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On the eve of the Civil War, the U.S. Army’s commanding general, Winfield Scott, was just about used up. Few players on the American scene could stand the old goat when he was in his prime, and now that his advancing age and flab had rendered him a non-factor in active duty, no one was inclined to listen to his incessant harping about—well, you name it.

Too prickly to love, too talented to ignore, he had been tolerated as a necessary irritant since Thomas Jefferson’s presidency. Brilliant on the field, obsessed with minutiae off, Scott, now 74, was a man of lavish tastes, a volcanic temper and enough complexes to satisfy the most demanding therapist.

The public appreciated him, but not enough to elect him president. Cartoonists gently lampooned him, but respected him too much to savage him as they did with practically every other character of such color.

Scott loved ceremony and extravagance, but his modest finances couldn’t keep pace. Several times he was implicated in a monetary scandal, and he once argued that he was due a pay raise based, somehow, on a liberal interpretation of the lunar cycle.

For the cameras, Scott could still be counted on to drape his massive frame in yards of ornamented upholstery and stare haughtily at the lens. There was hardly a better nickname than the one bestowed on him: “Old Fuss and Feathers.” But, oh, what a soldier, what a strategist he had been. Like many men of genius, the general’s ill temper and boorish behavior were accepted in the bargain because he produced results. Now, as the nation entered its darkest hour, Scott was the logical savior-in-residence Abraham Lincoln could turn to for a plan that would snuff the spark of the upstart Confederacy before it had a chance to flame.

And indeed, Scott did have a plan. It involved one massive military campaign in the West, where the South was not expecting it, and one massive military campaign at sea, which the South had no means to combat. After that there was nothing to do but sit back and wait for the Confederacy to implode. Cut off from the world economy, this new Southern government would wither and die.

To detractors, it sounded a lot like the South American water snake that slowly—key word “slowly”—suffocated its prey. They gleefully christened Scott’s plan “Anaconda.”

Scott outlined the strategy in a May 3, 1861, letter to General George B. McClellan. A “strict blockade” of the seaboard, he wrote, was required in the East and in the Gulf of Mexico. Out West, a vanguard of 12 to 20 gunboats would steam down the Mississippi River, followed by 40 transport ships carrying 60,000 soldiers. The soldiers would need to hop off their boats on occasion and turn Confederate batteries along the river, and these posts, in Union hands, would guard against supplies entering the South from points north and west. Finally, New Orleans was to be occupied and strongly held “until the present difficulties are composed.” Central to Scott’s thinking was that his plan would require “less bloodshed” than any other strategy under consideration.

The only flaw rested not in anything the South could muster, but with growing Northern impatience. Scott saw the issue: “The greatest obstacle in the way of this plan—the great danger now pressing upon us—[is] the impatience of our patriotic and loyal Union friends,” he wrote McClellan. “They will urge instant and vigorous action, regardless, I fear, of the consequences.”

Ever the detail-oriented military professional, Scott wanted time to raise and train the troops, time for the rivers to rise to better accommodate his boats and time for the frosts to whiten Memphis, Tenn., lessening the risk of yellow fever.

But in the wake of the South’s opening salvo at Fort Sumter, Northerners were no longer interested in sanctions or never-ending preparations. They wanted to do the one thing Scott’s plan did not envision: Kick some tail.

By this time, Scott’s health was poor and his political capital had long since withered away. Nobody had heeded his advice to strengthen the South Carolina forts before the Rebels could occupy by force, and now the consequences were evident. So he submitted his reptilian plan with little hope of its success. “Bah,” Scott reportedly snorted, with a wave of his hand. “No one ever listens to me anyway.”

The primary objection to the plan was its lack of speed, but another was more nuanced. Some of the young bucks who had last seen action in the Mexican War were itching for their chance at heroics, and few medals are given for sitting idly on the deck of a ship taking potshots at smugglers. Indeed, the only real mili­tary action called for in the Anaconda Plan was in the West. Aside from that, there was little to do but move chess pieces around the board.

Most of these pieces had sails and wooden hulls, much to the dissatisfaction of Navy Secretary Gideon Welles. To blockade the South required a network of ships capable of sealing 3,500 miles of coastline from Virginia to Mexico. At the start of the war, Welles had the services of about 80 leaky old boats. This was the effective equivalent of guarding the distance between Washington and Richmond with about two batteries of artillery. To Welles, the logistical problems were obvious.

But to Scott, the logistical problems for the South were obvious as well. Both of Anaconda’s main thrusts involved water, an element in which the South had no viable response. At that point, the Confederacy could scarcely scrape together a dozen seaworthy ships. Things got a little better for the Southern Navy, but it could never boast much more than 100 ships, a sixth of the Union total by war’s end. Indeed, much of the South’s naval strategy involved tossing a lot of explosive flotsam in its harbors to dissuade Union naval attack, and chasing down Northern whaling ships on the high seas with a handful of elite clippers.

