Season 1, Episode 2 - The Birth of Bourbon, Part Two

Picking up where the previous episode left off, Brian & Lyman continue the story of how early migration in the United States led to the invention of bourbon whiskey. Listen in for stories of popular revolt, some of the many origin stories of bourbon, and even a secret agent tale.

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INTRO MUSIC

B: You’re listening to Episode 2 of Migration Nation with Lyman Stone and Brian Hudson, a Podcast about the history of migration in America. Lyman’s an economist and I’m a social studies teacher.
L: So for today’s episode, we’re picking up where we left off our history of bourbon and migration. We had just finished talking about the Scots-Irish in western Pennsylvania, and how the region was basically a powder keg in search of a spark.
B: And today, we’re going to watch that keg explode, and then we’re going to follow the shrapnel as it lands, curiously enough, in Kentucky. And then we’re going to talk about Spanish spies for a while because, seriously, this is history.

TRANSITION MUSIC

L: So it might help listeners if, before we get into the Whiskey Rebellion proper, we give them a sense of scale; like how big a deal is this rebellion anyways? I think we can answer that.
B: Sure, take it away!
L: Well, in all of western Pennsylvania, by which I mean the counties beyond the Appalachian mountains, there were probably about 75,000 European settlers. 65,000 of them lived in the five counties of southwestern Pennsylvania that we’re particularly concerned with here (that’s Westmoreland, Washington, Greene, Fayette, and Allegheny Counties). As we mentioned earlier, Pittsburgh had about 1,500 people living in it, and was definitely the largest urban center in the area. Now for comparison, Pennsylvania’s total population in 1790 is about 440,000 people.
B: That’s a actually larger proportion than I expected.
L: I know, right? Almost 15% of the state population in the west seems a little high. But by 1800, it rises to almost 20% of Pennsylvania’s population in the west. And if we had data for 1780, or for 1770, we’d probably see the population growing by a third or more each decade. Open land and comparatively easy access through the Monongahela Valley to Fort Pitt (later Pittsburgh) made the area as popular for early migrants as Kentucky would become in the 1790s. As we mentioned earlier, it’s actually these people who probably made use of the famous Conestoga wagons for their migrations.
B: So it’s an explosively growing population of untamed, ethnic minority, rural farmers, settling out on a violent frontier, far from centralized power.
L: What could go wrong!?

TRANSITION MUSIC

B: So, now that the stage is set for the Whiskey Rebellion.
In 1789, the ratification of the Constitution led to the formation of the national government we recognize today. Without going into too many details about the stark differences between this new government and the previous one under the Articles of Confederation, it should be known that the Articles had given Congress absolutely no power to levy taxes.
L: Which made some sense at the time, right? I mean, wasn’t centralized taxation basically the key reason we up and gave King George the boot?
B: Exactly. The Articles were reactionary that way. But it only took about a decade for the document’s weaknesses to make themselves apparent. So, in what our friends in western Pennsylvania probably would consider an overcorrection, the new Constitution gave significantly more power to the national government, including the ability to levy taxes. And levy taxes they did.
L: And I’m guessing they didn’t levy taxes on, like, maritime construction or something.
B: Nope. The big one was on whiskey.
So yeah, these generally Anti-Federalist frontierspeople were pretty averse to the idea of taxation by the national government in the first place. As you mentioned earlier, this IS in some ways for many of the same reasons that people distrust the national government even today. The capitol is hundreds of miles away, even across a mountain range! What do Alexander Hamilton and those fools in Congress know about life in The West, anyway? There’s a huge cultural divide between Fort Pitt and Philadelphia. Why should one get to decide the other’s laws?
L: Well but surely they understood that there had to be some taxes. Rebellious as they may be, I can’t imagine they were actually anarchists. Why’d they hate the booze tax so much?
B: Well the grand plan laid out by President Washington’s Treasury Secretary Alexander Hamilton for the US economy involved building credit by taking on all of the former colonies’ war debts from the Revolution. In order to help service that debt, Hamilton pushed Congress in March 1791 to pass a new tax on distilled spirits to replace an older one.
L: Wait. This was replacing an old tax? If there was already a tax on spirits before 1791, then why was this new tax so unconscionable?
B: Hold on. I’m getting there.
The old tax passed in 1790 was a tariff on imported distilled spirits based on quantity and alcohol content. These taxes on imported goods, though unpopular (it was still a tax, after all), were not worth getting too riled up over, especially in frontier areas where you’re not going to be importing that much liquor over the mountains. What really caused a fuss, though, was what Hamilton pushed into the 1791 act to increase revenues: an excise tax on domestically produced spirits.
THAT was unconscionable to our friends on the frontier.
L: Again, I gather they’d oppose it, but why unconscionable?
B: You know how I told you that those producing and selling whiskey could be expected to have earned cash, and therefore could be expected to pay taxes?
L: Yeah?
B: That expectation was totally off base, at least for the small distillers west of the Appalachians.
The reality was that, at that time, cash was very hard to come by west of the mountains. For a lot of these communities, the local economies functioned almost wholly on barter, and one of the most popular bartering goods in the West had been whiskey.
L: And I imagine Hamilton wasn’t just like, “Whoops, sorry, my bad!”
B: Whoops, indeed. Ever since those lands first opened up decades earlier and were flooded with Scotch-Irish migrants and their stills, whiskey had been fairly prevalent. Beyond the obvious reason for making whiskey, there was a real practical concern. Surplus grain was perishable and difficult to transport. It made much more sense to convert that grain surplus into whiskey, which didn’t spoil and was easier to store and ship.
This practice became even more prevalent during the Revolution. As William Findley put it:
“In the time of the revolutionary war, when neither foreign rum nor molasses could be imported, the demand for domestic distilled spirits for the army and for general consumption became exceedingly great, and the manufacturing of it became so profitable, that not only the rye, but a great quantity of wheat was consumed by distillation.”
Furthermore, in its role as a bartering good, it was pretty simple to trade a quart of whiskey for your family’s groceries rather than to have to bring a bunch of other sundry goods to the local grocer for barter.
L: Oh. So it’s basically an income tax for these folks… which as I recall is unconstitutional at that point.
B: Yes, and it’s a crypto-income tax that really only targeted poor western folk who might be produce this newly-taxed whiskey. And who doesn’t love the income tax?
L: Well yeah, so of course they hated it. It’s not just that it was a tax, it’s that it was a tax that specially burdened already struggling people, and endangered their basic ability to survive. I mean I’m sure failure to fork up the rare currency for taxes meant tax liens on land, and that means, like, total economic failure, full stop. And national leaders thought this tax was going to work in places where the people were basically already in a state of permanent unrest? Yeah, good luck with that.
B: Yup. A disaster in the making.

