Smugglers, Bootleggers, and other Scoundrels


Thanks to the Gutenberg Project

The subject of smuggling is interesting, instructive, and not confined to any one country, region, or culture.  People are — who they are, and none of the folkways of a particular people change simply because they uproot themselves and travel to another settlement.  Long before the first person from Great Britain traveled to North America, the British ignored any law their king or parliament imposed upon them that they regarded as disagreeable or unjust.  One might argue, therefore, that smuggling has been a regular consequence of government tyranny.

Of course, governments impose taxes to pay for things government leaders believe are essential or most desired.  Paying for wars is generally at the top of this list, or in the modern day, paying for social services as part of the notion of redistributing wealth.  If people believe such taxes are onerous, unfair, or unwarranted, the taxed will likely rebel in some form or fashion.  They will refuse to pay the tax or lie about how much of a taxable item they possess, or they may find ways to avoid the tax altogether.

The problem began when European powers attempted to establish coherent imperial economies and sought ways to control the trade of their own (as well as foreign shipping) while expanding state revenues through taxation.  During most of the 16th to 18th centuries, ambitious attempts to constrain, delimit, or monopolize specific areas of commerce were rarely bolstered by sufficient power to back up those policies.  There were never an adequate number of customs agents — and, in any case, the government’s expenses in imposing taxes quite often exceeded revenues produced from enforcing such policies.


Early modern smuggling is connected in many ways to the history of state regulations of commerce, what historians once called “mercantilism.”  Smuggling could consist of illicit trade within a particular state to avoid paying taxes and duties, trading in goods controlled by monopolies (or “interloping”), or trading in outlawed goods.  Smuggling also included inter-imperial contraband involving many parties.  It was common to find Spanish customs agents willing to accept bribes for looking the other way and sea captains from numerous countries willing to offer those bribes — even when such transactions involved traditional or long-time enemies.

As with most illicit activities, there are not many records to document what happened, when, or the names of individuals involved — otherwise, such records might become evidence of the existence of the world’s worst smugglers and lawbreakers.  This dearth of information forces historians to speak of “informal” economies rather than smuggling operations because smuggling was but one illicit activity — and there were several.

As for smuggling, such activities required complex networks of human activities.  There had to be people who served as lookouts; others had to load ships, others to unload them and carry goods to shore.  There had to be a place to store smuggled goods until they could be collected.  Someone had to maintain records of transactions and do it in a way that government agents or investigators could not easily decipher.  Last but not least, there had to be some way in which smugglers could hide or disguise their ill-begotten incomes.

The sole purpose of some settlements in the West Indies was to smuggle goods in and out of such places as France, England, Scotland, Ireland, and Spain.  The Dutch-owned island of Sint Eustatius is but one example of many.  The Danes had a well-oiled operation smuggling sugar through Saint Thomas and Saint Croix.  The Brandenburg Company smuggled slaves to New Spain.[1]  After 1833, the slave trade became illicit, which increased the cost of slaves to those who used them. 

The sole purpose of several Atlantic settlements, especially in the West Indies, was for smuggling goods in and out of empires, like the Dutch island of Sint Eustatius.  The Danes also smuggled goods like sugar through their islands in Saint Thomas or Saint Croix, and the Brandenburg Company was involved with smuggling slaves into New Spain.

Illicit trade could go on seamlessly with the compliance of local administrative officials — and there has never been a lack of corrupt officials.  And, in any case, some historians note that one nation’s smuggler is another nation’s legitimate merchant. 

The Role of Salutary neglect

The word mercantilism refers to an economic system of trade that existed between the 16th to 18th centuries.  It was based on the principle that the world’s wealth was static, and governments had to regulate trade to build wealth and national power.  Due to the nationalistic nature of mercantilism, nations frequently used military and naval forces to protect markets and natural resources.

The British policy of mercantilism set the stage for imperial regulation of colonial trade policies.  Mercantilism prioritized the financial growth of the British crown and controlled colonial economies.  In the 17th century, the British government demonstrated control and placed formal trade restrictions on the American colonies, known as the Navigation Acts.  In 1651, the first of the Navigation Acts targeted Dutch competitors and forced all British-colonial shipments into British-owned ships.  Later iterations of the Navigation Acts implemented regulations on trading specific goods such as wool, sugar, indigo, and tobacco.  The British benefitted by taxing vessels arriving and departing from English ports but hindered national profit by forcing people to avoid taxation through smuggling schemes.

