Winfield Scott was one of America’s greatest generals—a war hero many times over and a man whose struggle to professionalize the United States Army shaped much of the nation’s early history. His achievements were considerable and his tenure long: he served 14 presidents. But he had the misfortune to serve in two conflicts—the War of 1812 and the controversial Mexican-American War—bracketed by the far more significant American Revolution and Civil War. Since his death, Scott has faded into the background of American history.

Even more obscure is Scott’s long association with New York City, where he lived and worked for much of his adult life. Though born in Virginia, Scott died an urbanite, marked indelibly by Gotham. He was an immediately recognizable figure on Manhattan’s streets, at home in the salons and dining rooms of Knickerbocker New York’s finest society and referred to frequently in the diaries and memoirs of the era’s prominent citizens. Leading New York Whigs supported Scott’s presidential bid. He even directed the United States Army from the city. His time in New York influenced one of the most significant decisions of his life: to remain with the army instead of joining the Confederacy at the outbreak of the Civil War. His native Virginians burned him in effigy for that choice, and he remains a controversial figure in the South. New Yorkers, by contrast, simply forgot him.

Scott was born in June 1786 at his family’s farm near Dinwiddie Courthouse, southwest of Petersburg, Virginia. His grandfather was a Scotsman who had supported Bonnie Prince Charlie in his doomed effort to win the English crown. After the prince’s defeat at the Battle of Culloden in 1746, Scott’s grandfather fled to America, “smuggled on board a ship bound for Virginia,” as Scott wrote in his memoirs. There, he prospered as a lawyer and bore a son, William, who served as an officer in the Revolutionary War and became a prominent Petersburg citizen. William married Ann Mason, the daughter of a prosperous local family, and the pair left their son, Winfield, the means to enjoy the life of a well-to-do Virginia landowner.

But Winfield Scott was eager for adventure. When British sailors aggressively boarded an American ship in 1807, hunting deserters, Virginia’s governor called for volunteers to join the state militia and counter the threat. Scott raced to enlist. Given command of a squad stationed near Lynnhaven Bay, he nearly set off an international incident when he and his men captured eight British sailors trying to steal ashore. President Thomas Jefferson, fearing an escalation, ordered him to free the men. Still, Scott recalled in his memoirs, Lynnhaven Bay was where he first heard the “bugle and drum” of military service. “It was the music that awoke ambition,” he observed. Through friends, he gained a commission in the regular army from Jefferson; ordered himself an elaborate, custom-tailored officer’s uniform; and was posted to New Orleans. The young soldier discovered an early American army governed by officers “sunk into either sloth, ignorance or habits of intemperate drinking.” After bad-mouthing his superiors, he was court-martialed and suspended from the army for a year.

Only the prospect of war with Britain saved his career. Reinstated in late 1811, Scott was sent north to the border between New York and Canada, where his uniform and six-foot-five-inch frame led one observer to describe him as the “beau ideal of a gallant soldier.” Scott received orders to assist local militia in an assault on positions across the Niagara River from Buffalo. Crossing the Niagara, he boldly took command of the small American force, which had captured Queenstown Heights and was preparing for a British counterattack. With Scott racing up and down the lines, the force repulsed several waves of British regulars, Canadian militia, and Mohawk braves. But Scott’s requests for reinforcements went unheeded. “Not a regiment, not a company is willing to join you. Save yourself by retreat,” the commanding general of the militia wrote Scott. He undertook instead to defend the Heights. Eventually, the British drove most of his men off their positions and captured the rest, including Scott.

The battle of Queenstown Heights may have been a strike against an early American military system that relied heavily on local militia, but it was a triumph for the young commander. After the British released Scott, President James Madison promoted him to colonel and sent him back to the conflict-ridden border. In the summer of 1814, Scott, commanding a brigade, entered Canada and led his soldiers into battle at Lundy’s Lane, near Niagara Falls. Cornered by a much larger British force, Scott engaged in a vicious two-day battle. The two sides lost more than 850 men. Wounded several times, Scott was ultimately carried to safety before both sides left the field, exhausted by the long battle.

For the first time in the War of 1812, United States regulars had proved that they could match the best fighting soldiers in Europe. Scott’s injuries ended his role in direct combat in the war, but he won a promotion to major general, and Congress ordered a gold medal struck in his name. Many years later, that medal was one of the few items left untouched when thieves cleaned out the vault of City Bank of New York, where Scott had stored it. One robber, later captured, said that he “was not such a villain as to rob a gallant soldier.”

