Winfield Scott Winfield Scott ( June 13 , 1786 – May 29 , 1866 ) was a United States Army general , and unsuccessful presidential candidate of the Whig Party in 1852 . Known as " Old Fuss and Feathers " and the " Grand Old Man of the Army , " he served on active duty as a general longer than any other man in American history , and many historians rate him the best American commander of his time . Over the course of his forty - seven - year career , he commanded forces in the War of 1812 , the Mexican - American War , the Black Hawk War , the Second Seminole War , and , briefly , the American Civil War , conceiving the Union strategy known as the Anaconda Plan that would be used to defeat the Confederacy . He served as Commanding General of the United States Army for twenty years , longer than any other holder of the office . A national hero after the Mexican - American War , he served as military governor of Mexico City . Such was his stature that , in 1852 , the United States Whig Party passed over its own incumbent President of the United States , Millard Fillmore , to nominate Scott in that year ' s United States presidential election . At a height of 6 ' 5 " , he remains the tallest man ever nominated by a major party . Scott lost to Democrat Franklin Pierce in the general election , but remained a popular national figure , receiving a brevet promotion in 1856 to the rank of lieutenant general , becoming the first American since George Washington to hold that rank . Early years . Winfield Scott was born to William Scott ( 1747 – 1789 ) and Anna Mason ( 1748 – 1803 ) on Laurel Branch , the family plantation in Dinwiddie County , Virginia , near Petersburg , Virginia , on June 13 , 1786 . He briefly attended the College of William and Mary , studied law in the office of a private attorney , and served as a Virginia militia cavalry corporal near Petersburg in 1807 . Army captain . Scott ' s long career in the United States Army began when he was commissioned as a captain in the Light Artillery in May 1808 , shortly before his 20th birthday . Scott ' s early career in the army was tumultuous . Scott openly criticized the then Commanding General of the Army , James Wilkinson . Scott was court - martial ed for insubordination in 1810 and had his commission suspended for one year . Afterwards , Captain Scott served in New Orleans on the staff of General Wade Hampton from 1811 to 1812 . War of 1812 . Lieutenant Colonel at Queenston Heights . The army promoted Scott to lieutenant colonel in July 1812 . Scott served primarily on the Niagara Campaign front in the War of 1812 . He took command of an American landing party during the Battle of Queenston Heights ( Ontario , Canada ) on October 13 , 1812 . Most New York militia members refused to cross into Canada in support of the invasion , and the British compelled New York militia commander Brigadier General William Wadsworth and Scott , the Regular Army commander , to surrender . The British held Scott as a prisoner of war . The British considered Irish - American prisoners of war British subjects and traitors and executed 13 such Americans captured at Queenstown Heights . The British paroled and released Scott in a prisoner exchange . Upon release , Scott returned to Washington to pressure the Senate to take punitive action against British prisoners of war in retaliation for the British executions of Irish - American soldiers . The Senate wrote a bill after this urging , but President James Madison believed the summary execution of prisoners of war unworthy of civilized nations and so refused to enforce the act . Colonel at Fort George . Scott was promoted to colonel in March 1813 . Scott planned and led the capture of Fort George , Ontario , on the Niagara River . By crossing the Niagara and landing on the Lake Ontario shore , Scott forced the British to abandon Fort George . Colonel Scott was wounded in this battle , which is considered among the best planned and executed U . S . operations of the war . Brigadier General at Chippawa and Lundy ' s Lane . Scott was promoted to brigadier general on March 19 , 1814 . He was only 27 years old at the time ; one of the youngest generals in the history of the U . S . Army . General Scott earned the nickname of " Old Fuss and Feathers " for his insistence on military appearance and discipline in the Army , which consisted mostly of volunteers . In his own campaigns , Scott preferred to use a core of Army regulars whenever possible . Scott perennially concerned himself with the welfare of his men , prompting an early quarrel with General James Wilkinson over an unhealthy bivouac on land Wilkinson owned . During an early outbreak of cholera at a post under his command , Scott , alone among officers , stayed to nurse the stricken enlisted