Argument

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How Filibusters Moved from Piracy to Congress

Freelance imperialists in the 1800s left behind weak institutions and racist legacies.

By , an assistant professor of political science at the University of Massachusetts Amherst.
Then-U.S. Sen. Strom Thurmond of South Carolina is mobbed by reporters.
Then-U.S. Sen. Strom Thurmond of South Carolina is mobbed by reporters as he leaves the Senate Chamber after ending his 24-hour, 18-minute filibuster against the civil rights bill on Aug. 29, 1957. Bettmann Archive/Getty Images

For most of this year, Washington, activists, and the national media have been gripped by the saga of whether the U.S. Senate filibuster will—or can—be eliminated. The requirement for a supermajority vote to cut off debate on most items of legislation has functionally transformed the Senate from a majoritarian body, in which 51 votes can rule, to one in which 60 votes are necessary to govern.

Discussions of the filibuster occasionally mention in passing that the word has another meaning. Historian Robert May noted earlier this year in the Hill that the word is derived from the Dutch vrijbuiter, which translates directly to “freebooter” and more loosely to “pirate.” And indeed, in the 1800s, the word “filibuster” became attached to illegal, pirate-like expeditions by American adventurers throughout Central America and the Caribbean.

The two meanings of “filibuster”—legislative and expeditionary—may seem coincidental. Conceptually, they are deeply linked. Both are coercive strategies employed by weak groups that can nevertheless cause outsized harms. Both undermine democracy and protect injustice—and were deeply linked to racism. And both have a legacy that includes not only the damage they have directly caused but the paths they foreclosed.

For most of this year, Washington, activists, and the national media have been gripped by the saga of whether the U.S. Senate filibuster will—or can—be eliminated. The requirement for a supermajority vote to cut off debate on most items of legislation has functionally transformed the Senate from a majoritarian body, in which 51 votes can rule, to one in which 60 votes are necessary to govern.

Discussions of the filibuster occasionally mention in passing that the word has another meaning. Historian Robert May noted earlier this year in the Hill that the word is derived from the Dutch vrijbuiter, which translates directly to “freebooter” and more loosely to “pirate.” And indeed, in the 1800s, the word “filibuster” became attached to illegal, pirate-like expeditions by American adventurers throughout Central America and the Caribbean.

The two meanings of “filibuster”—legislative and expeditionary—may seem coincidental. Conceptually, they are deeply linked. Both are coercive strategies employed by weak groups that can nevertheless cause outsized harms. Both undermine democracy and protect injustice—and were deeply linked to racism. And both have a legacy that includes not only the damage they have directly caused but the paths they foreclosed.


Filibustering in the expeditionary sense emerged in the aftermath of the U.S. expansion of the mid-1840s. The annexation of the Republic of Texas, hotly contested in U.S. politics, led to conflict with Mexico, which disputed Texas’s right to secede and the borders it claimed. In the ensuing war, the United States seizing more than half of Mexico’s remaining territory. Simultaneously, hard bargaining between the United States and the United Kingdom led to the division of the Pacific Northwest, a negotiation that averted war.

These were not minor irritants. Filibusters sought to seize parts of Mexico and Cuba, and one filibuster group even briefly secured U.S. recognition as the government of Nicaragua.

The success of the U.S. expeditionary force during the 1846-48 Mexican-American War produced a widespread impression among white Americans that their Latin neighbors were weak and incapable of self-rule. Given the prominence of racialized ideologies, these impressions were refracted into essentialist characters of the sturdy Anglo-American pioneer triumphing over the decadent Spanish culture and debased mixed cultures.

Many Americans concluded that further expansion southward was necessary and desirable. A beneficent version of expansionist thought called upon Anglo-Americans to extend their institutions to improve their neighbors’ lot—by force if necessary. The less beneficent version dispensed with the fiction of a civilizing mission. It depicted neighboring countries as bountiful and defenseless, ready to be savaged. Either version attracted adventurers, including soldiers demobilized after the war with Mexico, idealists eager to create new governments, and gamblers who glimpsed immense rewards.

Between 1849 and 1860, there were at least a dozen significant filibustering expeditions, with several more organized seriously but foiled or called off and many more contemplated. May estimated at least 5,000 Americans joined those expeditions, with many more passive supporters and a much larger group fili-curious. Leaders and supporters predominantly came from the Southern slave states, although merchants in the North, especially in New York City, provided crucial support.