TRANSITION MUSIC

B: Now to give these westerners the credit that is often denied them, it’s important to mention that all hell didn’t break loose the moment the whiskey tax went into effect. It’s not often taught in history classes, but it should be noted that there was a lot of fairly moderate protesting and petitioning. Formal conventions were held to draw up petitions that would be sent to state and national lawmakers. And they did win a concession in 1792: the tax was reduced by one cent.
L: Well, that’s something at least.
B: Yeah, but I’m not sure that small distillers saw it that way. It was still a cash tax based on some theoretically sound, but realistically flawed, math of Hamilton’s, that truly threatened to put them out of the whiskey business altogether, if not in jail due to unpaid taxes.
L: Oh right, because any cash tax on whiskey was going to be hard for them to pay, regardless of level.
B: Right. Now although there were many moderates in western Pennsylvania who opposed the whiskey tax through the aforementioned petitions and conventions, there were also, as you might have guessed, many who expressed their discontent through more violent means.
L: One might say, untame means.
B: Un-tame indeed. As early as September 1791, a tax collector by the name of Robert Johnson was tarred and feathered in Washington County, Pennsylvania by a group of men who had disguised themselves as women. Then, the official who was sent to serve warrants on those involved was also tarred and feathered, and apparently also whipped.
L: So this sounds a lot like the American protests against British taxation.
B: It is. These are mostly kinda of like “genre” tropes for American popular revolt. But as the unrest continued, the coalition for moderation seemed to have less and less of a voice. And reading about these rebels, I really got the feeling that they fancied themselves spiritual successors to the Sons of Liberty.
L: Oh so not just a coincidental mimicry of those pre-revolutionary movements, but a conscious one?
B: Yeah. So there was a group called the Mingo Creek Association, a militant group that emerged and began to further radicalize the discourse among the opponents of the whiskey tax. These began raising “liberty poles,” setting up committees of correspondence to encourage other states to rebel, and positioning themselves as the primary judicial body in some areas. They did all this in addition to having taken over the local militia. This seems like a direct, and probably intentional, copy-catting of early American patriot movements.
L: And that also sounds like...escalation.
B: That’s what Alexander Hamilton thought too. At about this point in late 1792 he wrote up and had President Washington sign a proclamation condemning the rebellion in Western Pennsylvania.
L: I’m sure that didn’t escalate anything.
B: Well, basically a group of farmers file another petition, then, as they get more and more radicalized, 7,000 of them gather outside Pittsburgh, ready to march on the city and burn it to the ground.
L: What!? Seriously?
B: Yeah. And, in a fun twist, some of them start saying they want to declare independence and join Spain or Great Britain.
L: Uhhh… okay, so that’s kinda strange, because that issue will come up again.
B: Oh?
L: Yeah, No need to discuss here, but trust me, it’ll come up again.
B: Okay then. So eventually, Washington calls up some state militias. But so few men show up to enforce the deeply unpopular whiskey tax, they have to implement a draft. Which makes anti-Federal sentiment even more widespread. But one way or another, Washington gets his army of 13,000 men, a huge army for the time and considering western Pennsylvania had, as you said, only about 65,000 people total.
L: Yeah; that’s a demographically significant military force.
B: Which, by the way, we’ll come back to; there’s a fun side effect. But anyways, the rebels disperse before the army even arrives, and even most of the arrested leaders are eventually pardoned. Anti-draft protests eventually subside as well, and peace is restored to western Pennsylvania.

