Stories Of Malicious Compliance That Exposed Legal Loopholes

Voting Rules
Vote up the sneakiest loopholes

Loopholes are a funny thing, aren't they? On the one hand, we can give kudos to the people that discover them. On the other hand, loopholes still have an overall feeling of being pretty questionable, right? When the word that most accompanies "loophole" is "exploit," you know you're working pretty squarely in the gray area. 

This then opens the door for fascinating examples of legal loopholes throughout history. This includes the likes of billionaires smuggling sporting teams away in the middle of the night, to a retired couple who outsmarted the state lottery system. Even America's beloved national parks aren't safe from the threat of a legal loophole. 

So let us know what you think of the folks responsible for gaming the system. Do you agree with these loopholes?

Photo: Sang Hyun Cho / Wikimedia Commons / CC-BY-SA 4.0

  • A Grape Juice Company Found An Ingenious Way To Get Around Prohibition
    Photo: Fruit Industries / Wikimedia Commons / Public domain
    539 VOTES

    A Grape Juice Company Found An Ingenious Way To Get Around Prohibition

    The Volstead Act (or National Prohibition Act) forbade the selling of alcohol in the United States in 1919 - but that was hardly going to stop the more inventive citizens from their favorite tipple. 

    One of the best tongue-in-cheek responses to the prohibition came from Vine-Glo, a company that sold grape bricks. Grape bricks on their own sound a bit odd, right? What would one use these for? 

    Well, Vine-Glo made sure to specify exactly what not to do on their label, including a warning on the box that read

    After dissolving the brick in a gallon of water, do not place the liquid in a jug away in the cupboard for twenty days, because then it would turn into wine.

    And to push the envelope just a little further, Vine-Glo also added what flavor the accidental wine would taste like: burgundy, sherry, port, claret, riesling, etc. 

    Perhaps the most entertaining aspect of this charade was that due to a loophole in the Volstead Act itself, making wine at home was, in fact, legal. (Up to 200 gallons a year anyway.) But we appreciate the sense of humor of Vine-Glo nonetheless. 

    539 votes
  • 2
    563 VOTES

    A Retired Michigan Couple Gamed The State Lottery And Won $26 Million

    When most people retire, they plan to slow things down. Not Jerry and Marge Selbee. Instead, the couple found a loophole in a lottery game - and won $26 million over a nine-year period. 

    It first happened in 2003, when Jerry realized Michigan's new lottery game, Winfall, had a severe miscalculation. Without going into the math, Jerry figured out (in a matter of three minutes) that if there wasn't a jackpot winner, the “smaller” winners were all paid out much bigger earnings. So, it became pretty rudimentary math to secure an almost foolproof payout (of between 60-80% of their investment.)

    After testing their theory - and finding out it worked! - Jerry and Marge started recruiting their friends and neighbors from their small town. At one point, they had 25 ‘investors’ - each of whom got a very healthy return. One friend said:

    It helped me put three kids through school and one through law school. So it was quite beneficial to me.

    Although Michigan shut the lottery game down (due to a low number of sales, ironically) some of the Selbee's investors realized Massachusetts had a similar game. So, a few times a year, the retired couple would drive 900 miles, buy hundreds of thousands of tickets, and go through them by hand in a room at the Red Roof Inn. 

    Nine years of gaming the system earned a hefty profit of $26 million.

    563 votes
  • 3
    432 VOTES

    An Inmate Technically Got Away With Murder Using The ‘Make My Day’ Law

    If you name a law after a Clint Eastwood line, you’re really just asking for it to be applied in screwy ways. The Colorado law allows a person to use lethal force to defend one’s dwelling if they reasonably believe an intruder could hurt them. 

    In 2011, Antero Alaniz, an inmate in at the Sterling Correctional Facility, killed a fellow inmate who entered his cell uninvited. The law was successfully invoked to grant Alaniz immunity from prosecution and has since been held up on appeal.

    432 votes
  • 4
    407 VOTES

    The Owner Of The Baltimore Colts Moved The Team To Indianapolis In The Dead Of Night To Avoid A New Law

    If you're a football fan, and you hear “the Colts” you probably think “Indianapolis” - the team's home base. However, you might also think ‘Baltimore’ - since that's where the team was stationed until 1984. 

    And the Baltimore Colts were pretty good. So good that they won the Super Bowl in 1971. And they had a loyal, passionate fan base.

    However, their luck started to turn after being bought by the hot-headed Robert Irsay. While the team maintained a few good years, their winning statistics tanked by the late ‘70s. Despite this, Irsay asked the city of Baltimore to pay for renovations at the Colts’ stadium. While it's unclear how the discussion went, it got to the point where Irsay started threatening to take the beloved team elsewhere. 

    This infuriated the locals, so much so that the Maryland governor signed a bill that the Colts would become the property of the city of Baltimore through eminent domain. Irsay somehow caught wind of this bill the night before - so, he hired movers to move the team offices to Indianapolis, where he had secured a late-night agreement for the team's new home. 


    407 votes
  • A Squatter Occupied A Home For Eight Months After Paying Just $16 In Filing Fees
    Photo: Inkani~commonswiki assumed / Wikimedia Commons / Public domain
    306 VOTES

    A Squatter Occupied A Home For Eight Months After Paying Just $16 In Filing Fees

    Squatting - the act of occupying an empty home or lot - has gained more followers as the housing market has become increasingly unreasonable for many Americans in the last few years. 

    One man, Kenneth Robinson, decided to take squatting to the next step. Robinson learned that a suburban Texas home (valued at $340,000) was abandoned, and the mortgage company went out of business. Robinson decided to use a loophole in adverse possession laws - which were put in place to keep abandoned homes maintained. 

    Robinson claimed that submitting the $16 filing fee allowed him to take possession of the home. 

    The brazen move created a media circus and a reaction ranging from grudging admiration to outright fury by the neighbors. In the end, a judge ruled that Robinson couldn’t stay, and the laws around adverse possession were strengthened in response. However, Robinson did get essentially eight months of free rent when all was said and done. 

    306 votes
  • 6
    310 VOTES

    McVities Won A Lengthy Legal Entanglement Over Jaffa Cakes Being Classed As Cakes

    Under British tax laws, cakes are a staple food while biscuits (cookies to our American readers) are luxuries - so the status of the popular snack Jaffa Cakes was a serious legal matter. 

    The British government contended their small size made them biscuits, while their manufacturer, McVities, insisted they were cakes. The case’s outcome rested on the company’s argument that when biscuits go stale, they soften - while stale cakes harden. 

    The hardened jaffas cracked the government’s cakes and allowed McVities to dodge a 20% tax on the roughly $1.4 billion in annual sales.

    310 votes