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Came across these urban legends regarding cigars and thought you all might enjoy them, true or not:

An urban legend is a kind of modern folklore consisting of stories often thought to be factual by those circulating them. The term is often used with a meaning similar to the expression "apocryphal story". Urban legends are not necessarily untrue, but they are often false, distorted, exaggerated, or sensationalized. Despite the name, urban legends do not necessarily take place in an urban setting. The name is designed to differentiate them from traditional folklore in preindustrial times. Any entity that is rich in culture and lore has the potential to fall victim to Urban Legends, these kinds of legends run rampant, passed down from generation to generation. We collected some good legends, and brought you those stories in order to show you new spots about the cigars culture.

JFK supply
As most devotees of cigar history know, President John F. Kennedy while not a fan of Fidel Castro was a great lover of Cuban cigars. And, according to many contemporary sources, Kennedy dispatched his press secretary, Pierre Salinger, to acquire as many of the president’s favorite cigars as he could before the landmark legislation was signed. Hence, Salinger was able to get his hands on 1,200 H. Upmann Petit Coronas, Kennedy’s favorite regular smoke. Tragically, he would not live long enough to enjoy all of those cigars, meeting his death at the hands of an assassin’s bullets in Dallas the following year. What many people don’t know - and what would probably drive them nuts - is that Kennedy actually attempted to have cigars exempted from the embargo! Richard Goodwin, a White House assistant to Presidents Kennedy and Johnson, revealed in a 2000 New York Times article that in early 1962 JFK told him, “We tried to exempt cigars, but the cigar manufacturers in Tampa objected. I guess we’re out of luck.” Indeed - as an entire generation of cigar enthusiasts eager to sample the island’s output remains out of luck today.

The Cigar Arsonist
Charlotte, North Carolina man, having purchased a box of 24 rare and very expensive cigars, insured them against... fire. Within a month, having smoked his entire stockpile of fabulous cigars, and having yet to make a single premium payment on the policy, the man filed a claim against the insurance company.
In his claim, the man stated that he had lost the cigars in "a series of small fires." The insurance company refused to pay, citing the obvious reason: that the man had consumed the cigars in a normal fashion. The man sued, and won.
In delivering his ruling, the judge stated that the man held a policy from the company in which it was warranted that the cigars were insurable. The company, in the policy, had also guaranteed that it would insure the cigars against fire, without defining what it considered to be "unacceptable fire," and so, the company was obligated to compensate the insured for his loss. Rather than endure a lengthy and costly appeal process, the insurance company accepted the judge's ruling and paid the man $15,000 for the rare cigars he had lost in "the fires."
However, shortly after the man cashed his check, the insurance company had him arrested on 24 counts of arson. With his own insurance claim and testimony from the previous case used as evidence against him, the man was convicted of intentionally burning the rare cigars and sentenced to 24 consecutive one-year prison terms.

The Virgin Cigars
South African cigar expert Theo Rudman addresses this hoary old legend in his on-line magazine. “It is a lovely idea,” he writes, “but alas is a legend that has persisted since the mid-forties, when a visiting journalist saw tobacco leaves being sorted and graded by women who placed the respective piles on their laps.” The visitor apparently took some imaginative journalistic license when he later wrote that Havanas were rolled on the thighs of virgins. Certainly, this story hasn’t hurt the mystique-laden marketing of Habanos.
“Yes, they would stretch the leaves on their uncovered skin, but to roll a cigar on one’s leg - you cannot do that,” Borhani says with a snicker. “I challenge anyone - man or woman - to put bunched tobacco on their thigh and roll a successful cigar.”

Delayed Gratification
Former President Grant is invited to speak at a graduation ceremony and, per tradition, he is given an honorary degree. He gives the Dean, an old war buddy, a cigar in return as a token of his appreciation.
A few weeks later Grant wires, asks him how he liked the cigar - and the Dean replies that he will keep it and treasure it, unsmoked.
The cigar is passed down from the Dean to his progeny.
Many, many decades later, (maybe 1980-something) a houseguest of a distant descendant of the Dean sees the cigar and, unfamiliar with its significance, lights up. It performs normally for a moment, and then explodes. Grant's practical joke finally gets played out, after something like 100 years. 

(There is similar UL attributed to FDR giving a loaded cigar to a university dean) 

Junk Collecting for Charity
Another cigar legend involves collecting junk as a way to contribute to charity. There was a time when hoarding wasn’t only reserved for the obsessive compulsive; in the olden days, people used to save all kinds of things - rubber bands, bags, tinfoil, and string. These people wouldn’t necessarily reuse the products they saved, instead they saved them for no obvious reason or reasons based on legends.
Cigar wrappers were soon one of these items that were religiously saved. In a sort of philanthropy gone awry, a myth was generated stating that people who saved cigar wrappers, cigarette packs, and the lids to coffee cans would be rewarded with devices needed for handicap people. It was rumored that 50,000 empty cigarette packs would get someone a hospital bed while 10,000 cigar wrappers would get someone a wheelchair. Though no one was ever able to cash in on their collection, this myth continued and junk manifested in the homes of those someday hoping their dedication to hoarding would pay off.

Urban Legends, like cigars themselves, come in a variety. Some are scary, some are believable, and some leave people afraid to eat pop rocks and drink soda at the same time. Cigar Urban Legends, though few and far between, provide people with a sense of tradition: they perpetuate the knowledge that cigars are always leaving their mark on us, forever burning their reputation into our culture.