TRANSITION MUSIC

L: Sooooo okay... the Whiskey Rebellion is interesting and all, but what does all this have to do with migration?
B: Well, for one, the Whiskey Rebellion illustrates how even these early westward migrations over the Appalachian Mountains not only separated people geographically, but also culturally. The people beyond the Appalachians were creating a new kind of country. But maybe even more specifically, it’s because, in the wake of the Whiskey Rebellion, at least a few of the rebels fled even further west to preserve their “untame” way of life.
L: Ah yes, to the savage wilderness of Ohio.
B: (laughing) Uh, no. To Kentucky. Although there was already distilling activity in Kentucky before this, we know that some of these western Pennsylvanian Scots-Irish picked up and moved to Kentucky, where taxes were lower.
L: And they could be nearer a state capital.
B: Right, exactly. They could get redress of grievances. With the result that enforcement of the whiskey tax was always pretty hit-or-miss in Kentucky.
L: Why not just march an army out to Kentucky?
B: Well, western Pennsylvania wasn’t the only place to resist the Whiskey tax, or even necessarily the most violent. What it was was a rebellion within striking distance of the center of Federal power stretching from Richmond, Virginia to New York City. Plus, the state government of Pennsylvania was highly supportive: most of the troops Washington had were state militias.
L: Ah, so going to Kentucky would be harder, because the state militia wouldn’t be any help at all.
B: Right; and it would be an even further and more arduous march. The risk of failure, and thus a catastrophic loss of legitimacy for the Federal government, would be higher.
L: So Kentucky distillers manage to avoid the tax?
B: I mean, not completely; but yeah, Appalachia’s illegal distilling tradition goes back way before Prohibition.
L: Apparently.
B: Oh, I should also say, there’s also some historic attestation of another migrant group after the Whiskey Rebellion: deserters from Washington’s army.
L: Seriously? So it really was demographically significant!
B: Yeah. I mean think about it: a key limitation on migration, as we’ve discussed, was the cost. But if the government pays for your travel over to the far side of the mountains, the most expensive leg of the journey…
L: Then, yeah, you might just leave the army and keep going west. Don’t want to stay around your former compatriots or the people whose rebellion you were squashing, so you skip out to a promising new land, of which stories are told…
B: Kentucky.
L: Huh. You know, we’re gonna return to “military migration” several times in this series; but I didn’t expect to run into it already. But do we actually know this stuff happened? It seems like it could easily just be some mythologizing about bourbon’s roots deep in American history.
B: Well, the scale of Whiskey Rebellion-related migration is, it must be said, a complete unknown. Could be a couple dozen, could be thousands. But we do know that at least some rebels fled the area to Kentucky, expressingly in pursuit of a place to continue their libertarian way of life.
L: Oh?
B: Yes. The story of Captain John Hamilton is probably the best example. He was born in western Pennsylvania in 1766, and died in 1863, nearly 100 years old. His father was a Scots-Irish immigrant in the 1760s, who married another Scots-Irish immigrant in western Pennsylvania.
L: Okay, so we’ve confirmed the “Scots-Irish” bit. Apparently these people did exist.
B: So John is out on the frontier, with limited education. Allegedly, he learned to write his family’s name by writing it on the heads of whiskey barrels while distilling.
L: (laughing) Okay, so that sounds like mythology, but if that’s what the Scots-Irish are saying about themselves, then I think it doesn’t matter if it’s true or not.
B: What, you didn’t learn to write your name by inscribing it on whiskey barrels? Anyways, John Hamilton moves to Kentucky in 1785, where he continues distilling. When the Whiskey Rebellion breaks out, he goes back to the family farm in Pennsylvania to get in on the action.
L: Classic.
B: So he heads back to Pennsylvania, and finds the Federal army camped out on his family’s farm, since his brother had refused to pay taxes on his still, and hidden it away. So John Hamilton and his brother sneak out at night, retrieve the still from its hiding place, and hide it by some boats on the Monongahela River.
L: Sneaking distilling gear through Federal lines? This is definitely a story about Irish people.
B: Scots-Irish! There’s a difference. Anyways, a few days later, a friend brings some canoes and they head down the river to Maysville, Kentucky, and then into Old Bourbon County, where they start distilling again.
L: Wow. Okay. So we have explicit evidence of at least some Whiskey Rebellion participants packing up, fleeing the Feds, and moving to Kentucky to distill their product.
B: Yeah. This is the real deal. And that, finally, brings us to bourbon.