Miner Kilbourne Kellogg's 1858 portrait of Scott, which hangs in City Hall

After the war, a group of congressmen lobbied to get Scott appointed secretary of war. Just 29, Scott wisely turned them down, but he accepted a commission to travel to Europe and study professional soldiering there. Then, in May 1816, Madison gave Scott command of the country’s Northern Military District, headquartered in New York City.

It proved a historic posting. Hard as it is to imagine today, New York was a major military outpost, essential to the young nation’s defense. Just before the War of 1812, city and state officials, remembering the British occupation of New York during the Revolution, had embarked on a building program to strengthen the city’s defenses. They enlarged batteries in lower Manhattan into a fort (later called Castle Clinton), built more forts and gun emplacements on the beaches of Staten Island, added garrisons along the East River to repel invasion via Brooklyn, and heavily fortified the Harlem Heights along the East River. By the end of the war, nearly 600 artillery pieces guarded the city, and four arsenals were in place around town, including a huge federal depot in what’s now Madison Square. About 25,000 men were in uniform in a city of just 100,000 inhabitants. New York was perhaps the most heavily armed city in the country.

The city hadn’t lost its martial atmosphere by the time Scott assumed command. Thousands of New Yorkers were militia veterans, and many top political leaders had served as officers. The city ardently celebrated patriotic holidays like Independence Day with parades and cannon salutes. It even observed an anniversary, long since forgotten, known as Evacuation Day, which commemorated, every November 25, the British withdrawal from the city at the end of the Revolutionary War. This military New York welcomed the young war hero. On Scott’s first Evacuation Day celebration, in 1816, New York honored him for his bravery along the Canadian border. Governor Daniel Tompkins presented him with a sword struck in his honor “by the people of this state, as a pledge of their affection and gratitude for your distinguished services.”

One of only five generals in the nation’s regular army—and the youngest—Scott was determined to make a spectacular career. Soon after coming to New York, he secured Congress’s permission to develop a code of conduct, regulations, and organization for the army, based on his study of European techniques. His work, General Regulations for the United States Army, appeared in 1821 and anticipated the much larger army that would emerge in the Civil War and after. It earned Scott the nickname “Old Fuss and Feathers” for his insistence on discipline and proper procedure. Scott also saw the significance of nearby West Point, which President Jefferson, fearing the establishment of a permanent American officer class, had created only reluctantly in 1802. Scott worked to improve training at the school and frequently made the journey north from Manhattan to lecture and to tutor students there.

Scott swiftly took his place within flourishing postwar New York. After the British lifted their blockade at the end of the war in 1815, European goods had begun flooding into New York Harbor, boosting the city’s economy. Then, in 1825, the Erie Canal opened, unleashing new waves of commerce and wealth. Construction pushed New York City’s limits up Broadway past today’s Canal Street. A swamp to the west of Canal Street known as Lespinard Meadows was drained and transformed into an elegant residential and commercial district, where Scott briefly kept his army offices. Further north, building commenced in the mid-1820s around what became Washington Square. In 1824 alone, records show, more than 1,600 brick houses rose in the city. The next year, the city’s population climbed to about 166,000, up from 100,000 during the war.

Not long after arriving in New York, Scott wooed and won a wealthy Southern beauty, Maria Mayo. Her family boasted an estate in Elizabethtown, New Jersey, at the mouth of the Raritan River, which they gave to Scott and his bride. The young couple became a glamorous addition to the city’s social scene. Scott often appeared at prominent Knickerbocker social functions in full dress uniform; any given night could find him, say, at a dinner at the City Hotel on lower Broadway honoring Washington Irving, or dining with Daniel Webster at the Union Club. Among Scott’s friends and confidants was Philip Hone, a successful auctioneer who served as mayor in 1826 and 1827 and left us a detailed portrait of Old New York in a two-volume diary sprinkled with references to the general. Some of Scott’s favorite haunts opened during this period, including Astor House—the city’s first luxury hotel, where he sometimes stayed when it was too late to make the two-hour trip back to Elizabethtown—and the famous restaurant Delmonico’s.