men . Scott commanded the 1st Brigade , and was instrumental in the decisive American success at the Battle of Chippawa on July 5 , 1814 . Scott had a major role in the bloody Battle of Lundy ' s Lane on July 25 , and suffered serious wounds . The American commander , Major General Jacob Brown , and the British - Canadian commander , Lieutenant General Gordon Drummond , were also wounded . Brevet Major General . For his valor at Lundy ' s Lane , Scott received a brevet ( i . e . an honorary promotion ) to major general to date from July 25 , 1814 . However , the severity of his wounds prevented his return to active duty for the remainder of the war . In 1815 Scott was admitted as an honorary member of the Pennsylvania Society of the Cincinnati in recognition of his service in the War of 1812 . Peacetime activities . After War of 1812 . Brigadier General Winfield Scott supervised the preparation of the first standard drill regulations for the Army and headed a postwar officer retention selection board in 1815 . He also served as president of Board of Tactics in 1815 . Scott visited Europe to study French military methods in 1815 / 1816 . He translated several military manuals of Napoleon I of France into English . Scott held regional command in the Division of the North in 1816 . He married Maria D . Mayo ( 1789 - June 10 , 1862 ) in 1817 . Scott served as president of the Board of Tactics in 1821 and 1824 . Scott commanded the Eastern Department in 1825 . Scott again served as president of the Board of Tactics in 1826 . The Army passed over Scott for army command ; in 1828 , he resigned , but the Army refused his resignation . Scott again visited Europe and then resumed command of the Eastern Department in 1829 . Upon direction of the War Department , Scott in 1830 published " Abstract of Infantry Tactics , Including Exercises and Manueuvres of Light - Infantry and Riflemen , for the Use of the Militia of the United States " for the use of the American militia . Indian Wars and Nullification Crisis . Cholera among his reinforcing troops prevented Scott from taking field command during the Black Hawk War . In late 1832 and early 1833 Scott served as an emissary from President Andrew Jackson to South Carolina during the Nullification Crisis . In 1832 , Scott replaced John E . Wool as commander of Federal troops in the Cherokee Nation lands in Georgia . Scott commanded the field forces in Second Seminole War and Creek War in 1836 . Scott was recalled to Washington due to the highly politicized nature of the tactics he employed and the huge expenditures incurred in policing the frontier , compounded by controversies between regular army and local militia officers . Brigadier General Edmund Meredith Shackelford was appointed commander in the area by President Jackson until Brigadier General Thomas Jesup could arrive . A court of inquiry later cleared Scott of wrongdoing in the Seminole and Creek operations . Scott felt that his recall was a political intrigue . In 1845 , Shackelford wrote to Jackson for a clarifying statement that Shackelford had had no part in Scott ' s recall to Washington . Scott assumed command of the Eastern Division in 1837 . Scott was responsible for maintaining order on the Canadian border , where the Patriot War threatened to entangle the U . S . in the Upper Canada Rebellion . Cherokee Removal . Presidents Jackson and Van Buren , ignoring the Supreme Court ' s ruling in " Worcester v . Georgia " , tacitly supported Georgia ' s expulsion of the Cherokees . In 1838 , Scott was placed in charge of enforcing the Treaty of New Echota , including removal of the Cherokees to the " Indian Territory " ( now Oklahoma ) . Van Buren put Scott in command of the " Army of the Cherokee Nation " , headquartered at Fort Cass and Fort Butler . Arriving at New Echota , Cherokee Nation , on April 6 , 1838 , Scott immediately divided the Cherokee Nation into three military districts . He designated May 26 , 1838 as the beginning date for the first phase of the removal . The first phase involved the Cherokees in Georgia . Scott wanted Army regulars rather than Georgia militia for this operation , because the militia had personal gains at stake ; some claimed Cherokee land . The promised regulars did not arrive in time , so Scott proceeded with 4 , 000 Georgia militia . The moral implications of the Jackson - Van Buren policies did not make Scott ' s role easy . Representative ( and ex - President ) John Quincy Adams opposed the removal , imputing it to " Southern politicians and land grabbers ; " many Americans agreed . Scott reassured the Cherokee people of proper treatment . In his instructions to the militia , Scott called any acts of harshness and cruelty " abhorrent to the generous sympathies of the whole American