TRANSITION MUSIC

B: So some of the early distillers in Kentucky didn’t just share cultural affinities with their rebellious Scots-Irish brethren in Western Pennsylvania… they were actually the same distillers. And arguably, the vigorous response to the Whiskey Rebellion in Pennsylvania played a significant role in leading to the geographic center of distilling moving west, into lower-taxed, harder-to-police Kentucky.
L: Which gets us, finally, to bourbon.
B: At long last!
L: No kidding.
B: So we’ve said that immigrants from Scotland and Ireland, and especially the Scotch-Irish from around northern Ireland and southwestern Scotland, had a native culture of distilling. But that might take some explaining. See, the word whiskey actually comes from an old Irish word which means… well… and I know this fulfills all your stereotypes about my people Lyman… the Irish word from which whiskey is derived means… water.
L: (laughter)
B: Okay, so, yeah, that seems to tell us a lot. But distilling was used because water was often dirty, while whiskey and gin could be produced in plenty, fairly cheaply, and they were sanitary. Plus, for the often poor Irish, it was a good source of more calories.
L: Just, you know, with the minor side effect of alcoholism.
B: Right. And in a well-known story, alcoholism gets so bad in Ireland that Arthur Guinness invents his Guinness beer to create a healthy alternative to distilled spirits.
L: Now, when is that?
B: In the 1750s… so right when the Scots-Irish are starting to migrate to the United States. In other words, distilled spirits were so prevalent in the culture from which Scottish, Irish, and Scots-Irish immigrants came, that social reformers were trying to encourage beer consumption as a positive reform.
L: Okay. So these people brought distillation with them. But not all distilled beverages are bourbon.
B: No. For that, we have to get into some, let’s say, mythological history.

TRANSITION MUSIC

B: Around 1782, a minister named Elijah Craig migrated to Georgetown, Kentucky. He’d been jailed several times in Virginia for illegally preaching the doctrines of what was then seen as a fairly radical Christian sect: baptists. He was following his brother, Lewis Craig, also a baptist minister who’d suffered persecution. Lewis had led 600 fellow baptists to Kentucky in 1781, and this group settled in Kentucky even as the western battles of the American Revolution were fought around them; and, indeed, they fought on the side of the revolution.
L: Woah woah, we’re talking about how bourbon came to be. Baptists, my friend, do not drink.
B: Maybe not anymore, but they sure did back then. By 1789, Elijah Craig sets up a distillery and, allegedly, begins storing his whiskey in white oak barrels.
L: Oh, well, okay then. So Elijah Craig, a baptist minister fleeing religious persecution in Virginia, invented bourbon!
B: Not so fast! Several bourbon historians, and yes we have bourbon historians in Kentucky, doubt Craig as the inventor. The first source identifying him as bourbon’s inventor is in 1874. Plus, merely being in white oak barrels does not bourbon make.
L: Well, sure. It’s gotta be aged, it’s gotta be mostly a corn mash, and they’ve gotta be never-before-used, charred oak barrels.
B: Right. And though some sources say Craig’s barrels were charred, it’s not unanimous. And we know little about how much he was aging his whiskey, or whether it was mostly corn.
L: Okay so… Elijah Craig didn’t invent bourbon?
B: It’s hard to say. Like Boone, he’s kind of a mythical figure. He’s also credited with Kentucky’s first paper mill, fulling mill, ropewalk… our first language, code of laws, irrigation, musical harmony, weights and measures…
L: Okay okay, I get it. Craig allegedly invented everything in Kentucky. But if not Craig, then who?
B: Well, some reports say a Revolutionary War hero named James Wilkinson---
L: (bursts out laughing)
B: What?
L: Um, okay, we’ll come back to James Wilkinson. But whatever you’re about to say, I guarantee you, James Wilkinson did not invent bourbon.
B: No?
L: No. I 100% guarantee it. We’ll talk about why in a bit.
B: Okay then. Well, a relative of Daniel Boone, one Wattie Boone, was distilling in the 1770s, almost certainly corn, likely using the plentiful white oak in the area. So Wattie Boone is a reasonable candidate, but we don’t know about the aging and charring.
L: So, indirectly, we can maybe add bourbon to the Daniel Boone mythos?
B: Uhhh… not what I’m going for here. Probably a better candidate is Evan Williams, who started the first documented commercial distillery in Kentucky in 1783. Some other people distilling were Jacob Beam, Elijah Pepper, Robert Samuels, and a few others. And by the way, if you don’t recognize the names, I’ve just listed off the founders of most of the major bourbon brands you buy today, except for Bulleit, which is a newcomer.
L: Wait you mean that Jacob Beam… that’s Jim Beam? It’s been producing for over 200 years?
B: Sometime between 1780 and 1795, the Beam family bourbons we know today began to be commercially produced and sold.
L: Wow.
B: I know, right? Long history in these brands.
L: No kidding.
B: So this “Kentucky whiskey” or “western whiskey” started to have a distinctive brand, being lighter than Pennsylvania rye due to its heavy use of corn, which itself was due to Virginia promoting corn cultivation.
L: But it’s not called bourbon yet. Nor is it really the bourbon we recognize today.
B: No, it’s not. We know that by 1854, the word bourbon was being used, charring barrels was uniform, and corn whiskey was aged long enough to get color and taste from the barrels it was in: so, bourbon. And we know that at least some distillers had figured out the virtues of charring and aging by the early 1800s, when a French merchant tasted the product after shipping in New Orleans.
L: So… sometime between 1800 and 1854?
B: Well, if we want something more exact, we know that Dr. James Crow, a Scottish immigrant, was charring and aging his bourbon sometime between 1823 and 1845. He’s the first person who can be documented to use the modern process, and was a trained chemist, so it makes sense he would discover it. So if you want an exact name and date, go with Dr. James Crow, between 1823 and 1845.
L: Dr. James Crow it is then. But… we never explained how bourbon got its name?
B: Actually, I think you can probably give a better answer to that than I can, since it’s really all about trade.