Unlike many generals of his era, who projected the image of rough-and-ready frontiersmen, Scott saw himself as a gentleman with cultivated and urbane interests. For example, Erasmus Keyes, his aide, wrote that the general considered “knowledge of the culinary processes a necessary accomplishment of a gentleman and a soldier.” On a visit to France, Scott learned the proper art of baking bread. Returning to New York, Keyes reported, the general informed William Cozzens, the proprietor of the American Hotel on lower Broadway, that his bread wasn’t worth serving at a kennel—and barged into the kitchen to show the staff how to do it right.

New York’s salons taught Scott some valuable, if painful, lessons in diplomacy. A voluble, frequently indiscreet man, Scott nearly ruined his career at a dinner party shortly after arriving in the city. In April 1817, Andrew Jackson, whose victory at New Orleans in the War of 1812 had eclipsed Scott’s own exploits, sparked a controversy by countermanding an order from Washington. Jackson, the epitome of the American hero as frontiersman, showed little patience for directives from central command—directives that Scott was helping fashion. At the dinner, as Scott and New York governor-elect DeWitt Clinton animatedly discussed the incident, the general suggested that Jackson’s actions amounted to mutiny. One of those present wrote an anonymous letter about the exchange, which the Columbian newspaper published. An enraged Jackson challenged Scott to a duel, which he turned down. But Jackson’s enmity would threaten Scott’s career, especially after Jackson was elected president 11 years later. Only Scott’s valuable experience and talents as a soldier, which Jackson recognized and needed, saved him.

Scott’s military feats were indeed prodigious. During the more than 30 years between the War of 1812 and the Mexican-American War, he left New York to undertake a series of difficult military tasks, including presiding as commander during the Black Hawk Wars in the Illinois Territories and defusing a confrontation between secessionists in South Carolina and the federal government in the 1830s.

These exploits made Scott a force in local and national politics. He was instrumental in founding the New York wing of the Whig party, which coalesced around opposition to Jackson’s political agenda and included such prominent figures as Horace Greeley (founder and editor of the country’s most influential newspaper of the time, the New York Tribune) and William Seward, who served as New York’s governor and later as Abraham Lincoln’s secretary of state. Scott might have become a willing Whig simply because of his old enmity toward Jackson. But he also fiercely opposed Jackson’s destruction of the Second Bank of the United States, the nation’s central bank during the early nineteenth century, whose charter the president refused to renew in 1832. Scott believed that a central bank was essential to the country’s well-being, since it could help regulate government credit and ensure a stable currency. He also feared that Jackson’s ideal of the military man as frontiersman threatened West Point and might ultimately defeat his own ongoing efforts to give the country a professional officer corps.

In 1839, Scott received his first serious consideration for the presidency, emerging as a dark-horse candidate for the Whig nomination at the party’s December convention in Harrisburg. He had just returned from a successful effort to settle a border dispute between Maine and Canada that had almost brought a sequel to the War of 1812, and his stock was high, especially in the Northeast. Henry Clay and William Henry Harrison were the two leading Whig candidates, but New York Whigs floated Scott’s name as a compromise in case of a convention deadlock. Scott remained in the running for several ballots, though the convention eventually nominated Harrison.

Two years later, the army’s commanding general, Alexander Macomb, died. Scott, the nation’s best-known soldier after Jackson took to politics, was the natural choice to replace him.

Scott’s demanding new job didn’t remove him from the battlefield. Tensions began to mount between Mexico and the United States over the disputed border of Texas, and Congress declared war on May 13, 1846. United States forces, led by Zachary Taylor, achieved several significant victories in Texas. Yet to win the war, President James Polk realized, America would have to bring the fight to Mexico itself. So Polk, a Southern Democrat, deployed Scott to launch an unprecedented amphibian invasion. Scott assembled 70 vessels and 12,000 troops on Lobos Island, off the Mexican coast, and landed them in specially designed surfboats. The troops then laid siege to the heavily fortified coastal city of Veracruz. After three weeks, the fortress city fell.

The United States and the world greeted Scott’s landing and victory with awe, but the general was just getting started. After securing Veracruz, Scott marched with his army across Mexico, following the route that Cortés had taken more than 300 years earlier. As he moved inland, Scott’s lines of communication with his coastal headquarters were stretched so thin that he decided to cut ties with his base, leaving his army few options if it went down to defeat. In London, hearing of the risky move, the Duke of Wellington declared: “Scott is lost.” But Scott’s army, though reduced by sickness and casualties, scored a series of victories against the Mexican general Santa Anna, eventually capturing the fortress of Chapultepec outside Mexico City and then storming the gates of the capital itself. In the New York Times, Wellington called Scott “the greatest living soldier.” A deputation of Mexican ministers visited Scott in his camp and asked him to serve as Mexico’s dictator until the country’s political situation stabilized. Scott turned them down, perhaps figuring that his political fortunes back home were about to soar.