people . " Scott also admonished his troops not to fire on any fugitives they might apprehend unless they should " make stand and resist . " Scott detailed help to render the weak and infirm : " Horses or ponies should be used to carry Cherokees too sick or feeble to march . " Also , " Infants , superannuated persons , lunatics , and women in a helpless condition with all , in the removal [ deserve ] peculiar attention , which the brave and humane will seek to adopt to the necessities of the several cases . " Scott ' s good intentions , however , did not adequately protect the Cherokees from terrible abuses , especially at the hands of " lawless rabble that followed on the heels of the soldiers to loot and pillage . " At the end of the first phase of the removal in August 1838 , 3 , 000 Cherokees left Georgia and Tennessee by water toward Oklahoma , but camps still retained another 13 , 000 . By the intercession of Chief John Ross in Washington , these Cherokees traveled " under their own auspices , unarmed , and free of supervision by militiamen or regulars . " Though government contractors , steamboat owners , and others who stood to profit protested , Scott carried out this new policy . Ex - President Jackson demanded of the Attorney General the replacement of Scott and the arrest of Chief Ross . Within months , Scott captured ( or killed ) every Cherokee in north Georgia , Tennessee , and Alabama who could not escape . His troops reportedly rounded up the Cherokee and held them in rat - infested stockades with little food . Private John G . Burnett later wrote , " Future generations will read and condemn the act and I do hope posterity will remember that private soldiers like myself , and like the four Cherokees who were forced by General Scott to shoot an Indian Chief and his children , had to execute the orders of our superiors . We had no choice in the matter . " More than four thousand Cherokee died in this confinement before ever beginning the trip west . As the first groups herded west died in huge numbers in the heat , the Cherokee pleaded with Scott to postpone the second phase of the removal until autumn , and he complied . Determined to accompany them as an observer , Scott left Athens , Georgia , on October 1 , 1838 and traveled with the first " company " of a thousand people , including both Cherokees and black slaves , as far as Nashville . The Cherokee removal later became known as the Trail of Tears . Aroostook War . When Brigadier General Winfield Scott reached Nashville , superiors abruptly ordered him to return to Washington to deal with troubles on the Canadian border . On this assignment , he helped defuse tensions between officials of the state of Maine and the British colony of New Brunswick in the undeclared and bloodless Aroostook War in March 1839 . In 1840 , Scott wrote " Infantry Tactics , Or , Rules for the Exercise and Maneuvre of the United States Infantry " . This three - volume work served as the standard drill manual for the United States Army until William J . Hardee ' s " Tactics " , published in 1855 . Commanding General . On June 25 , 1841 the Commanding General of the United States Army , Major General Alexander Macomb , died . As he was the senior ranking officer in the Army , Scott was the obvious choice to succeed Macomb . Scott assumed office as commanding general on July 5 , 1841 and was promoted to the rank of major general , then the highest rank in the Army , with the date of rank of June 25 , 1841 . As commanding general of the Army , Scott took great interest in the professional development of the cadets of the United States Military Academy . Mexican - American War . Command appointments . During the Mexican - American War , Major General Scott was appointed by President James K . Polk to lead an army of Regular army and volunteer units to the Rio Grande for a quick campaign . Tensions between Scott and Polk developed , and Polk gave the command to Zachary Taylor . After Taylor ' s victory at the Battle of Monterrey much of Taylor ' s army was transferred to the Gulf coast for a proposed amphibious expedition against central Mexico . Polk wanted to appoint a fellow Democrat to command this expedition , and not a Whig , as if it succeeded the commander would be a strong candidate for President . The two ranking Democratic officers in the army were William O . Butler and Robert Patterson . Butler ' s capacity as an army commander was unknown , and Patterson was Irish - born , and not eligible to be President . Scott was a Whig , but he had the approval of members of Polk ' s cabinet and was given the command . Military campaigns . Landing at Veracruz , Scott , assisted by one of his staff officers , Captain Robert E . Lee , and perhaps inspired by William H . Prescott ' s " History of the Conquest of Mexico " , followed the approximate route taken by Hernán Cortés in 1519 , and assaulted Mexico City . Scott ' s opponent in this campaign was Mexican president and general Antonio López de Santa Anna . Despite high heat , rains , and difficult terrain , Scott won the battles of Cerro Gordo , Contreras / Padierna , Churubusco , and Molino del Rey . He then assaulted the fort of Chapultepec on September 13 , 1847 , after which the city surrendered . When the Duke of Wellington , victor of Waterloo , learned that Scott had succeeded against alarming odds in capturing Mexico City , he proclaimed Scott , " the greatest living general . " Saint Patrick ' s Battalion . A group of Irish - American deserters from the U . S . Army joined the Mexican army as the " San Patricio " ( St . Patrick ) Battalion . Seventy - two of them were captured at Churubusco . The San Patricio men were deserters in action , and had traitorously joined the enemy army . There was no question about this , and the punishment for desertion and treason was death . Scott ' s army was still facing a dangerous enemy and possible insurgency , so he placed the prisoners before courts martial to have them settle it . Eisenhower says the men were tried in two groups . The trials were conducted fairly by Brevet Colonel John Garland and by Colonel Bennet Riley . Because all the men captured were wearing Mexican uniforms , they were found guilty and sentenced to hang . This created a serious problem for Scott . He was troubled by the sweep of guilty verdicts . He did not want to alienate the Mexican public , who by now had made the deserters national heroes . Nor did he want to encourage insurgency among the Mexican people that would weaken his pacification program in progress . He also knew that the deserters were Irish - born Catholics , who had deserted Taylor ' s army because they allegedly felt mistreated and had witnessed atrocities " sufficient to make Heaven weep " against fellow Catholics , the Mexicans . Scott believed he needed to confirm the trials and sentences . He concluded that some men deserved less punishment , and sat up nights attempting to find excuses to avoid the universal application of capital punishment . In the end he approved the death penalty for 50 of the 72 San Patricios , but later pardoned five and reduced the sentence of fifteen others , including the ringleader , Sergeant John Riley . This left 30 slated for execution , 16 of whom were hanged on September 10 , 1847 . Four were hanged the next day , and the remainder assigned to Colonel William Harney for execution at some later date . On the day of execution , Harney ordered each deserter placed on a mule cart with a rope around his neck , fastening each rope to a mass gibbet . Then , during the battle of Chapultepec , just as the American flag was about to rise above the walls of the Mexican citadel , he ordered the executioners to give the mules a whack , causing the beasts to lurch forward , leaving the deserters in mid - air , dangling " en masse . " Some argue that this adversely affected Scott ' s record , as the events violated numerous Articles of War . Eisenhower , however , attributes the incident to Harney . During political intrigues later in his life , Scott ignored the events , stating " not one [ Irishman ] . . . was ever known to turn his back upon the enemy or friend . " Military governor . As military commander of Mexico City , he was held in high esteem by Mexican civil and American authorities alike , primarily owing to his pacification policy and fairness . For example , when he drew his " martial law order " to be issued and enforced in Mexico ( to prevent looting , rape , murder , etc . ) , all offenders , both Mexicans and Americans , were treated equally . Apart from his military career , Scott ' s vanity , as well as his corpulence , led to a catch phrase that was to haunt him for the remainder of his political life . Complaining about the division of command between himself and General Taylor , in a letter to Secretary of War William Marcy , Scott wrote of not wishing to " have a fire in his rear ( from Washington ) while he met a fire in front of the Mexicans . " This offended Marcy and also Polk . In another letter , Scott wrote that a letter from Marcy arrived as " at about 6 pm as I sat down to take a hasty plate of soup " . The Polk administration , eager to embarrass Scott , promptly published the letter , and the cryptic phrase appeared in political cartoons and comic songs for the rest of his life . Another example of Scott ' s vanity was his reaction to losing at chess to a young New Orleans lad named Paul Morphy in 1846 . Scott did not take his defeat by the eight - year - old prodigy gracefully . Scott was a charter