The most serious filibuster attempts were those carried out against Cuba and Nicaragua. The Cuban expeditions were led by Narciso López, a Venezuelan-born Spanish colonial official. López turned adventurer in the 1840s when he lost his patrons in the Spanish colonial administration of Cuba. Seeking fortune and fame, he made several attempts to overthrow the government of Cuba, frequently in collaboration with American pro-slavery interests.

A cigar card from the history of Cuba shows the landing of Narciso López in Cardenas on May 19, 1850, as his men raise the flag of the lone star for the first time in Cuba.

A cigar card from the history of Cuba shows the landing of Narciso López in Cardenas, Cuba, on May 19, 1850, as his men raise the flag of the lone star for the first time in Cuba.The Print Collector/Print Collector/Getty Images

American slave owners backed such expeditions because they saw them as a path to enhance their power. As historian Matthew Karp records in his book This Vast Southern Empire, slave owners in the United States viewed the defense of slavery as an international cause. Seizing Cuba would have a double benefit. It would preserve slavery in the Western Hemisphere, fighting against Spanish weakness (and British abolitionist pressures), while bringing a new slave state into the Union. Slavery would be strengthened at home and abroad.

López organized three filibustering expeditions. One was thwarted by American officials for violating U.S. neutrality law. Two landed on Cuban soil with hundreds of armed men each, but both were defeated by Spanish forces, finally leading to López’s public execution by garroting in Havana in September 1851.

López’s brutal end did not deter subsequent aspiring conquerors. In 1853, Tennessee-born William Walker organized a group of 45 followers in an attempt to conquer the Mexican states of Baja California and Sonora and turn them into the Republic of Lower California. Defeated by Mexican forces, he tried and failed again in 1854.

Walker’s Mexican foray complicated official U.S. efforts to purchase parts of Mexico (what became known as the Gadsden Purchase). Yet it also generated notoriety. The publicity he attracted led the opposition Nicaraguan party, the Liberals, to invite Walker to bring several hundred filibusters (officially, to evade neutrality laws, “colonists”) to Nicaragua to bolster their ranks against the rival Conservative party. Although only several dozen men joined Walker, it was enough; he participated in the Liberals’ defeat of the Conservatives and then became head of the Nicaraguan army.

Cunning and ruthless, Walker monopolized power, executing his rivals, setting up a puppet regime, and eventually having himself elected president in sham elections in June 1856. The United States even briefly recognized the Walker regime, although it later rescinded that recognition.

Yet Walker’s regime faced opposition, with now-unified domestic opponents joined by international opposition from Costa Rica and other neighboring countries and figures in the United States (including shipping oligarch Cornelius Vanderbilt, who financed an anti-Walker military force in retaliation for Walker’s nationalizing of his steamboat company). Walker was ousted in 1857 and, after a tour in the United States to raise men and material, made another attempt in 1860, during which he was captured and executed by a Honduran firing squad.


Descriptions of filibustering frequently play up its exotic elements and amateurism. These reinforce the impression that these armed invasions of other countries were aberrations.

But they weren’t that aberrant. Armies, even small ones, cannot be organized spontaneously. Raising an invasion force requires money, logistics, and organization on a substantial scale, and that implies close links to established members of society with the requisite resources. Major parts of the U.S. establishment, especially in the South, winked at the filibusters—and profited from them.

Despite a traditional interpretation stressing the relative strength of the United States and the weakness of neighboring countries, filibustering sprang from the interplay of the weakness of U.S. institutions and the capacity of private American interests to generate almost enough wealth and military potential to seize other countries. Entrepreneurs of coercion exploited the gap between the U.S. government’s inability to foreclose private violence and its unwillingness to provide the conquest that influential interest groups demanded.

The financial side of filibusters resembles financing a corporate hostile takeover. Filibusters offered bonds (at substantial discounts) to be repaid by the government they would establish. Enough sophisticated investors were willing to speculate that the politics of expansion would eventually guarantee them a payoff that filibustering expeditions could repeatedly raise funds through this method. That, in turn, tells us these expeditions were not aberrations. Capital and political influence, then as now, ran in closely linked networks, and the participation of officials such as Mississippi Governor John Quitman (who recruited for López’s 1850 expedition) reinforced savvy investors’ belief that a successful filibustering expedition might pay off if the United States recognized a new regime.

