Authors Note: These stories have been shared many times in the Cigar world. Now urban legends, a few are true, a few cigar smokers probably created it late one night. But then again, as a friend of mine says, “Never let the truth get in the way of a good story”.

Cigars and the Cuban Embargo…

The year is now 1962, and before President John F. Kennedy authorized a trade embargo with Cuba, he instructed his press secretary to acquire as many of his favorite Cuban cigars as he could find. Once the embargo was signed, Cuban products were no longer legally available to United States citizens. 

Cigar Crime Doesn’t Pay…

In Charlotte, North Carolina, a man with a passion for fine cigars figured out a way to get his smokes for free.  He purchased a case of 2 dozen very, rare, very costly cigars.  Like many people with objects of great value, he had them insured.  Nothing odd in that…except he had them insured against fire!  

It took the man less than a month to consume his stockpile, and although he hadn’t even paid a single premium on his new policy, he filed a claim with the insurance company.  He stated that his property had been lost “in a series of small fires.”  

Obviously, the insurance company balked, saying that the cigars had been consumed in a normal fashion. He called in his lawyers, they called in their lawyers.  He sued…and, much to everyone’s surprise, he WON!

In his ruling, the judge stated that the insurance company had issued a valid policy that warranted the cigars as insurable and guaranteed payment in the even of “loss by fire.”  The policy didn’t define an “acceptable” fire, so it was considered to be in force and the company was obliged to compensate the man for his “loss.”

Given the time and costs of a lengthy appeal, the insurance company felt it was more cost-effective to accept the judge’s ruling and paid $15,000 to their client for his “loss.”

But wait.  After our “hero” cashed his check, he was arrested – on 24 counts of arson!  The prosecution used the man’s own insurance claim and testimony from the previous case to prove that he had intentionally destroyed valuable property.  He was sentenced to 2 decades in prison – 24 consecutive l-year terms.

Or Does Cigar Crime Pay?…

The defendant in a lawsuit involving large sums of money was very concerned about the outcome of his case.  “If I lose, I’ll be ruined,” he said to his lawyer.

“It’s in the judge’s hands now,” his advocate explained.

“Would it help if I sent His Honor a box of cigars?” wondered the defendant.  

His attorney was horrified at the suggestion and urgently counseled his client against such behavior.  “This judge is a stickler for ethics. You shouldn’t even smile at him!  And sending him a box of cigars would completely prejudice him against your case. He might even find you in contempt of court  “

Two days later, the judge rendered a decision — in favor of the defendant. As the defendant left the courthouse, he said to his lawyer, “Thanks for the tip about the cigars. It certainly worked.”

“I’m sure we would have lost the case if you’d sent those cigars,” said the lawyer.

“But I did send them!” said the defendant.  “That’s how we won the case.  I sent the cheapest cigars that I could find and enclosed the plaintiff’s business card.”