They didn’t. President Polk, fearing that the general’s popularity might make him a formidable rival in the upcoming presidential election, relieved him of his Mexican command and summoned him to Washington to defend disciplinary actions that he had taken against some politically connected officers during the campaign. While he was engaged with a court of inquiry about the affair, the Whig Party nominated the conflict’s earlier hero, Zachary Taylor, for president. The affair rankled Scott’s supporters. “The Duke of Wellington, with no better claim upon his country’s liberality than our Scott, bends under the weight of merited rewards,” Philip Hone wrote in his diary, “whilst our ripe and accomplished soldier . . . is recalled to be laid upon the shelf.”

New Yorkers tried to assuage some of the indignity that Scott had suffered with a huge celebration in his honor on May 25, 1848. At 11 AM, a steamer left Battery Park with a host of dignitaries to pick Scott up at Elizabethtown. After embarking with the general, the steamer plied its way across New York Harbor, where a battery of 13 guns on Governors Island blasted a salute. The dignitaries then alighted at Castle Garden—the old Castle Clinton, transformed into an auditorium and entertainment complex—where the day’s festivities began. (In 1975, the federal government restored the landmark to its original design as a fort.)

Accompanied by four brigades of New York militia, Scott paraded up Broadway in a route that took him across lower Manhattan and ended at City Hall. Then he proceeded to Astor House for a dinner in his honor. Describing the scene at Astor House, the New York Herald wrote: “An immense crowd filled the street, the place, and every avenue, and the General, to reach the steps of the hotel, passed through a dense lane of living beings, forming one compact solid mass. Loud cheers resounded on all sides.” Scott announced to the crowd that he was “happy to be in the hands of my fellow-citizens of New York, a city . . . in which my lot has been cast for a portion of 30 years of my life.” And he paid tribute to the army that had fought under him in Mexico, observing that “a very large portion of the rank and file of that army, regulars and volunteers, went forth from the City of New York, to conquer or to die.”

By 1850, Scott’s supporters were talking again about a presidential run. But when his turn on the national political stage came in 1852, it was perhaps the worst possible moment for a Whig candidate. The party that had formed in opposition to Jackson fractured after Old Hickory’s death in 1845. Northern Whigs increasingly supported the abolition of slavery, while the party’s Southern elements backed a package of compromise bills in 1850 that banned slavery in some western territories but also strengthened the Fugitive Slave Act, requiring the return of runaway slaves to their owners. At the party’s nominating convention in Baltimore, the Whigs crafted a platform that some Northern Whigs refused to endorse, since it continued to compromise on slavery. After 53 ballots, the party decided on another compromise: when the incumbent president, Millard Fillmore, failed to attract enough votes to win renomination as the Whig standard-bearer in a three-way race with Daniel Webster and Scott, key delegates from Virginia swung toward their native son, giving Scott the nomination.

But the Whigs melted away around him. Some members broke off to join the newly created Free Soil Party, which opposed the expansion of slavery to new American territories. Others, from the South, were unenthusiastic about Scott’s association with the New York wing of the party and sat out the campaign. Scott didn’t help himself, either: unlike his old nemesis Jackson, he lacked the common touch, tending to talk over the heads of average citizens during campaign appearances. And he found himself the subject of bitter personal attacks. Democrats used the fact that Scott’s daughter had converted to Catholicism and joined a convent to alarm the country’s overwhelmingly Protestant electorate by charging that the candidate was a Romish sympathizer. The Democrats also produced a pamphlet, based on internal government documents, that highlighted the extra pay that Scott had received for special assignments, including drafting those new army regulations. The publication implied that Scott had abused his army position for financial gain.

Scott lost in a landslide, capturing only four states and just 42 electoral votes out of 296. In his memoirs, Scott devotes just a few paragraphs to the election, calling it his greatest humiliation and largely blaming it on Whig divisions. The election was devastating to the party, which never nominated another presidential candidate. Several years later, former Whigs, including Greeley, Seward, and Abraham Lincoln, formed the Republican Party.