Filibusterers and their backers miscalculated on two fronts. First, seized by notions of racial and cultural superiority, they chronically underestimated the societies they sought to conquer on the cheap—even as they repeatedly failed. Second, they misgauged the likelihood they would receive U.S. support once the takeovers happened. Southern capital might have backed them, but political power in Washington didn’t. Far from good wishes or tacit collaboration, filibusters much more consistently faced opposition from presidents and federal officials. As May stresses in his book on the history of filibustering, the recognition of Walker’s government only took place once an apparently fully Nicaraguan government, represented in Washington by a Nicaraguan native, had supposedly consolidated control—and was revoked after Walker seized the presidency for himself.

To be sure, punitive federal action could face local opposition (which made jury convictions on charges like violating neutrality acts hard to secure). Furthermore, the 19th-century U.S. government was comparatively weak, allowing some expeditions to proceed. Yet even given these obstacles the government repeatedly stopped expeditions before they could even set sail.

These conditions explain why filibusters were more an expression of weakness than strength. Relying on private sources was a second-best strategy. Slave owners and others who supported filibustering expeditions would have vastly preferred to have the public pick up the tab than to have to pay for them personally. Yet, besides the Gadsden Purchase and the annexation of uninhabited guano islands, expansionists of the 1850s could not secure official backing for their plans as earlier expansionists had during the 1840s.


Filibusters failed but their legacy lingers. Powerful European countries, including the United Kingdom, saw filibustering confirming portraits of the rising United States, perhaps not inaccurately, as a violent, unstable country with either a feeble or duplicitous government.

More directly, filibustering contributed to Central America’s continuing institutional turmoil. May argues that the Nicaraguan Liberals’ alliance with Walker helped discredit liberal movements throughout Central America. Filibusters also helped identify nationalism with anti-Americanism. The memory of filibusters in Mexico, Cuba, and Nicaragua is much stronger than in the country from which they came. Filibusters’ victims understandably counted the experience of being invaded by violent marauders as a stronger signal of American intentions than what appeared to be only rhetorical official efforts at stopping the expeditions.

It is not hard to draw connections between the long-term deficit of stable institutions in Central America and violent U.S. interventions there. Even if the filibusters themselves were not officially sanctioned, they were also not officially quashed, and they form part of a continuum of interventions in Latin America and beyond, from United Fruit to Iran-Contra, that mixed private and official interests.

Filibustering expeditions may be relegated to the margins of Americans’ historical consciousness, something all the more surprising given their imprint on U.S. discourse. As political scientist Gregory Koger writes, legislative delays were a part of American politics from the beginning. What they lacked, however, was a snappy title. “Filibustering” so well captured the piratical spirit of such tactics the use of the term in reference to legislative behavior emerged even before Walker’s Nicaraguan expedition.

In a reflection of divided U.S. opinion about filibustering expeditions, there were whiffs of both obloquy and romantic extremism in the term. One “dictionary of Americanisms” defined filibustering as “the sharp maneuvering of one political party to get an advantage over an opponent.” This makes sense: Filibustering expeditions aimed to present the U.S. government with the fait accompli of a conquered country, forcing action by violently short-circuiting democratic responsiveness. Legislative filibustering is a power play that short circuits the majority’s ability to control the flow of legislation. For representatives of powerful minority groups, in both cases, extremism in pursuit of interest is no vice.

The conceptual links between the 1850s filibusters and their legislative namesakes are, then, somewhat stronger than they may appear at first glance. As legislative expert Sarah Binder makes clear, the legislative filibuster was never an expression of deeply held principles favoring unlimited debate to further deliberation. And although legislative filibusters are not limited to anti-civil rights agendas, it nevertheless is arresting to consider the analogous interests between prominent supporters of violent, pirating filibusters then and of legislative filibusters now.

The cost of both types of filibusters must be measured in more than the direct damage they caused but in the loss of confidence in the U.S. government and the consequences such a loss has for policy domestically and abroad. That the legislative filibuster could be ended by a simple vote—far easier than stopping filibuster expeditions—makes its endurance all the more remarkable.

Paul Musgrave is an assistant professor of political science at the University of Massachusetts Amherst.

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