The essence of salutary neglect was that the parent (mother country) sought to encourage productivity from the petulant child (colonies) by turning a blind eye to illicit trade activities.  As much, previously mentioned, enforcing trade laws was an expensive proposition — for every shilling paid to a customs agent, there was one less shilling deposited into the national treasury.  Turning a blind eye to illegal activity did increase individual freedom of action in matters pertaining to trade and self-government, and it did result in colonial growth and prosperity — until the British government needed money to pay for disagreements with foreign competitors.  The British treasury was nearly empty at the end of the Seven Years’ War (which included conflicts with several European countries).  Salutary neglect suddenly came to a screeching halt, and the Colonists decided they were unfairly taxed.  The Americans wanted the British Army to protect them from French and Indian marauders — they just didn’t think they should have to pay for it.

Luckily, the American colonists had been smuggling goods for more than 100 years; they knew how to do it (mostly) without getting caught — and it was a skill set they would need between 1776 – 1783.

American Attitudes

The attitudes of Anglo-Americans didn’t change simply because they shucked off one government for another.  In 1789, Congress was pleased to announce the new United States of America, founded on a constitution restricting government to only a few enumerated powers (over the people).  And to sweeten the deal, Congress agreed (after much debate) to offer the people a Bill of Rights.  Previously, under the so-called Articles of Confederation, the central government could not raise taxes, severely limiting the government’s ability to spend money.  In effect, if there were to be any government spending, it would have to be passed along to the states to pay their “fair share.”

The Revolutionary War required Congress to borrow money to pay for it.  At the war’s end, Congress had accumulated $54 million in debt, and state governments had amassed an additional $25 million.  Alexander Hamilton (formerly a West Indies tradesman and smuggler) devised a scheme to use this indebtedness to develop a national financial system that would promote prosperity and national unity.  He succeeded in doing that.  He united nearly every American around the fact that they hated paying taxes to the U.S. government as they did to the British parliament — which was revealed in 1790 when Congress passed an excise tax on whiskey production.  Nearly everyone who made distilled spirits agreed, but everyone who ever thumped a bible lined up in favor of the “luxury” tax.

The population of Western Pennsylvania in 1790 was around 17,000 people.  Pennsylvania farmers relied on whiskey production to supplement their meager incomes.  Complicating the matter in 1790 is that money was in short supply … and more often than not, people bartered with one another.  Whiskey was often traded for other goods.  For Congress to impose a tax on whiskey made it an “income tax” rather than an excise tax.[2] 

Initially, people who opposed the Whiskey Tax petitioned the government to repeal it.  Several conventions met to discuss the matter in Western Carolina and Pennsylvania.  That didn’t work, of course, because the United States was in debt and needed to raise money to reduce it or pay it off.  Unfortunately, Mr. Robert Johnson of Washington County bore the brunt of the citizen’s unhappiness when he was tarred and feathered and “run out.”  Mr. Johnson’s attackers were ordered to appear in court, but they refused.  When whiskey makers learned that the government was serious about the tax, they ran for their guns, determined to resist any effort to force payments.

In this instance, nothing had changed since the Malt Tax imposed on the Scots 66 years earlier — with amazingly similar results.  The Whiskey Rebellion was only this: the continuation of the long-established American bootlegger movement — and one that continues to this very day.

One amusing story from the 1920s involved a fellow known as The Man in the Green Hat.  According to The Washington Post, an underemployed veteran from World War I named George Cassiday turned to selling and transporting illegal alcohol during the Prohibition period.  From 1920 – 1925, George sold illegal whiskey to members of the House of Representatives when the House was in session, and business was so good he found himself hustling from one congressman’s office to another from around 9 a.m. until quitting time.  According to the article, Cassiday transported between 35-40 quarts of whiskey daily by train from New York, concealed in two large suitcases.  House members were so grateful for his libations that they even provided him with an office in the basement, from which he would make his deliveries.