After the election, Scott’s New York friends again rallied around him. A group led by Senator Hamilton Fish bought the general a brownstone on 12th Street between Fifth and Sixth Avenues. Scott, who had resided in Washington during the campaign, once more retreated to New York, fed up with politics and desperate to avoid daily commerce with the new administration of Democrat Franklin Pierce.

History had one more role for Scott to play. In November 1860, a divided country elected Lincoln president, and talk of secession among Southern states intensified. On December 12, the commanding general boarded a train for the capital so that he could oversee security at the presidential inauguration in March, and he took with him the headquarters of the United States Army. Seven states seceded from the Union over the next two and a half months, while an increasingly worried Scott got word of plots against Lincoln and threats against himself. “The inauguration of President Lincoln was, perhaps, the most critical and hazardous event with which I have ever been connected,” Scott observed. “In the preceding two months I had received more than fifty letters, many from points distant from each other—some earnestly dissuading me from being present at the event, and others distinctly threatening assassination if I dared to protect the ceremony by a military force.”

On Inauguration Day, rather than sit among the notables on the dais, Scott remained planted in his coach on the northern side of the Capitol, ready at a moment’s notice to command the federal forces on duty. Keyes, his aide, wandered the crowds in plainclothes. “The election having been entirely regular, I resolved that the Constitution should not be overturned by violence if I could possibly prevent it,” wrote Scott.

As the country careened toward war, Scott suffered one of the greatest disappointments of his life. He immensely admired Robert E. Lee, whom he had watched grow into an exemplar of the West Point spirit. Scott recommended to Lincoln that, if war broke out, Lee should assume field command of the army. But just days after Virginia seceded, Lee sent Scott a letter in which he resigned from the army. “Save in the defense of my native State, I never desire again to draw my sword,” wrote Lee. The same day, a delegation of Virginians visited Scott, urging him to join their cause; Scott turned them down.

As many of its top officers followed Lee’s example, the federal army was ill-prepared to bring the rebel states to heel. In July 1861, two Confederate armies crushed federal forces at Bull Run near Manassas, Virginia, provoking panic in Washington. Though Scott wasn’t in the field, he took responsibility for the defeat. Lincoln then appointed a personal favorite, George McClellan, to take command of the Army of the Potomac, the main federal force around the capital. On October 31, Scott, recognizing at 75 that he was no longer capable of leading the army, resigned as commanding general, allowing Lincoln to give McClellan command of the entire federal force. A few days later, the old general boarded a train to return to New York City.

Scott lived long enough to see a succession of Union commanders fall before Mexican-American War campaigners such as Lee, Stonewall Jackson, and James Longstreet, until a little-known lieutenant from the same campaign, Ulysses S. Grant, arose to lead the Union to victory. Grant’s victory gave Scott a last triumph. Scott had devised a plan to defeat the South dubbed “Anaconda,” which proposed blockading the Mississippi River and encir- cling the South so as to squeeze it into submission. Though McClellan ignored Anaconda, Grant and General William Tecumseh Sherman employed a version of the strategy to overcome the South at last.

After the war, Grant visited Scott, paying one more tribute to the old soldier. About a year later, on May 29, 1866, Scott died at West Point, where he is buried next to his wife. Grant and a host of other generals journeyed to his funeral. Around the country, flags flew at half-mast. In Manhattan, the New York Stock Exchange closed for the day.

Yet Scott has wound up “on the shelf” of American history. Today, few discuss the campaign that he fought so expertly in Mexico—part of an unpopular war dismissed by some critics as little more than a United States land grab. A generation of officers whom Scott helped train are now better remembered for the war that they fought against one another than for the battles that they undertook alongside him. Even in the city that once worshiped him, few signs of Scott’s long residence remain. A small plaque remembering him adorns the brownstone on West 12th Street, which New York University now owns. A portrait of Scott by Miner Kilbourne Kellogg hangs in City Hall; the New-York Historical Society owns a copy. Otherwise, the city that Scott knew so well has abandoned him.

Writing of Scott’s political difficulties, Hone observed that “republics are ungrateful.” He might have added that their great cities are forgetful.

Top Photo by The Print Collector/Getty Images


City Journal is a publication of the Manhattan Institute for Policy Research (MI), a leading free-market think tank. Are you interested in supporting the magazine? As a 501(c)(3) nonprofit, donations in support of MI and City Journal are fully tax-deductible as provided by law (EIN #13-2912529).

Further Reading

Up Next