TRANSITION MUSIC

L: Distilling begins in Kentucky in the 1770s, greatly expands in the 1780s and 1790s, and by the 1820s, we’ve more-or-less arrived at the modern conception of bourbon. But the process of developing the product “bourbon” doesn’t tell us how bourbon got its name.
B: And there are several competing stories about how that name came about.
L: Right. So, one is that when Kentucky was still a part of Virginia, after 1785, a large part of it was organized as “Old Bourbon County.” This area eventually formed 34 of Kentucky’s current counties.
B: Of which we have an infuriatingly numerous 120, because an old law required that, to facilitate easy redress of grievances, all people had to live within a day’s walk of their county courthouses. So there’s that frontier pre-occupation with isolation and redress of grievances again.
L: So this old Virginia “Old Bourbon” County did have lots of distilleries, and the Ohio River port of Maysville, founded in 1784.
B: And by the way, Maysville is where buffalo used to cross the Ohio River and beat a path south towards Lexington, which was known as the “Buffalo Trace.” See? More bourbon brands. They should really give us ad revenue.
L: If only! So the story goes that bourbon barrels shipped from Maysville were labeled “Old Bourbon”, based on their origin. And that might be true; it does make some sense, as Kentucky whiskey exporters selling a distinctive product would have wanted to make sure buyers knew it was distinctive: so might label it that way.
B: Like many brands do today: looking at you, Maker’s Mark.
L: But there’s another story I like better.
B: Oh?
L: So if bourbon didn’t get it’s name from its origin, it may have gotten it from it’s destination.
B: Where is this mythical land of bourbon you speak of?
L: Obviously, New Orleans. Bourbon Street. Even in the 1700s, Bourbon Street was a major market and warehouse district, where many Kentucky sellers stored their goods. Spain controlled the Mississippi River and, for a period of time after 1786, permitted Americans to sell their product downriver, a fact which made distilling in Kentucky vastly more profitable.
B: And the trip downriver would age and jostle the whiskey a bit too. You can actually get “boat-distilled whiskey” today, for a price.
L: Right. So it’s possible that whiskey arriving in New Orleans was labeled “bourbon” by the Francophone population there based on “Bourbon Street” where it was sold and stored… and because its light red color made it distinctive from whiskeys they imported from Spain or France.
B: Okay then. So bourbon gets its name either from its origin in Old Bourbon County around 1785, or from Bourbon Street in New Orleans, in 1786. I like thinking it’s New Orleans; that makes bourbon like the jazz of whiskey I guess. Just as distinctly American, too.
L: On the other hand, if bourbon is named for its origin, that makes “Kentucky bourbon” redundant: all bourbon is Kentuckian under that idea. So, take that Tennessee Whiskey. You may be chemically almost identical, but you’ll never be bourbon.
B: So I guess we’re not hoping Jack Daniels will sponsor us.
L: Guess not? But now that we’ve talking about bourbon being shipped down the Mississippi River to Franco-Spanish New Orleans, that actually leads us to hands-down my favorite character in this entire story.
B: More than Daniel Boone?
L: Absolutely.
B: And the sleigh-riding New Yorkers?
L: (laughing) Yes! This guy, this amazing character from American history, I find more interesting than even those noble migrants. His name is James Wilkinson, and he was probably the most successful traitor in American history, and almost single-handedly destroyed American westward ambitions.

