The 5 Worst Deals In the History of Handshakes


It is the way of the modern world that when one man prospers another is getting a nice length of shaft instead. Perfectly fair deals are few and far between, and while it's tempting to think that short-pour on your martini is the single biggest rip-off ever, you would be tragically mistaken. History is full of true stories of people who got the absolute shortest end of the stick... presumably somewhere in the "butt" region.

The Manhattan Deal (Is Not What You Think It Is)

The 5 Worst Deals In the History of Handshakes

We all heard the story while growing up: Back in the day, the Dutch settlers bought Manhattan island for $24 worth of trinkets from gullible injuns who had no concept of property rights. But that's not quite the whole story. See, the Native Americans knew damn well what property rights were, and had known for centuries before the Dutch showed up. Also, the Dutch bought the island from the wrong people. And finally, the purchase price was actually 60 guilders which works out to an even $1,000 in today's money.

The 5 Worst Deals In the History of Handshakes

Wait, what was that middle thing again?

Yes, it turns out that the Dutch expedition led by Peter Minuit actually purchased Manhattan from the Canarsie Indians, who were based out of Long Island. They only used the island of Manhattan as a convenient place to get shitfaced, and were by no means the rightful owners (that would be the Manhattoes). So when a bunch of surly Dutch traders showed up and offered to buy the place, the drunken Canarsies readily accepted. Basically it was an old-school version of the "Wanna buy the Brooklyn Bridge?" scam--except this one actually worked.


So the whole situation is less like a crafty white guy buying a gold mine for a pittance from some poor, suffering widow, than it is a quasi-retarded white guy wandering by a bar and offering to buy it--cash in advance of course--from the first drunk he sees passed out in the gutter out front. On the down side, this was still a shitty deal for the Manhattoes, who presumably came by the next day and wondered who the dickheads moving into their houses were. But on the upside, it was a pretty fantastic night for the Canarsies, who got history-altering wasted and somehow came out of the whole thing a grand richer.

Well, until white people murdered them too. Then it was pretty much all square.

Portugal Gives Away the World


You wouldn't know it now to look at them, but at one point Spain and Portugal were the biggest superpowers in the world. So when the New World was discovered, you best believe that they were all over that shit like filth on a hobo. Unfortunately, property law of the day was pretty much limited to shouting, "But I was here first!" and then taking all plaintiffs to the High Court of Abdomen Stabbing.

So the land-grab turned into a big ol' funny hat-wearing slap-fight until eventually, both governments were fed up and sat down to negotiate terms peacefully. The solution they came up with, which they called the Treaty of Tordesillas, was based on logic straight out of a Three's Company episode: They simply pulled out a map of the New World, drew a line down the center, and let the Spanish have everything to the West while the Portuguese got all the stuff to the East.

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Which seems fair enough... until you look at that same line on a modern-day map:

Treaty of Tordesillas line


See, the problem with 15th century maps is that they just slapped down as much as they knew, colored the rest in with dragons and called it a day. So Portugal wound up with a tiny chunk of uninhabitable rainforest, while Spain ended up with pretty much all of South and Central America. Eventually Portugal figured out the terrible trick that Fate had played on it and desperately tried to expand its borders, but the Spanish had already settled in around them and blocked all their efforts. After a while, the Spanish felt sorry for the Portuguese and allowed them to expand to the current-day borders of Brazil, which netted them even more uninhabitable rainforest.

The 5 Worst Deals In the History of Handshakes

Just look at this uninhabitable hellhole!

To add insult to injury, just as the Portuguese had finished developing Brazil into something worthwhile, the ungrateful natives rebelled against them and took back the country (this may have had something to do with centuries of oppression, but mostly it was just plain old bad manners). With its only colony of any importance gone, Portugal's power faded into obscurity. Spain, on the other hand, enjoyed superpower status for several hundred years, proving that all any country needs to be great is a shitty cartographer and a stroke of luck.

MikeRoweSoft Takes On Microsoft, Wins

The 5 Worst Deals In the History of Handshakes

Back in August of 2003, a 17-year-old Canadian by the name of Mike Rowe decided to set up a website for his part-time web-design business. The name he chose was, and the more observant of our readers will have noted that this bears a striking similarity to a certain software mega-corporation. So it's not exactly surprising that the humorless executives from Microsoft found out about Mike's site and immediately asked him to take it down due to trademark infringement.

When Rowe asked for some sort of compensation, they offered him the kingly sum of $10. No, we're not missing a few zeroes there: One of the wealthiest companies in the entire world decided they couldn't afford to spend more money on Rowe than they would on a plate of Fajita Bely-Blasters at Applebee's. Oddly enough, Rowe declined this generous offer and was served with a 25-page cease-and-desist order instead of delicious, flavored-fired quesadillettes.

