Daniel Boone was a man. A real man. So the song goes.

I was Davey Crockett. It always happened that way because I was younger and had no say in the matter. My older sister, Julie, consistently played the part of Daniel Boone. She even got to wear the coonskin cap, which wasn’t really coonskin. They were baseball hats. But in the pretending of things, hers was coonskin, and mine was just some plain old hat. By her appointment. So it went.

I was better off, I think, even though Davey would end up dying at the Alamo. While Daniel Boone was a real trailblazer in his time, he was a bit of a screw-up in other matters.

First, let’s be reminded of the historical bend here. It was on this date, June 7, 1769, when Daniel Boone began exploring the Bluegrass State of Kentucky. But prior to and after that, a lot transpired.

The beginning in America happened in 1713, when his father, Squire Boone, came over from Bradninch, England. Squire chose Pennsylvania, founded by William Penn in 1681. Penn had established the place as one of religious tolerance, welcoming all. Apparently, the folks over in England were not so tolerant. At least, they didn’t care for Quakers, and Squire Boone was just that.

Squire, also a blacksmith and weaver, met and married another Quaker named Sarah Morgan in 1720. It wasn’t long until they were making Quaker babies — like eleven of them. Daniel was number six, entering the picture in 1734 in Berks County, Pennsylvania. They were living their happy little Quaker lives until two of the older Boone children married “worldlings,” or non-Quakers. If you marry a worldling, the Quakers kick you out of the club. It would appear they only seek religious tolerance for themselves. The two kids were disowned from the group, and when Squire Boone would not publicly apologize for his children, he was kicked out too. So they packed up all their belongings and moved by wagon to North Carolina.

We all know the story of Boone, exploring the state of Kentucky, and being a world-class frontiersman. The legends, while not all true, were things of legends. He explored the state, and in so, Boone was captured by the Shawnee for some time. They made him one of the tribe, and he married a nice Shawnee girl. But he was always looking to escape, and that is exactly what he did.

But while Boone was great at exploring the land, he was terrible when it came to owning the land. Maybe it was some kind of a Shawnee curse because Boone was unlucky when it came to real estate.

During the 1780s and 1790s, he worked as a surveyor in Kentucky while also investing in real estate. But this failed to make him rich. Boone ended up getting swindled in some deals, which surprises me. I guess meeting with some guy in a dark alley and buying a bridge was a bad idea for Boone.

He continued to muddle all his affairs, failing to properly register his land claims. He got hit with lawsuits for selling property to which he didn’t have a valid title. On top of that, he got sued for producing faulty surveys. His debts started adding up.

Boone tried some other things too. He owned a store and tavern in Limestone, which folded. He served as a supplier of ginseng root. Oh, but that ginseng market collapsed and left him in more debt. And then there was that time he bought those horses with the intention of reselling them. But wouldn’t you know it? Someone left the gate open, and all the horses escaped. By the late 1790s, Boone said he had soured on Kentucky and decided to leave. Or perhaps it the other way around?

In 1799, Boone moved with his family to present-day Missouri. He was in his mid-60s by then. Anyway, Missouri was under Spanish control. The Spanish government wanted to encourage settlement in the area, so they welcomed Boone with military honors and granted him 850 acres of land near St. Louis.

One year later, the Spanish ceded the Louisiana Territory to France, and three years later, the United States gained control of it with the Louisiana Purchase. Guess who lost his land again? Yes, Boone. He hadn’t followed the proper procedures to gain permanent title to the land.

President James Madison signed a bill into law in 1814, giving back Boone his 850 acres. But he had to turn around and sell all his property to pay off Kentuckians who’d heard the news about the gift. They traveled to Missouri to collect on old debts still owed by Boone.

So, there it is. He died in 1820 in Missouri, aged 85 years. A trailblazer with no business sense. We can’t all be perfect. In fact, none of us are.

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“The journey not the arrival matters.”
– T.S. Eliot

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“You cannot do kindness too soon, for you never know how soon it will be too late.”
— Ralph Waldo Emerson.

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“We are not rich by what we possess but by what we can do without.”
― Immanuel Kant

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