West Point and the Civil War

Richard Lawson Singley
16 min readFeb 3, 2020

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Surrender of General Lee to General Grant at Appomattox Court House

Many scholars of military history call the first two decades before the Civil War the “Golden Age” of West Point. Indeed, it was a transitional period from civilians that were directly commissioned and rose through the ranks into a professionally trained army. By the beginning of the Civil War, 75 percent of the officers were West Point graduates. The Civil War is often referred to as the first modern war. It was the largest war ever fought in the Western Hemisphere and it established the military traditions of West Point.

West Point

Located on the high west bank of New York’s Hudson River and established by Thomas Jefferson in 1802, West Point was the site of a Revolutionary-War fort built to defend the Hudson River Valley from British attack. The commander of the fort was Benedict Arnold, America’s most notorious traitor. Under his command was another famed American, Aaron Burr, who later was also labeled a traitor.

West Point fortifications 1780

West Point was conceived to be more than the nation’s military institution. Jefferson was a man of science and he appointed Ben Franklin’s grandnephew, Major Jonathan Williams, as the first superintendent with the instructions to emphasize science. Over the years, West Point had one of the best engineering schools in the world and it was from these seeds that the military tradition of the United States was established.

There was a cadet appointed from each congressional district along with some at-large appointees. Although all cadets were treated equally and abided by the same set of rules, some had advantages over others. Those from affluent families and educated at private schools such as McClellan and Lee were better prepared academically than those such as Grant and Stonewall Jackson that received only a basic education. Throughout the years, the curriculum and tradition of West Point matured.

The academy was somewhat modeled after the French in general and Napoleon in particular. So much so that French was a required course for at least the first two years so that American officers could converse with French officers. Although in existence for decades, it was at the onset of the Mexican-American War that West Point began to come of age.

By the time of the Civil War, many of its cadets had been seasoned by the Mexican-American War. They had shed blood together on the battlefields as brothers of a sacred fraternity of men bound together by a Revolutionary War fort transformed into an institution of higher learning and honor. West Point made the Civil War, and the Civil War made West Point.

Because of the emphasis of professional soldiers, both the North and the South sent their future military leaders to this distinguished military academy. The military and engineering prowess displayed during the Civil War would become part of the culture ingrained in the nation. West Point was a revolving door, where every four years new bonds were formed that became links in a chain of brotherhood that stretched for decades.

Friendship was also stretched across the blue and the gray as fellow West Pointers and comrades of the Mexican-American War were divided by the war. To what extent friendships both severed and maintained impacted the war effort is a question still unanswered.

Duty, Honor, Country — those hallowed words were ingrained in every cadet, but they struggled with which country that they would be loyal to. Secession came at a high price for the cadets and graduates of this noble military institution as many of them were forced to choose sides. This was extremely difficult to do amid an environment that thrived off comradeship and duty to each other. Few of them wanted war, but all would answer the call of duty if necessary. Although the enemy of my enemy is my friend has proven to be a wartime aphorism, in this case, the Civil War created enemies that had mutual friends and were friends among each other. The breakup of the band of brothers at West Point initiated a schism, not between maternal but fraternal brothers.

The Civil War

Unlike the Greek Peloponnesian War, which has gone down in the annals of history as the quintessential civil war, the Athenians and the Spartans had fought together against the Persians, but they did not train together. Therefore, personal relationships did not develop among the soldiers on opposite sides. On the contrary, from the beginning of the American Civil War, friendships were broken by an ideological line drawn in the sand that separated the North from the South.

The Civil War started with one West Pointer firing on another. On April 12, 1861, at Fort Sumter in Charleston, South Carolina, General P.G.T. Beauregard (Class of 1838), the former but temporal superintendent at West Point, attacked the Union commander at Fort Sumter Major Robert Anderson (Class of 1825), an Academy graduate who was an artillery instructor at West Point. Among Anderson’s students were Beauregard (who became his assistant), Sherman, Bragg, McDowell, Meade, Hooker, and Early.

Fort Sumter 1861; flying the Confederate Flag

Furthermore, the men at West Point, for the most part, were taught by the same instructors in the strategies and tactics of war and it was not unusual for former cadets to oppose their instructors and former superintendents on the battlefield. For example, at the battle of Gettysburg, Union Brigadier General Henry J. Hunt later criticized the firing of one of his Confederate students and stated that his firing did not do justice to his instruction.

Ulysses Simpson Grant, 18th president of the United States

Ulysses “Sam” Grant (Class of 1843) and James “Pete” Longstreet (Class of 1842) were good friends at West Point. Grant was married to a distant relative of “Old Pete” as Longstreet would be later called. Longstreet went on to become Lee’s second in command and Grant, Lee’s nemesis. Yet, Longstreet and Grant remained close. One of the first things that the two did after Lee’s surrender was to meet together, not as enemies, but as friends. At the end of the war, Grant signed Longstreet’s name to a pardon list after Longstreet refused to sign citing: he had done nothing wrong in defending his state.

Another close friend of Grant’s was Simon Bolivar Buckner (Class of 1844) whose union with Grant was less pleasant as he was captured by Grant and became a prisoner of war. As the commanding officer at Fort Donelson, he asked Grant for terms of surrender, in which Grant replied those words that have echoed through history: “No terms except unconditional and immediate surrender can be accepted.”