member of the Aztec Club of 1847 , an organization of American officers who served in the Mexican War . Politics . Scott had been a possible Whig Party presidential candidate in 1840 and 1848 , but was passed over for other popular generals : William Henry Harrison and Zachary Taylor . In the 1852 presidential election , the Whig Party declined to nominate the incumbent President , Millard Fillmore , who had succeeded to the presidency on the death of Taylor . Seeking to repeat their previous successes with war heroes , the Whigs nominated Scott instead , who faced Democrat Franklin Pierce . However , the nomination process foreshadowed the general election : More grievously rent by sectional rivalries than the Democrats , the Whigs balloted fifty - three times before nominating Scott . The delegates then unanimously approved the platform except for the central plank that pledged " acquiescence " in the Compromise of 1850 , " the act known as the Fugitive Slave law included . " The plank carried by a vote of 212 to 70 , opposition coming largely from Scott ' s supporters . The old soldier , faced with disarray in the Whig ranks , sought out to resolve his dilemma by announcing , " I accept the nomination with the resolutions annexed . " To this , antislavery Whigs rejoined , " We accept the candidate , but we spit on the platform . " Scott ' s anti - slavery reputation undermined his support in the South , while the Party ' s pro - slavery platform depressed turnout in the North , and Scott ' s opponent was a Mexican - American War veteran as well . Pierce was elected in an overwhelming win , leaving Scott with the electoral votes of only Massachusetts , Vermont , Kentucky and Tennessee . Despite his defeat in the election , Scott was still a popular national hero . In 1855 , by a special act of Congress , Scott was given a brevet promotion to the rank of lieutenant general , making him only the second person in U . S . military history , after George Washington , to hold that rank . In 1859 , Scott traveled to the Pacific Northwest to settle a dispute with the British over San Juan Island , which had escalated to the so - called Pig War . The old general established a good rapport with the British , and brought about a peaceful resolution . Civil War . When the American Civil War began in the spring of 1861 , Scott was 74 years old and suffering numerous health problems , including gout , rheumatism , and dropsy . He was also extremely overweight and unable to mount a horse or review troops . As Scott could not lead an army into battle , he offered the command of the Federal army to Colonel Robert E . Lee on April 17 , 1861 ( Scott referred to Lee as " the very finest soldier I ' ve ever seen " ) . However , Virginia left the Union on that same day . Lee , though disapproving of secession , was hesitant at the possibility of taking up arms against his home state and asked if he could keep out of the war . Scott replied " I have no place in my army for equivocal men . " Lee then resigned and went south to join the Confederacy Although Scott was born and raised in Virginia , he remained loyal to the nation that he had served for most of his life and refused to resign his commission . The command of the Federal troops at Washington was given to Brigadier General Irwin McDowell . At this time , public opinion throughout the North called for an immediate campaign to crush the rebellion quickly . Scott considered this wrong - headed and probably impossible . Instead , he drew up a plan to defeat the Confederacy by blockading Southern ports and sending an army down the Mississippi Valley . Scott ' s scheme was derided as the " Anaconda Plan " , intended to crush the Confederacy slowly ; eventually the actual Union victory followed its broad outlines . But in July 1861 , the pressure to march " Forward to Richmond " was overwhelming . Lincoln set aside Scott ' s plan and directed McDowell to attack in Virginia . When Lincoln received news that the Union Army had been defeated at Manassas on July 21 , 1861 he went to Scott ' s residence . Scott assumed responsibility for the Union defeat . General George McClellan took command of the army at Washington ( now the Army of the Potomac ) . Scott ' s physical infirmities cast doubt on his fitness for command ; his weight had ballooned to over 300 lbs , In a play on his old nickname , he was called " Old Fat and Feeble . " He also ran into conflict with President Lincoln and others who wanted to organize the army into divisions . Scott argued that in the Mexican War , no commands larger than brigades had been needed , and that none were needed now , even though the Army of the Potomac was more than triple the size of Scott ' s army in Mexico . McClellan , the ambitious new field commander , wanted Scott out , and had many influential political friends . Scott resigned on November 1 , 1861 . McClellan then succeeded him as general - in - chief . Although officially retired , Scott was still occasionally consulted by Lincoln for strategic advice during the war . General Scott lived to see the Union victory in the Civil War in April 1865 . Shortly after the war ' s end , he joined the Military Order of the Loyal Legion of the United States ( MOLLUS ) , an organization of Union officers who had served in the Civil War . Scott received MOLLUS insignia number 27 . He died at West Point , New York on May 29 , 1866 and is buried in West Point Cemetery . Legacy . Scott served under every President from Jefferson to Lincoln , a total of fourteen administrations . Scott served a total of 53 years of active service as an officer - including 47 years as a general . Scott is one of a very few American officers who have served as a general in three major wars . ( The others are Douglas MacArthur and Lewis B . Hershey . ) Historians rank Scott highly both as a strategist and as a battlefield commander . Scott ' s papers can be found at the William L . Clements Library at the University of Michigan at Ann Arbor , Michigan . Scott County in the state of Iowa is named in Winfield Scott ' s honor , as he was the presiding officer at the signing of the peace treaty ending the Black Hawk War ; Scott County , Kansas , Scott County , Virginia Scott County , Minnesota , Scott County , Iowa , Scott County , Tennessee , Winfield , Illinois , Winfield , Indiana , Winfield , Alabama , were also named for him . Fort Scott , Kansas , a former Army outpost , was also named for him , and the towns of Scott Depot and Winfield in West Virginia . Scott Township in Mahaska County , Iowa , was formerly called Jackson before residents formally petitioned to change the township ' s name in light of their strong support of Scott in the 1852 presidential campaign . In addition , Cerro Gordo County , Iowa , and the town of Churubusco , Indiana , were named for battles where Scott led his troops to victory . Lake Winfield Scott , near Suches , is one of Georgia ' s highest elevation lakes . Mount Scott ( Oklahoma ) was named after Winfield Scott by Captain Randolph B . Marcy in 1851 . In 1882 , the fort now known as Fort Point at the foot of the Golden Gate Bridge in the Presidio was given the name " Fort Winfield Scott " by U . S . Army Headquarters . That fort officially retained the name until 1886 , when the fort was downgraded to a sub - post of the Presidio of San Francisco . The name was then used once again for the new coast artillery post established in 1912 in the Presidio . A paddle steamer named the " Winfield Scott " launched in 1850 and the US Army tugboat currently in service is named " Winfield Scott " . The General Winfield Scott House , his home in New York City during 1853 – 1855 , was named National Historic Landmark in 1973 . The saying " Great Scott ! " may have originated from a soldier under Winfield Scott . The Scott ' s Oriole was named for him by Darius N . Couch , a major general . It had turned out that the species was described several years earlier by naturalist Charles Bonaparte , but Scott ' s name was retained in the common name anyway . Union General Winfield Scott Hancock , Confederate General Winfield Scott Featherston and Admiral Winfield Scott Schley were named after General Scott . The actor Stuart Randall played Scott in the 1960 episode " The Quota " of NBC ' s " Riverboat " western television series . Retired United States Supreme Court Justice Sandra Day O ' Connor is a descendant of Winfield Scott . Scott on U . S . Postage . General Winfield Scott is one of very few US Army Generals to be honored on a US Postage stamp . He was the first General to appear on a postage stamp after Washington , who was portrayed as a general on an . The first Winfield Scott stamp issue was released to the public in 1870 , four years after the General ' s death at West Point . The engraving depicts Scott in classic profile with an arc of 13 stars overhead and allegorical military weaponry at the bottom of the design . Because of the higher denomination of 24 - cents , which was a considerable sum for a postage stamp in 1870 , the stamp only had a printing of a little more than one million . Consequently surviving examples of this stamp are very scarce and quite valuable today . General Scott was honored again on the , one in a series of five commemorative stamps honoring notable Army heroes where Scott is depicted along with Andrew Jackson on the 2 - cent stamp of this series . The Army and the Navy issues were very popular when released , had a much larger printing and examples of this issue are still somewhat common today .