TRANSITION MUSIC

B: Okay so, james Wilkinson. You mentioned earlier he could not be the inventor of bourbon. Now you say he’s Benedict Arnold on steroids or something. Who is this guy?
L: I’m not sure why he’s not more famous. Wilkinson was a fairly senior though by no means distinguished officer in the Continental Army during the War for Independence, where he served with Benedict Arnold, that much more famous traitor, before being reassigned as the Clothier-General of the Army.
B: Is that what it sounds like?
L: Honestly I tried to find out, and couldn’t find an explicit answer. I like to think Wilkinson, famous for his charisma, was like the chief fashion consultant for the Continental Army. But he resigned after a few years, apparently bored of his work. After some post-war feuding with both George Washington and Horatio Gates, Wilkinson eventually migrated to Kentucky. His military rank helped him win influence in Kentucky, as men of status were fairly rare in “the west” as Kentucky was viewed at that time.
B: So he comes riding in, the heroic Clothier-General of the revolution?
L: Pretty much, but it wasn’t just his rank. Wilkinson was famously charming and good-natured, with stories told of him convincing his numerous debt-collectors to lend him extra money, as well as his penchant for acting as a kind of country doctor to all of his neighbors. The man was a born politician.
B: Did he end up holding any public office in Kentucky?
L: Eventually, yes: he was elected as a delegate to several successive “constitutional conventions” for the area that would eventually become Kentucky. In the elections running up to those conventions, he famously, and ridiculously, incorrectly interpreted the meaning of the word “posterior” to mean “before,” as in, Kentucky shall declare independence “before” 1788. And that’s not just independence from Virginia: that’s independence from everyone. Wilkinson’s public platform was, essentially, that Kentucky should be its own country.
B: Wait, what? Surely no one took that seriously? I mean, I love the Commonwealth… but we’re kind of… landlocked?
L: It’s actually really hard to say how many people supported this idea. Maybe some did. And some Kentuckians may have just felt they’d get a better deal in the still-unstable United States if they joined as a fully independent state like Vermont, rather than submitted to central oversight. But for Wilkinson, the goal was something else entirely. The goal was to get Kentucky to secede and join Spain as an extension of Spanish Louisiana. And, once he was elected chairman of Kentucky’s seventh constitutional convention in 1788, he tried to get a vote to accomplish exactly that: annexation by Spain.
B: Woah woah woah, slow down, you just said a really crazy thing that I can’t believe I haven’t heard before. This guy fought in the Revolution to get independence from the British crown, but now he wants to be annexed by Spain? Did I miss something?
L: Right, it does take some explaining! The details are a bit hazy, but it appears that, by April 1787, Wilkinson was in quite a bit of debt; more than his charm could get him out of. So he came up with a daring plan: he would load up some cargo (including whiskey), head down the Mississippi River, and try to sweet-talk the Spainiards into giving him an exclusive monopoly on exportation of Kentuckian goods through the port at New Orleans. At that time, Spain mostly prohibited American shipping on the river.
B: Guy had stones.
L: No kidding! Along the way, he bribes his way through some Spanish checkpoints, then stays behind for a few days while his cargo goes on ahead. When his boat arrives in New Orleans, the Spanish officials are dissuaded from seizing it by merchants who knew Wilkinson was on his way, and who allegedly implied to Spanish officials that Wilkinson was so popular in Kentucky that seizing his goods could lead to an invasion by the Kentucky militia.
B: Was he actually that popular?
L: No. I mean, this was classic Wilkinson. When we first arrived in Kentucky, he allegedly posed as the representative of a Philadelphia mercantile company for months before he could find some local position for himself. But anyways, the plan worked, and Wilkinson’s goods were unmolested. And he spent a very pleasant few weeks in New Orleans, sold his goods and returned home.
B: Wait, that’s all?
L: Oh, he also formally, albeit clandestinely, renounced his citizenship in the U.S., swore allegiance to Spain, wrote a lengthy intelligence briefing for the Spanish crown about Kentucky, and laid the groundwork for a plot to bring Kentucky under Spanish domination.
B: (some kind of exclamation)
L: Yeah! And I think the best part is that we actually have his expatriation declaration from Spanish archives. It reads, and I’m quoting here:
“Interest regulates the passions of Nations, as also those of individuals, and he who attributes a different motive to human affairs deceives himself or seeks to deceive others: although I sustain this great truth, I will not, however, deny that every man owes something to the land of his birth and in which he was educated...Born and educated in America, I embraced its cause in the last revolution, and remained throughout faithful to its interest, until its triumph over its enemies: This occurrence has now rendered my services useless, discharged me of my pledge, dissolved my obligations, even those of nature, and left me at liberty, after having fought for her happiness, to seek my own; circumstances and the policies of the United States having made it impossible for me to obtain this desired end under its Government, I am resolved to seek it in Spain.”
B: And because he did this clandestinely… yeah, so, he’s just a spy, pure and simply.
L: James Wilkinson, Spy-Revolutionary extraordinaire! In his report to the crown, he summarizes his plan by basically saying that Congress doesn’t care about the interests of Kentuckian frontiersmen, and can’t respond to their grievances due to the long distance to the capital.
B: There’s that old problem again
L: Right! So Wilkinson says that if Spain makes a concerted effort (supported by local notables loyal to the Spanish crown who should of course be duly rewarded, ahem), then, and I’m quoting again here, “it is not out of reason that a man of great popularity and political talents, co-operating with the causes above mentioned, will be able to alienate the Western Americans from the United States… and throw those (Western Americans) into the arms of Spain.”
