The qualms about the Caribbean (and about New Orleans) fed qualms about the illegality of filibustering. Before U.S. filibusterers could replace foreign regimes, they had to defy their own national’s Neutrality Laws. Back when the new American government had striven to be neutral in Europe’s Napoleonic Wars, Congress had passed these laws. These edicts required private individuals to be as neutral as their government. American citizens could not join foreign wars, civil conflicts, or revolutions when the United States remained at peace with the combatants. . Federal officials could seize suspected filibusters before they sailed from America. If convicted, suspects could be fined up to $3000 and jailed for up to three years.

In the presecession years, the northern presidents who presided over national laws enforced these edicts enthusiastically. Both Pierce and Buchanan sought legal purchases in the Caribbean as zealously as they repressed illegal freebooting from the United States. That even-handed attitude toward expansionism, they believed, best ensured sectional peace. Intolerance for lawbreakers also best preserved a nation worth saving.

On the evening of October 16, 1859, the liberator led fourteen other whites and four blacks from his rented Kennedy Farm in Maryland to Harpers Ferry, those six miles distant. There the Potomac and Shenandoah rivers unite to heave against a jagged semimountain, before flowing on to the sea….There transpired one of the most stupendous scenes in American history. In the dark night, Brown's freedom fighters easily captured Harpers Ferry's federal armory, arsenal, and engine house…No other first strike has ever been better planned or carried out (which is only to say that John Brown here perfected his lifelong specialty). No other following tactics have ever been botched so badly (which is only to say that John Brown here succumbed to his lifelong flaw). Where these raiders meant to kill whites, in order to free blacks, they first killed a free black, Shepard Hayward, as he walked harmlessly away from them.

"John Brown, the same warrior who would assault Harpers Ferry, Virginia, in 1859, massed six followers, including four of his sons, against slumbering proslavery settlers on the Pottawatomie Creek, some thirty miles south of Lawrence. Brown and his henchman dragged some five men from rude log cabins. They shot their victims, slit them open, and mutilated their corpses. With Brown’s celebration of an eye for an eye, the nation’s problem was not just that proslavery violence spawned antislavery violence. The worse problem was that more Kansas and more Northerners than John Brown, whatever they thought of black slavery, already preferred civil war to slaveholder repressions of white men’s republicanism. Thanks to the aftermath of the Kansas-Nebraska Act that Davy Atchison’s followers had spawned, a continuing Kansas crisis loomed huge on the national horizon."

Like all the extremists who ultimately made a revolution, [John] Quitman considered southern moderation the barrier to destiny. He saw southern national party politicians as keepers of slaveholders’ prison. In their hunger for national party patronage, politicos dumbed down awareness of the South’s dangerous problems and taught the folk to cherish compromised solutions. Like [William L.] Yancey and all the other ultras, whether they operated inside or outside a national party, Quitman meant to find the issue that would remove the blinders from falsely educated eyes. 

Yet what made this charismatic educator so unforgettable was less his success at teaching Southerners to be ultras than his capacity to stay simultaneously northern – to remain a very shrewd and practical operator – even in his highest southern flights. No other southern extremist charged ahead so recklessly – or reconsidered so cautiously. Before his Cuban adventure, this Mississippi governor advocated disunion, in response to the Compromise of 1850. In his typical buccaneering spirit, the governor told South Carolina secessionists to back off for a moment. Then he would lead Mississippi out of the Union first. Skittish South Carolinians gladly obliged. But Quitman, after reconsidering, saw that his pledge had come too soon. So momentum was lost, secession folded, and the chagrined fire-eater learned never to move again until he had the firepower to triumph.  By accepting that lesson, Quitman showed he was no [William] Walker, no [Narciso] López, just a shrewd ex-Yankee who sought to make practicality a  hallmark of the southern extremist.