In Lynchburg, Tennessee, tales of Jack Daniel are taller than Paul Bunyan on a step stool. The question is, are any of them true?

The legend of Jack Daniel reaches all the way back to the moment he was born. Unfortunately, nobody knows exactly when that was. Some records show that Jasper Newton “Jack” Daniel came into the world on September 5, 1846. His tombstone, however, says 1850. Strange, because his mother died in 1847.

All of this might not normally matter, but Jack’s birth date is important to his overall legend, which proudly proclaims him “the boy distiller.” So perhaps it’s best we begin when Jack was first introduced to whiskey, which we know was early in life. Leaving home at a young age, Jack struck out on his own with nothing more than a handful of items valued at $9. He ended up at the home of Dan Call, a preacher at a nearby Lutheran church and the owner of a general store. There, Reverend Call also happened to sell whiskey that he distilled himself.

Jack quickly became determined to learn the craft. In fact, many storytellers claim the boy wonder bought the still from Call and began pursuing the business full-time at the ripe age of 16. If that legend is true, then Jack began selling his own Tennessee whiskey only three years later; the famous black labels on the company bottles proudly pronounce, “Established and Registered in 1866.”

In reality, no documents support that myth. Jack may have been a teenage moonshiner, but he didn’t register his business with the federal government until 1875. And by then, Jack would have been the more booze-appropriate age of 29.

The Maker Makes His Mark

Whatever legends exist, one thing is certain: Jack Daniel had a brilliant mind for marketing. Even as a youngster, Jack understood that if people remembered him, they would remember his whiskey. To that end, he decked himself out in a formal knee-length coat, a vest, a tie, and a wide-brim planter’s hat, and was never caught out of “uniform” again.

Jack also established the Jack Daniel’s Silver Cornet Band—a 10-member outfit solely devoted to promoting his whiskey across the countryside. With uniforms and instruments from the Sears & Roebuck catalog and a specially designed wagon for traveling, Jack made sure the band played every saloon opening, Fourth of July celebration, and political rally around.

But perhaps Jack’s most brilliant decision concerned how to present his whiskey. From the beginning, Jack had been one of the first sellers to stencil his distillery name on his whiskey jugs. Next, he upgraded to round, custom-embossed bottles. But when a glass salesman showed him a prototype square bottle in 1895, Jack realized he’d stumbled upon something unique. The new bottles not only stood out from the crowd, but also had a shape that would prevent them from rolling around and breaking during transport. In addition, the square look reinforced the idea that Jack was a square dealer who put honest work and high standards first.

Whatever effort Jack Daniel put into his marketing, he never let quality slip. In 1904, the distiller decided on a whim to enter his whiskey in the taste competition at the St. Louis World’s Fair. It came as little surprise when he won.

Lucky No. 7

Perhaps Jack’s greatest coup was the name he gave his high-quality product—Old No. 7. Naturally, nobody seems to know why. The official historian at the Jack Daniel Distillery today says it’s the most oft-asked question on factory tours. As you might imagine, many theories have been advanced. Jack had seven girlfriends. Jack believed the number seven was lucky. Jack was honoring a merchant friend who owned seven stores that distributed Jack’s liquor. Jack misplaced a batch of whiskey for seven years and, upon finding it, labeled it “Old No. 7.”

None of these stories, however, makes as much sense as the less-than-sexy explanation from Jack Daniel biographer Peter Krass. Simply put, Jack was originally assigned a district tax assessment number of 7. But when the IRS consolidated districts within Tennessee, they arbitrarily reassigned him the number 16. Jack didn’t want to confuse his loyal consumers, and he certainly didn’t want to bend to the government, so he began labeling his bottles “Old No. 7.” More than 125 years later, this act of defiance still makes his labels stand out.

Jack Without Jill

Jack Daniel never married. Some say it’s because he was married to his work; others say it’s because he never found a girl who measured up to his high standards. Or perhaps it’s just that he was too busy catering to the greater Lynchburg population—throwing elaborate Christmas feasts, hosting exquisite costume parties in his second-story ballroom, and donating money to every church in Moore County.

But by all accounts, Jack was quite a ladies’ man. He was a perfect dance partner, a polite conversationalist, and a fantastic gift-giver. Unfortunately, he also gravitated toward girls young enough to be his daughter (or even granddaughter). Once, Jack even asked for a woman’s hand in marriage, but her father denied him—partly because Jack enjoyed keeping his own legend alive and always hesitated to reveal his true birth date. When Jack proposed, her father made it clear that any man unwilling to disclose his age was “a little too old for such a young girl.”

The Early Bird Gets the Gangrene

Hard as it might be to believe, in the end, the great distiller actually died from getting to work too early. As the story goes, one morning in 1906, Jack arrived at his office before anybody else. He tried to access the company safe, but had a terrible time remembering the code. After a few frustrating minutes, he kicked the safe as hard as he could. He badly bruised his left foot and immediately began to walk with a limp. The limp only grew worse with time, and he later discovered the injury had led to blood poisoning. Then came gangrene, then amputation, and then, five years later, death.

It’s not the happiest ending for the story, or the clearest cut, but it is the best, because it adds to the mystery and mystique of Jack Daniel. As they say, where facts cannot be found, legends fill the empty space—and that’s perfectly fine for the keepers of the company flame. After all, as Jack himself believed, the more memorable his image, the more memorable his whiskey.

This article was written by Eric Furman, and originally appeared in mental_floss magazine.