B: So he did all this for money?
L: Yes. Well, maybe not just for money. Wilkinson claimed to be acting out of “interest,” but not just his interest. He claimed, and may have really believed, that Congress intended to ignore and misgovern the western lands, keeping them poor and unpopulated, in order that the eastern states could maintain political hegemony.
B: So he’s changing negligence due to distance, to distance being a proxy for different political interests, leading to persecution.
L: Right; that’s what I was thinking when you mentioned it for Pennsylvania. Wilkinson likewise correctly noted that Kentucky’s prosperity depended on access to the Mississippi. In some sense, he may have truly seen himself as carrying on a kind of revolutionary cause: first for the American cause against Great Britain, and then for the Kentuckian cause against Congress. On the other hand, we also know that Spain paid Wilkinson thousands of dollars (so much so that he encountered logistical difficulties shipping all the silver coins back to Kentucky), and offered him large land tracts in Spanish Louisiana. So maybe he was just greedy.
B: Okay. So he goes back to Kentucky. But his plan fails, doesn’t it? I mean, Kentucky didn’t join Spain.
L: Right. It fails. For a moment, Wilkinson held the convention in his grasp, having delivered a long and impassioned speech about Congress’ neglect of Kentucky. Then Wilkinson yielded the floor to someone he believed an ally, a man who had also had correspondence with Spanish officials regarding navigation of the Mississippi. But this man, unbeknownst to Wilkinson, had split from others in Wilkinson’s faction due to disagreements about how Kentucky’s constitution should be written. So he gave only a timid and perfunctory comment instead of the rousing call to action he’d been assigned. Shortly thereafter, the momentum for independence collapsed.
B: So he failed. But I thought you said that he was successful?
L: Oh, he was! Wilkinson continues to correspond with Spanish officials for decades. He becomes the top American military commander from 1796 to 1798. And he’s still sending secret messages and intelligence to Spanish officials!
B: You’re serious here?
L: As a heart attack! America’s chief military commander was working as a spy for Spain, getting paid in clandestine shipments of, I’m not kidding, barrels full of silver coins.
B: (extensive laughter)
L: Yeah, and when the Lewis and Clark expedition sets out, Wilkinson sends a letter to the Spanish advising them to send patrols out to capture or kill the party: which the Spanish officials did in fact do, but the soldiers just failed to locate the expedition out in the wilderness. After that, Wilkinson urges the Spanish to strengthen their border defenses which, again, they do in fact do. When he’s made the senior officer of the army in 1800, Wilkinson again renews his relationship with Spain, receiving cash for information.
B: Holy cow. This is crazy.
L: Oh, the crazy has not yet begun. Eventually, Wilkinson gets involved with a guy named Aaron Burr.
B: (laughing) No! This is too wonderful.
L: Yes.
B: So he served under Benedict Arnold in the Revolution, and then…
L: And then he’s one of Burr’s co-conspirators in the plan to found a new nation out west. Apparently Wilkinson just wanted his own country: first America, then Kentucky, then a new country with Burr. And between Kentucky’s independence, trying to kill Lewis & Clark, and founding the nation with Burr, Wilkinson really didn’t think the US should spread out west.
B: No, apparently not!
L: So Wilkinson works with Burr to set up a new country carved out of Spanish territory in the southwest… then betrays him, passing along Burr’s letters to President Thomas Jefferson. It’s not totally clear why. Various officials bring charges against Wilkinson on multiple occasions, but he beats the rap every time. Nobody could ever prove he was a traitor, even though, by then, many people suspected it.
B: If he’s sending all these letters and getting all this money, how’s it so hard to prove? Surely someone could prove it?
L: Oh, I haven’t even gotten to the good part. Now we’re going to get to why Wilkinson is my favorite. Wilkinson didn’t go by the name “James Wilkinson” when we was doing spy things, oh no.
B: (eagerly) He had a codename!?
L: Yes! His codename, I kid you not, was Agent 13, based on a cypher system called the “Number 13” system. All of his letters to Spanish officials were sent in an intricate code that nobody could decrypt. Even though his coin deliveries were once intercepted, the boatmen were willing to testify against him, but the judge didn’t speak Spanish. So the judge called for a translator, one Thomas Powell, who…
B: Wait, no, you’re kidding.
L: Was also a Spanish spy! So he just lied about what the men were saying.
B: This is insane.
L: Wilkinson will even end up becoming the first Governor of the Louisiana Territory before being removed for abuse of power. Then he’ll be sent as the U.S. envoy to Mexico during the Mexican Revolution. There, he abuses his official role in order to petition the Mexican government for a land grant in Texas (much like Houston and Austin). In 1825, he died in Mexico City, aged 68. In 1854, enough of his personal correspondence was put together by biographers to figure out that, yes, he was definitely a traitor, which basically everyone had long suspected, but could never prove. Theodore Roosevelt later commented that, “In all our history, there is no more despicable character.”
B: Wow. So he literally spent his whole career spying for Spain from positions of serious influence, making repeated attempts to get his own little empire… and never got caught.
L: Right. Perhaps the best epilogue to his story are the few verses of poetry he selected to begin his memoirs, from the 18th-century play “Barbarossa.” They read:
“Remember that the ways of Heaven,
Though dark, are just: that oft some guardian power,
Attends unseen, to save the innocent!
But if high Heaven decrees our fall--O let us
Firmly await the stroke; prepared alike
To live or die.”