When Capitol Police discovered the illegal activities, they arrested Mr. Cassiday and sent him to court.  He paid his fine and acknowledged the court order that he be forever banned from the U.S. House of Representatives.  The story made Cassidy nationally famous — so much so that he moved his operation to the U.S. Senate through 1930.  In comparing the two operations (House vs. Senate), Cassiday indicated that the Representatives were nicer people.


  1. History, Art & Archives.  United States House of Representatives, Historical Highlights 1901 – 1950.  Online Resource.
  2. Karras, Alan L. “Smuggling and Its Malcontents.” In Interactions: Transregional Perspectives on World History. Edited by Jerry H. Bentley, Renate Bridenthal, and Anand A. Yang, 135–149. Honolulu: University of Hawai’i Press, 2005.
  3. Klooster, Wim. “Inter-imperial Smuggling in the Americas, 1600–1800.” In Soundings in Atlantic History: Latent Structures and Intellectual Currents, 1500–1830. Edited by Bernard Bailyn and Patricia L. Denault, 141–180. Cambridge, MA: Harvard University Press, 2009.
  4. Mancke, Elizabeth. “Empire and State.” In The British Atlantic World, 1500–1800. 2d ed. Edited by David Armitage and Michael J. Braddick, 193–213. New York: Palgrave Macmillan, 2009.


[1] Archival Materials on the Brandenburg African Company (1682 – 1721), Adam Jones. Cambridge University Press, 1984.

[2] Excise taxes are taxes imposed by legislation on specific goods, such as motor fuel, tires, batteries, tobacco, and alcohol.

About Mustang

Retired Marine, historian, writer.
This entry was posted in Antiquity, British Colonies, Colonial America, History, Imperialism, Indenture & Slavery, Outlaws. Bookmark the permalink.

2 Responses to Smugglers, Bootleggers, and other Scoundrels

  1. Andy says:

    Americans have always looked upon taxes with distaste, and so they have endeavored to find ways to avoid paying them. As your article so aptly points out, one of the earliest ways to avoid these appalling taxes was by smuggling goods past government tax collectors straight to the consumers.

    Avoiding taxes is well and good as long as one looks at it only from the individual’s perspective. However, from the government’s perspective tax avoidance is anything but good because it decreases the government’s abilities to pay it’s just debts.

    Years of increased spending and decreased revenues have resulted in a national debt in excess of thirty trillion dollars. Interest on this debt is faithfully paid annually. It is estimated that the interest on the nation’s debt will reach one trillion dollars sometime in the next six years.

    I’m not advocate for increasing taxes or decreasing spending, both of which would help alleviate the economic dilemma we have created. Rather, I only hope to point out how far we’ve come since smugglers snuck that first cask of rum past the tax collectors.

    Mustang, I realize I’ve strayed somewhat off the topic you selected, and I hope you’ll overlook my discourtesy.


    Liked by 1 person

  2. Mustang says:

    There is no discourtesy, Andy. I enjoy reading your comments.

    I find the issue of taxes irritating for two reasons. First, I think that long before we discuss taxation, we should have a conversation about spending. I prefer the government hold itself to the same standard they assign to us as citizens: we can’t write bad checks and acquire more debt than our income-to-debt ratio will allow. When you and I served on active duty, we had to stay within our operating budget. In formulating an out-year budget, we had to prioritize spending. This standard should apply to the government as a whole. Once we decide what is necessary, we can talk about taxes supporting a balanced budget at some level.

    Second, taxation is one way we demonstrate that our states (and the people) are united. We belong to the same club. For about one-half of working Americans to be exempt from paying taxes, which places the entire tax burden on the shoulders of the other half, is, in my view, patently unfair and dis-uniting. Everyone should pay some tax. We can manipulate “how much” as a percentage of their income. BLS tells us that the average wage in the United States is around $1,041 per week ($54,132 per year). The poverty line is $35,801. Anyone making at or less than the poverty line should pay no less than 7% … so everyone pays something. Everyone belongs.

    That’s off-topic, as well. 😊

    Thanks again, Amigo.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.