Former MIT professor John J. Donovan Sr. was involved in a nasty legal battle with his adult children, with accusations of extortion and child molestation flying back and forth. One day Donovan got fed up and decided to end the dispute by implicating his son James of financial crimes ...
The Needlessly Elaborate Plan:
... so he shot himself. He didn't just fake a shooting; he really grabbed a rifle and shot himself twice in the stomach, then called the police and told them that his son had sent Russian hit men to kill him and his wife. Oh, and while he was at it, he also accused James of laundering $180 million.
"And don't even get me started on the Lindbergh baby!"
So, uh, why not go straight to the money-laundering accusations and skip the "shooting yourself in the stomach" part? How was the fake hit supposed to make the other part less disprovable? The police did search James' home that night, but when they didn't find any piles of cash lying around or any receipts written in Russian, he was cleared of any suspicion. And why did the hit men have to be Russian, anyway? We would have gone with Brazilian parkour killers, just to make the story a little less cliche.
Keep in mind, this wasn't something done in the middle of a drunken rage. The guy is an MIT-level genius who has written several books and given highly acclaimed lectures all over the world. He was cautious enough to rearrange security cameras so they didn't record him staging the break-in at his home, stepping into his minivan, and shooting his rifle four times. Granted, Donovan forgot another vital part of every criminal plan, which is "Don't have a to-do list with your plan in your pocket when the police come over," because that's exactly what he did.
Donovan was found guilty of filing a false police report, fined a few hundred dollars, and sentenced to some community service. On the other hand, his children filed a restraining order against him and won't be coming to any Christmas dinners anytime soon, so maybe that was his plan all along.
We've all had the misfortune of meeting a guy like Robert Hendy-Freegard, a used car salesman from the U.K. who lived off the money he leeched from the several women he'd somehow convinced to date him. But this particular douchebag wasn't content with merely mooching cash off of his girlfriends ...
The Needlessly Elaborate Plan:
... so he also pretended that he was a secret agent, convincing everyone he knew that they were part of an elaborate government plot.
So who cares, right? Right now there are thousands of dudes in bars bragging about equally ridiculous things. Well, the difference is that this guy had his friends carry out complex missions for him, just because.
Hendy-Freegard's modus operandi consisted of approaching women through his job and charming them into bed. Once he'd gained their trust, he would drop the bomb on them -- he was a secret agent working for MI5, a British intelligence service. But here's the catch: Just for hanging out with him these past few weeks, they were now in mortal danger of being assassinated by IRA terrorists. One of the victims (the only male) was at one point blindfolded and beaten, thinking that it was all part of the espionage adventure he'd been roped into.
"I just wanted to be seduced by a swarthy British spy!"
Hendy-Freegard would then tell his victims that, fortunately, he could make the danger go away if they just gave him a few thousand dollars to pay off the terrorists. These weren't just average ditzy people he was messing with, either: His victims included company executives, child psychologists and lawyers. The aforementioned male victim was sent on a bizarre quest that involved buying a copy of The Gay Times, reading it openly in the subway and then handing a can opener to a specific (nonexistent) person in a bar. The friend started suspecting that something might be wrong when he reported back to Hendy-Freegard and he just laughed his ass off.
Hendy-Freegard was caught when he told his American fiancee to ask her parents for $50,000 to pay for "spy school" -- they thought that was slightly weird and got him arrested. The thing is, a con man of his level could have made a nice enough living just squeezing women out of their money without the ridiculous secret agent story. Or, you know, sticking to selling used cars.
"No, no, the engine isn't leaking. It's deterring pursuit."
Alexandru Nemeth from Germany wanted a lot of money, and he decided that the corporate giant Nestle should be the one to give it to him. Nemeth successfully poisoned several Nestle products in over 20 cities across the country over a period of two years, but that was only phase one of his master plan ...
The Needlessly Elaborate Plan:
... with phase two being "pigeons." As in, sending carrier pigeons to deliver messages to Nestle demanding millions of dollars in diamonds, then using the same birds to bring the diamonds back to him. Because somehow, this was safer than just sending them an email.
Or just a good old-fashioned brick through the window.
First, Nemeth got hold of a bunch of pigeons, which his neighbors probably assumed he was just using for target practice. He then taught them to drop things off and come back to where he was staying -- training pigeons, in case you've never tried it yourself, isn't the easiest thing in world, and he had to do it all in secret while simultaneously traveling from city to city, leaving cyanide-laced drinks in playgrounds and things like that.
Nemeth then had his pigeon army deliver messages to Nestle leaving specific instructions for how he was to receive his reward for stopping the poisonous chaos -- in the form of small pouches full of diamonds, which would be attached to his birds. The pigeons would then take off and deliver the diamonds back to him. Knowing that, it wasn't hard for the authorities to figure out how to catch Nemeth using those same pigeons: They placed a homing beacon on the birds and just followed them in a helicopter about 200 miles to where the guy was hiding.
And yet not a single person in the entire Harry Potter series ever thought to do the same thing.
As far as criminal plots go, Nemeth was actually doing pretty well until he got to the "blackmail through pigeons" part. There was really no logical reason for him to communicate with Nestle through birds that are trained to lead back to him, other than a Batman-villain-level obsession with using feathered rats in all his crimes. We wouldn't be surprised if he was wearing a pigeon costume himself when they caught him.
For fictional villains who are guilty of this, check out The 6 Most Pointless Supervillain Schemes Ever Hatched and The 6 Most Pointlessly Elaborate Movie Murder Plots.