TRANSITION MUSIC

B: Wow. So the debate over how the new settlers in Kentucky should market their produce, including their increasingly popular “red liquor” eventually called bourbon, was way more involved than I thought.
L: But it does show some key dynamics in the early settlement of the west. Nobody quite knew how the nation was going to fit together, or what the final pattern of governance should look like. In some cases, a few people making a daring, gutsy move, like bribing your way down the Mississippi, could have had some really remarkable consequences.
B: We never did quite resolve where the name “Bourbon” comes from.
L: No, but that’s not the point, right? Ultimately, attempts to carve out numerous countries from the American west fail: first with Wilkinson, then with Burr. Future states like the Texas or California Republics are more successful, but still ultimately short-lived and aimed towards annexation. It’s actually quite remarkable that, for all that the original colonies were quite divided, the westward expansion of the nation is marked by extraordinary resilience in unity.
B: Even from the earliest migrations, isolated settlers mostly viewed themselves as part of an American project. I mean Wilkinson’s plan didn’t fail because of a fluke, right? It failed because most of the delegates in Kentucky didn’t want to declare independence. They wanted to be part of the union. They wanted to be Americans, just Americans in the west.
L: And thanks to that commitment, as well as the multi-lingual hodge-podge of New Orleans, and the rebellious migrations of Scots-Irish settlers, and the warlike expansions of Daniel Boone, we’ve got that most distinct of American whiskies: Kentucky bourbon.

TRANSITION MUSIC

B: Well, that’s it for the second episode of Migration Nation! Thanks for listening in, and we hope you’ll join us again. If you’d like more information about what we’re doing here, or would like to offer us your support, join us on the web at migrationpodcast.com, where you can find transcripts of our episodes, bonus nerdy materials from Lyman and me, and even a look ahead at episodes we have in the works.
L: If you want a really interesting account of James Wilkinson’s life, you might try Andro Linklater’s “An Artist in Treason: The Extraordinary Double Life of General James Wilkinson.” It’s the most recent account, and I relied on it, alongside several other sources, for much of the narrative of our villain’s life.
B: We also made heavy use of the historical information from the Distilled Spirits Council of the United States. So if you want to know more about the history of whiskey and bourbon, you can check out their website.
L: We hope you’ve enjoyed learning about the early years of American migration with us! Until next time, this is Brian and Lyman at Migration Nation, saying “Stay classy, migration nation!”

RUTH’S SUMMARY JINGLE


Music Credits:
Antonin Dvorak - "New World Symphony"
Al Jolson - "My Old Kentucky Home" under CC BY-NC-ND 3.0 US
The Joy Drops - "Not Drunk" under CC BY 4.0
Vernon Dalhart - "The Alcoholic Blues" under Public Domain Certification
Arthur Collins and Byron G. Harlan - "On my way to New Orleans" under CC BY-NC 3.0 US
Brian Boyko - "Folk Song" under CC0 1.0 Universal
Brian Boyko - "Born Barnstormers" under CC0 1.0 Universal
Anonymous - "Cheap Arp Guitar" under CC0 1.0 Universal
Doctor Turtle - "Let's Just Get Through Christmas" under CC BY 4.0