cash! When they looked into his finances, the CIA found that even Ames' monthly phone bills exceeded $6,000. And when they finally did the math and figured out that donating plasma and recycling beer cans just doesn't pay that well, Ames suddenly left to attend a "conference" in Moscow in early 1994. But he didn't make it in time, and the agency moved on him. Now he's spending the rest of his life in prison, but only after making $4.6 million from selling CIA secrets.

Which is chump change, really. Barely enough to keep the phone on.

5 Edward Lee Howard

Edward Lee Howard began his career in the CIA in 1980, after working for the Peace Corps and USAID. He and his wife trained for two years and were all set to go to work at the American Embassy in Moscow and try their hand at spying until a polygraph test showed that Howard had been blatantly lying about prior drug use. Having learned something of a lesson from the whole Ames debacle, the CIA reluctantly let this promising addict go. Disgruntled, Howard hit the sauce, made some drunken phone calls to Washington and got arrested for fighting while intoxicated.

If you learn anything from this article, let it be that elite spies handle employment changes like teenagers handle a bad breakup.

In 1984, still angry at being fired, Howard met with a KGB agent in Austria and started supplying him with info. The CIA finally figured that the disgruntled former employee with the drug problem who was making slurred bipolar phone calls to them every night might have a hand in this and had the FBI monitor him. The Howards, by now living in Santa Fe, New Mexico, knew something was up from all the totally inconspicuous flower delivery vans and pizza trucks passing by, to the point that Howard himself went up to a member of the "covert" FBI monitoring team and told him that he was ready to talk. He just needed time to get a lawyer. Amazingly, the FBI let him go despite his flight risk, though presumably they did make him pinkie swear not to do any more treason. Amazingly, despite the sacred bond of the little finger, Howard skipped town the next day.

So how did Howard mastermind this escape? Simple: While he and his wife were returning from dinner, they made an impromptu dummy of Howard out of some rags and propped it up in the seat of their car. Then the real Howard leaped from the vehicle on a poorly lit back road and hightailed it to the airport. We swear to God we have seen that exact same plot deployed on Perfect Strangers, and we're pretty sure even Balki didn't get away with it. But Howard did: He flew to New York, then to Helsinki, where he finally slipped into the Soviet Embassy and defected. Howard eventually made it all the way to Russia, making him one of the elite few Western spies to manage the feat. He spent the last years of his life writing taunting books about his spy life, until he died in 2002 from a suspiciously broken neck.

Although given his track record, we kind of think it might have just been a pile of old laundry in the vague shape of an Edward Howard.

4 Russian MIT Spy Ring

In the early 2000s, the SVR (the KGB's successor agency) planted a ring of spies across the United States and United Kingdom who were so bad at their jobs that the FBI intentionally didn't catch them for a while, because they were just too easy to monitor. It was the world's first case of pity espionage. These Russian agents, who were all given anglicized names and placed in computer-based jobs at universities in London, New York and MIT, operated under a central ringleader named Anna Chapman.

Of their many, many stupid problems, the least of which was that the spies transferred data using highly unsecure PC-to-PC open wireless networking. This meant that information being sent to another computer could easily be intercepted and deciphered, as it later was. Slightly more significant a problem was that the spy programs kept freezing their laptops, so this elite team of Soviet agents -- who, remember, were posing as computer experts -- had to send them back to Moscow for troubleshooting. But perhaps the most ridiculously damning error was their logins. The team's laptops were protected by 27-character-long random passwords, which is good: They're harder to guess at, and harder to brute force, but sadly, also harder to remember. So the Russian spies just went ahead and slapped sticky notes with the passwords right there on the laptops. To paraphrase one of the most authoritative movies on spycraft in our generation, Spaceballs: "So the password is right there on the computer? That's the stupidest thing I've ever heard in my life! The kind of thing an idiot would have on his MacBook!"

When the FBI began to get suspicious of the oddly well-off IT guys who knew nothing about computers but everything about borscht, they checked out their records and discovered they had listed cleverly falsified information. And by clever, we mean they put down addresses like "99 Fake Street." When the bureau finally moved on the spy ring, they found a treasure trove of top secret stolen information ... right there on the spies' desktops, as icons.

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.

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."

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?"

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?

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.

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.