The 6 Most Hilariously Inept Spies of All Time

Spies get blown all the time (and in Bond's case, that's both literal and figurative). Some are uncovered through careful research by an enemy agency, some are betrayed by defectors and some simply die and are discovered after the fact. Others wake up in the morning, stick their foot in a bucket and pratfall their way through espionage until they accidentally trip and somersault into prison.

#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.

And, apparently, spray tan with spray tan.

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.

Yelling on the way out, "Thank you for the money you just gave me for all that spying!"

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.

Suckers. He would have taken 20 bucks and a case of Milwaukee's Best.

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.

It was like Burn Notice, but puffy.

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.

Via Wikipedia
"Wanted for breaking the digit-based honor system. Oh, and something about treason and betraying his country."

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.

It's hard to tell -- he actually kind of looked like some laundry.

#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.

At least she has the decency to look like a Bond girl.

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!"

"Oh, that? That's just a little joke. Hahaha."

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.

We're assuming with something like this as the icon.

Recommended For Your Pleasure

To turn on reply notifications, click here


The Cracked Podcast

Choosing to "Like" Cracked has no side effects, so what's the worst that could happen?

The Weekly Hit List

Sit back... Relax... We'll do all the work.
Get a weekly update on the best at Cracked. Subscribe now!