Yet for the North, with the naval advantage came a diplomatic disadvantage. This was not a war between nations, but a rebel insurrection. To blockade Southern ports was a virtual admission that the Confederacy was indeed independent (a nation would have no need to block its own coastline) and the Anaconda Plan might inadvertently invite European nations to recognize the Confederate States of America.

Worse was the implication for European economics. Britain in particular was tightly woven to the Southern cotton trade, while Britain and France both licked their chops over the prospects in a potentially lucrative arms trade with the Confederacy.

But Lincoln declared an initial blockade of Southern ports on April 19, 1861, less than a week after the fall of Fort Sumter, and the Union began building ships. In the nine months that followed implementation of the Anaconda Plan, Welles’ Navy added 182 ships to its fleet. By the end of the war, the Union had more than 600 modern vessels. But even with its burgeoning fleet, the North could never hope to stop many of the blockade-runners, although it didn’t really have to. Early in the war, five of every six attempts to breach the Yankee water web were successful, but the boats used by the blockade-runners were by necessity small and fast, capable of carrying only a fraction of the cargo that a standard freighter could. The South could run some guns and dry goods, but it could never move its most precious commodity: bulky and heavy bales of cotton.

The job of securing the North Carolina coast fell to Ambrose Burnside, whose fortunes peaked early in the war. Later maligned for his efforts at Antietam and Fredericks­burg, Burnside’s performance at the Outer Banks was to pay incalculable dividends for the remainder of the conflict.

In September 1861, Burnside received command of the North Carolina Expeditionary Force and, after a fitful and soggy sail down the Chesapeake Bay, launched a successful assault on the Outer Banks. In little more than six months, Confederate shipping was shut down along more than three-quarters of the North Carolina coastline.

Benjamin Butler’s capture of Forts Hatteras and Clark in August 1861 opened the door to Burnside’s eventual success in the North Carolina Expedition. Butler continued on to operations in the Gulf of Mexico, and captured Ship Island in December 1861. The following May he led his men into New Orleans, after the Union Navy had made short work of Forts Jackson and St. Philip. Many in the populace mocked the invasion and Butler’s controversial term as the city’s military governor by etching Butler’s likeness in the bottom of their chamber pots.

Many historians have credited the capture of New Orleans on April 29, 1862, as being the war’s de facto turning point—not for military reasons, but for its economic ramifications, just as Scott had predicted. For all the South’s celebration of states’ rights, that ideal had one obvious and crippling effect: The Confederacy had no central control of banking and taxation. The North passed a national income tax on July 1, 1862, and a year later approved the National Banking Act, which provided a vehicle for efficiently raising cash.

Pretty much all the South had was cotton, but it was a weighty ally. It was because of cotton that the South assumed it could bend Europe to its will, and for a time it appeared this arrogance was justified. The South issued bonds backed by the cotton crop maturing in its fields; the bonds paid 7 percent, but no one had his eyes on the coupon. The appeal was that the bonds could be redeemed for cotton at cheap, pre-war prices. For the South, these bonds simultaneously became a spectacular success and a spectacular failure. As the price of cotton sharply rose during the war, these bonds became more and more valuable. But for the South, the rising value of cotton had ceased to be a good thing.

Prices skyrocketed specifically because of Butler’s occupation of New Orleans, and because the South had no way to get its new crop past the blockade to the European markets. “The Confederacy had overplayed its hand,” Niall Ferguson wrote in The Ascent of Money. “They had turned off the cotton tap, but then lost the ability to turn it back on.”

The economic heart of the Confederacy, the mouth of the Mississippi, now had a stake through it—from 1862, the value of goods crossing New Orleans docks plummeted from $500 million to $50 million. Because of the blockade, 95 percent of the Southern cotton trade was stifled and some plantation owners were forced to put the torch to mountains of cotton bales when the smoke on the horizon indicated the coming of Union gunboats.

The blockade elicited a fabulous game of cat and mouse, as the North’s tightening grip led to ever-greater acts of Southern audacity. Merchant ships from England would sail to staging areas in the neutral Caribbean nations before making the last run to Southern soil—at least until the North began snagging ships on their way to the islands. So some English merchants, in need of another staging area, settled on, of all places, the port of New York City. It was a creative, if short-lived, solution. By the end of the war, most every nautical dodge imaginable had been tried by the South and countered by the North. Initially sneered at, and admittedly impotent at the outset, this key component of Scott’s Great Snake became ruthlessly effective as the war progressed.

After the occupation of New Orleans, it took the Federals another year to gain complete control of the Mississippi River by capturing Vicksburg. “The father of waters,” Lincoln remarked after the city surrendered, “again goes unvexed to the sea.” Union boats were unvexed as well, and after Vicksburg unarmed Union ships could float unmolested from St. Louis to New Orleans. It was as the Anaconda had foreseen, if perhaps a little late in coming.

For the South, the loss of the Mississippi meant the loss
of military supply lines, communication, rail lines and trade. In other words, its Western markets were going the way
of its European markets. And while the loss of European
markets meant the loss of financial capital, the loss of the Western mar­kets meant the loss of something even more essential—food.