The 5 Worst Deals In the History of Handshakes

But as the gears in the mighty Microsoft war machine began rumbling towards court, Mike Rowe did an unexpected thing: He talked to the press. As the media started having a field day with the news, somewhere deep in the Microsoft hive mind, someone finally realized that they were taking a freaking teenager to court over a sophomoric pun and that this just might possibly not be the best PR for a company already one Death Star short of villain-status in the public eye. With the amount of backpedaling that followed, Lance Armstrong could have ridden the entire Tour de France in reverse.

To start off, they paid all of Rowe's legal fees as well as the cost of shifting his website to a better service provider (on account of the massive traffic boost he was experiencing) leaving him with a tasty $6,000 extra. They also sent him a brand-new Xbox and a full library of games, gave him and his parents an all-expense paid trip to a tech festival at Microsoft's Washington HQ and paid for a Microsoft certification course and a subscription to Microsoft's Developer Forum. In short, they set up his entire career for him and gave him some sweet things to do in his off time.


Oh, and that 25-page cease-and-desist thing? Mike Rowe auctioned it off on eBay for $1,000. And though it's pure speculation on our part, this just might be the thing that made Bill Gates rage-quit the tech industry for good.

A Little Old Lady Cheats Death (and a Lawyer)

The 5 Worst Deals In the History of Handshakes

One day back in 1975, a dapper middle-aged French lawyer by the name of Andre-Francois Raffray had a devil of an idea: He sought out a 90-year-old woman named Jeanne Calment, who was currently living in a very nice apartment indeed, and offered a deal: He would pay her 2,500 francs ($500) a month for the rest of her life if, when she died, he could take over the apartment regardless of how much money had been paid in total. The benefits were obvious: Once the old lady kicked the bucket a few months later, the Frenchman would move in after paying only a fraction of the actual cost of the apartment, presumably while twirling his mustache and cackling diabolically at the foolishness of the sweet old crone.

The 5 Worst Deals In the History of Handshakes

Fortunately for Raffray, she agreed. Unfortunately for Raffray, things most decidedly did not go according to plan. There were a few warning signs of what went wrong: Jeanne's mother had lived to 86, her father to 93 and her brother to 96, while Jeanne herself was unusually active, taking up goddamn fencing lessons at the age of 85. When most people stop controlling their bowels, she was just starting to learn swordplay. Even so, nobody was prepared for what happened next: Namely, that Mrs. Calment would live to be the oldest person in the history of the world.

The 5 Worst Deals In the History of Handshakes

The months turned into years into decades, with no sign of the old biddy dropping dead anytime soon. All this would only have made the moment Raffray finally moved into the apartment all the sweeter... if the old biddy in question hadn't outlived him. Yes, that's right: After 30 years of waiting impatiently, Raffray died before he could collect. What's worse is that his wife was forced to continue the payments, as the contract was over only when Jeanne kicked the bucket. She eventually shuffled off the mortal coil at the age of 122, and had been paid a total of over $180,000--twice what the apartment was worth.

John Fogerty Rips Himself Off (Twice)

The 5 Worst Deals In the History of Handshakes

John Fogerty was the singer, songwriter, guitarist and general creative force behind classic rock band and mom aphrodisiac, Creedence Clearwater Revival. Due to a falling out between its members (either Fogerty being a dick or an overworked genius, depending on who you ask), CCR disbanded in 1972. Which was a problem since Fogerty had been representing the band himself, and had signed them all to an insane 14-album deal. To give some context, the Beatles, in their long and prolific history, only produced 13 records. CCR had made six. Eventually the problem was resolved when Fogerty gave the rights to every CCR song to Fantasy in exchange for letting him leave the band, which is like resolving a roach infestation by giving the bugs your keys and moving to North Dakota.

The 5 Worst Deals In the History of Handshakes

That'll show 'em.

This meant that for the rest of Fogerty's life, he could never make money from, nor even play, the songs that he made famous; songs that still get airplay today. His ensuing solo career was pretty much what you've come to expect from "solo careers": A dismal downward spiral that ends in a Sambuca-flavored vomit puddle outside the wedding gig you're doing for "dibs on the buffet leftovers." Fogerty was understandably a little miffed at this whole thing, and recorded a scathing song called "Zanz Kant Danz" about the CEO who helped him screw himself over. In retaliation, Zaentz and Fantasy Records brought a plagiarism suit against Fogerty for infringing on one of the other songs they owned, called "The Old Man Down the Road." So who did John Fogerty allegedly steal this song from?

One Mr. John Fogerty.

The 5 Worst Deals In the History of Handshakes

Fantasy claimed that he ripped off one of his old Creedence tunes to use in his solo career, and since they owned the entire catalogue, they decided to bring him to court. And while the justice system, proving it wasn't completely insane, eventually upheld Fogerty's right to take inspiration from himself, he did have to change the title of his other song to "Vanz Kant Danz," doubtlessly confusing many fans as he apparently penned a scathing rock retort to a shoe company.

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For more people who would be envious of these deals, check out The 5 Ballsiest Con Artists of All Time. And find out what their apologies would be on par with, in The 6 Most Insincere Apologies of All-Time.

And stop by our Top Picks (Updated 06.09.10) to see the deal Popsicle Pete made with satan.

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