“Loopholes” – the term originally used for slits on walls through which the master archers fired their shots at their enemy. However, the meaning that the term “loopholes” has taken over the years is no different. No system is ultimately perfect, and every system has its flaws. But when these flaws help exploit the system so much that the person doing it profits way more than anyone else, it is interesting to observe such a thing. Sometimes, when the system is a draconian or unfair one, we can’t help but root for the person exploiting the loophole. Here are the 10 times people exploited loopholes like a boss.

1 When the CEO of Apple Inc, Steve Jobs, realized that a leased car has a 6-month grace period before requiring a license plate, he went ahead and leased the same model of Mercedes Benz every six months to prevent requiring a license plate.

What better way to spell a unique personality than to evade a license plate on your car? Steve Jobs did exactly that. He realized that the vehicle laws in California only required a license plate for a new car within six months of purchase. Until then, it could be devoid of a license plate, and it would still be legal.

So, Jobs came to an understanding with the company and bought a new car, but the same model of the Mercedes Benz SL55 AMG, every six months and never got a license plate for his car.

However, it’s been some time since Steve Jobs passed away, and the California law has been changed only recently in the year 2019 to prevent any such loopholes.

Now, every car that is sold is required to be provided with a temporary license plate and is also supposed to be registered at the DMV. (source)

2 Kenneth Robinson learned of a 330,000-dollar house that went vacant and using a legal loophole of adverse possession, filed an application at court to live there at a measly compensation of 16 dollars. He stayed there for about eight months before being demanded by the court to leave the house.

Kenneth Robinson, a 51-year-old man from Texas, decided to take advantage of a loophole in the property laws which allows for someone to file for adverse possession when a house becomes vacant.

“Adverse possession,” also dubbed as “squatter’s rights,” is a law that allows for a non-owner to claim residence based on prolonged living in that property, without permission from the actual owner.

This happened when the owner of the house had abandoned the property, and it had gone to foreclosure. Furthermore, the mortgage company had gone out of business and was therefore unresponsive too.

However, the neighbors weren’t satisfied, and soon enough, the court claimed he was a squatter and escorted him out of the house, but only after he lived there comfortably for about eight months. (source)

3 David Phillips, a civil engineer from California, earned a whopping 1.2 million miles of airline travel through an offer that prompted him to buy a whole lot of pudding cups. Interestingly, he donated all the pudding cups to charity, making a profit for both himself and other people.

When there is an entire subplot in a movie dedicated to your actions, you are clearly of some importance. David Phillips, a Californian civil engineer, shot to fame with his ingenious method of earning traveler miles and inspired Adam Sandler’s character in the movie Punch Drunk Love.

The 1999 Healthy Choice promotion guaranteed 1,000 miles of free air travel for every 10 product barcodes mailed back to the company.

After speculating how to make the best of this opportunity, David decided to buy a whopping 12,000 pudding cups, each of which cost just 25 cents. The total cost came up to $3,140, and with 12,000 bar codes, he got a total of 1.2 million miles.

He donated the extra pudding cups too, which was another great feat. Interestingly, this is not the only time he did that as he continues to hack loopholes in a similar fashion to fund his love for traveling. He has taken some of his friends and family on trips across the world too. (source)

4 In the United Kingdom, a loophole in the legal system allows for the sale of unlicensed alcohol in moving trains. Taplin and Mageean Distilling, a company awaiting its license for alcohol distribution, was clever enough to benefit from them by setting up in an abandoned railway station, and selling gin to customers as the train moved back and forth.

The Taplin and Mageean Distilling, a gin distillery in Yorkshire, was waiting for its distribution license after being registered. However, one of its owners, Barry Mageean, who was studying “personal license” laws, found a loophole in the law that didn’t require a license for the sale of alcohol in a moving train.

They therefore sold and promoted their first batch of products on a moving train until they got their license.

On 7 December 2018, they designed a gin-tasting masterclass for guests in the two-and-a-half-hour journey this train underwent. The train started at the Leeming Bar, and the journey ended at Leyburn.

They also converted an old 200-year-old railway building in the Wensleydale Railway station into their packaging house from where they could easily transport the gin to the trains. (source)

5 In the year 1896, when the Raines law was passed to cut down on drinking alcohol on Sunday, the bars came up with an ingenious idea. The law only allowed them to serve alcohol with a meal. So, they served each drink with a sandwich, and then took it back and used the same sandwich for each order.

The Raines law, which was an excise law implemented to reduce public drinking on Sundays, required the bars to serve alcohol only with meals.

It was seen as hypocritical by the masses of New York because it prevented working people from having a good drink on their day off, while the rich were just left off the hook as they could drink and dine on any day they wanted to big hotels.

That is when the “Raines Sandwich” was invented. It was usually just a really bad sandwich with dried bread, some cheese, and ham.

The same sandwich would be passed on, even for weeks, between customers, as its only purpose was creating an illusion of being ordered as a meal only to be taken back by the bartender for later use to be served as a dummy meal for later customers.

This allowed for people to enjoy as many drinks as they wanted, with the Raines sandwich being tossed around from order to order, customer to customer, as a prop. (source)