Good Try
A good shot but not eventually a real loophole was the “drink Pepsi, get a Harrier jet” guy.
In 1996, Pepsi ran a promotion where you could collect points by buying Pepsi products. The more points you got, the more stuff you could get, such as t-shirts, free Pepsi, sunglasses, etc. They also had a commercial where they advertised a Harrier jet for 7 million points.
One guy read the rules of the promotion and found that you could buy points for $0.10. That means to get 7 million points you’d have to pay $700,000. The going cost for a Harrier at the time was about $20 million or so.
So, one guy raised the money, bought the points and demanded the jet. When Pepsi refused he sued them.
He lost, but it was a good try.
Story credit: Reddit