Few plantation owners had been terribly interested in growing wheat, given the potential fortune to be made from raising cotton. So when war came, Southern agriculture was not equipped to feed its own, especially after Western mar­kets became un­reachable. Without trading partners or contemporary financial instruments, the South began churning out money that almost literally wasn’t worth the paper it was printed on. Prices soared, and by spring 1863 bread riots were spreading across the South. On April 2, 1863, 60 people were arrested in Richmond after a mob of women marched on the governor’s mansion chanting “Bread or Blood.” The mayor actually read the protesters the riot act, to no avail. (See “Her War,” p. 20)

The squeeze of the snake was beginning to tell. Confederate officials, not wanting this news to reach the North, urged all involved to keep their mouths shut, lest the Yankees understand the desperation creeping through the South. In one short year, everything had changed.

On July 4, 1862, the Richmond Dispatch penned an editorial mocking the U.S. Congress for remaining in session under the assumption that the fall of the Confederacy was imminent, and there might be a surrender to adjudicate. Overconfidence was, the paper noted, becoming a July 4 tradition: “On the last Fourth of July there was to have been, according to the orders of that magnificent ass, Abraham Lincoln, and a flaming programme in the New York Herald, a general, combined, simultaneous march of the universal Yankee columns, East and West, upon the strongholds of the Southern Rebellion, which were to be chewed up and exterminated without farther delay.”
But the bravado masked a reality Anaconda was primed to expose: Slavery had made a mess of the Southern economy. Market forces had been mutated by an excess of un­paid labor, creating economic and social poltergeists too many to name.

Traveling in the South just before the Civil War, Frederick Law Olmsted—the man who built Central Park with help from, of all people, Dan Sickles, the scourge of Gettysburg—found unspeakable poverty, cemented in place by an unwillingness of poor whites to perform the manual labor associated with slaves. “They [poor, white Southerners] work little, and that little, badly; they earn little, they sell little, they buy little and they have little—very little—of the common comforts and consolations of civilized life.” They had one thing going for them, freedom, that slaves did not, and they parlayed this into an air of superiority and a reason to eschew manual labor and industry. In many areas, in fact, Olmsted discovered dirt farmers plowing their weedy fields with pointed sticks, a technology the Chinese had surpassed two millennia before.

An inordinate majority of the South’s wealth came from cotton, and much of the profit was spent on slaves. So inefficient was this structure that labor became too valuable to be frittered away raising other crops—food, for instance. “It is frequently spoken of as a mystery that the cotton planters cannot be induced to raise the food required for their [slaves,]” Olmsted wrote. “The reason of it is a very simple one; namely that in the cultivation of corn their labor must come into competition with the free labor of the Northern states.”

Slavery was economically viable in the production of cot­ton only because the North couldn’t grow it. And plantation owners were as enslaved to cotton as their laborers were to them. Most all the South’s capital was tied up in the crop, and the only industry that rivaled cotton was the production of the labor needed to grow and ship it. No other industry mattered, and few seemed industrious enough to branch out into something new. In short, after cotton was removed from the
equation by the Anaconda Plan, the Southern economy was in danger of complete collapse, with or without a war.

By 1862 the war was going better for the North than modern conventional wisdom might consider. At least it was in the theaters of operations foreseen by Winfield Scott. Only in the full frontal assaults Scott had so presciently warned against had the North become a punching bag. On the Mississippi and the Southeastern seacoast, the snake was performing quite well.

Scott, by this time, was not. Although he would live to see the Union victory (a victory thanks in no small part to Anaconda), by November 1861 he had been forced into retirement, largely attributable to the sniping of his one-time protégé George McClellan, who couldn’t decide whether Scott’s passive plan made the old man “a traitor” or merely “incompetent.” So McClellan did what Scott was afraid to, and set out for Richmond. On June 24, 1862, Lincoln—unconvinced of McClellan’s abilities—paid Scott one more visit up in West Point, N.Y. Scott urged Lincoln to send Irwin McDowell to help out McClellan on the Peninsula. Lincoln didn’t and McClellan, certain he was outmanned, got cold feet and backed away from Richmond at a time when, but for a few more men, victory might have been at hand.

Soon McClellan was back in the nation’s capital, a haversack full of excuses and assigning blame to one and all. Scott would have been permitted a smirk. In a letter to Lincoln a month before his Anaconda entreaty to McClellan, Scott had outlined all the potential disasters that might accompany a traditional army assault—adding, “cui bono?” For what?

As Scott’s Great Snake began effectively squeezing pressure points in the Confederacy, McClellan became the military embodiment of the unpleasant results Scott had warned Lincoln about the previous year: “The loss of hundreds of thousands of men to skirmishes, sieges, battles and Southern fevers; a frightful destruction of life and property in the South; a reconstruction that would cost four times what the nation would take in from Southern tax revenues; and generations of bad will from a conquered but unrepentant people.”

For what, indeed?

Tim Rowland is a regular contributor to America’s Civil War and the author of Strange and Obscure Stories of the Civil War (Skyhorse Publishing, 2011).