General Custer and James Washington

Battlefields of war, although long for men, are short terrains for fate. And once again it brought former classmates together on opposite sides. General George Armstrong Custer (Class of 1861) captured James Washington one of his classmates at West Point and they were photographed with each wearing different uniforms. Custer was one of the most popular cadets at West Point and he accumulated near-record demerits while at the Academy. During the Civil War, his popularity continued with his fellow Union soldiers and Confederates alike. As surrender talks were ongoing between Lee and Grant, Custer was likewise united with his West Point friend Robert V. Cowan now a member of the Confederacy.

During a battle between Union and Confederates, Custer sent a message to one of his Confederate friends not to expose himself so much in battle for fear of his life. Custer, like Pickett, (Class of 1846) graduated last in his class, yet he was the only one from his class to become a general. What is most ironic is that cavalry tactics was one of his worst courses. He would become one of the youngest generals in the Union army and his commanding officer, Phil Sheridan (Class of 1853) admired him so much that he brought the table that Lee signed his surrender on and gave it to Custer as a sign of his appreciation.

A flamboyant soldier that designed his uniform, his post-Civil War demise at the Battle of the Little Big Horn still shines through the clouds of posterity. Custer loved the military and revered his time at the academy so much that he chose West Point as his final resting place.

There were some bonds of friendship that were not divided by the war. Early in the war, Sherman (Class of 1840) had helped to persuade one of his old West Point friends George Thomas (Class of 1840) a Virginian to abandon his state and to fight for the Union. Thomas paid a heavy price for his loyalty to the Union as he was ostracized by members of his family. As a child, Thomas’ family had to move because of events stemming from the Nat Turner rebellion and some of them never forgot it. Yet, Thomas “known as the Rock of Chickamauga” became one of the Union’s most successful and respected generals.

Jefferson Davis president of the Confederacy

Likewise, Robert E. Lee (Class of 1829) and Jefferson Davis (Class of 1828) were at West Point together and during the war, they shared a close relationship. Joseph E. Johnston was also in the same class as Robert E. Lee. Davis; however, disliked and distrusted Johnston, a person that Grant thought was one of the most competent Southern generals. Some historians say that the feud between the two started at West Point over a girl, others say it happened while Jefferson Davis was Secretary of War. One thing for certain is that the two did not like each other. Jefferson Davis was also at West Point with Albert Sydney Johnston (Class of 1826) and shared an amicable relationship with him. Yet, others parted peacefully and respectfully never to see each other again or to meet briefly on the field of battle. Robert E. Lee and George Meade (Class of 1835) faced each other at Gettysburg but were old friends from the Engineering Corps.

George Pickett (January 16, 1825 — July 30, 1875)

Just before the start of the Civil War, Winfield Scott Hancock (Class of 1844) who also fought at Gettysburg held a dinner at his house with his West Point and Mexican War friends that would soon join the Confederacy. Among the guests were George Pickett, Dick Garnett (Class of 1841), and Lewis Armistead. They would all meet again on the battlefield at Gettysburg. Hancock would be seriously wounded; Armistead and Garnett would be killed and Pickett’s charge would go down in history as the most failed blunder of Gettysburg if not the war. Pickett was also good friends with George McClellan and Stonewall Jackson who were also members of their West Point Class of 1846 as was Jesse Reno from which the city in Nevada derived its name.

George McClellan also known as Little Mac

Like many West Pointers, McClellan had other friends that wore the gray uniform as he and A.P. Hill (Class of 1847) were roommates and both dated the same woman who eventually became McClellan’s wife. McClellan would face his former roommate on the battlefields as the war turned friends into enemies. Also, good friends of Hill and McClellan at West Point were Henry Heth (Class of 1847) and Ambrose Burnside (Class of 1847). Burnside was popular with many Confederate soldiers. When he was blamed for the loss at Fredericksburg, many Confederates felt sorry for him. After the war, Heth, a Confederate General and Burnside had a lasting friendship. In fact, Burnside lent Heth money to get back on his feet.

Robert E. Lee had a propensity to place West Pointers and Virginians in command of his forces. After Stonewall Jackson died of a wound that resulted from being shot by one of his men, Lee divided his army into three corps with A.P. Hill, Longstreet and Richard Ewell (Class of 1854) as corps commanders.

Unlike McClellan, A.P. Hill was known for his courage on the battlefield and both Robert E. Lee and Stonewall Jackson in their delirium call for him on their deathbeds. McClellan would survive the war, but A. P. Hill would not be as fortunate. He died on April 2, 1865, less than a week before the war ended. He was the last Confederate West Point general to die in the war.

The West Point nepotism was apparent within Lee’s ranks and not all of the West Pointers got along. For example, Armstead was expelled from West Point for breaking a plate over the head of Jubal Early (Class of 1837). Both became generals in Lee’s army but the animosity between the two persisted during the Civil War.

Stonewall Jackson is consistently ranked among American top generals

Similarly, A.P. Hill did not care much for Stonewall Jackson. Hill compared Jackson to a slumbering volcano that might erupt and wreak havoc at any moment. Lee often had to serve as an arbitrator between his generals. Competition was also fierce among West Pointers. During the war, some underclassmen at the academy became superior officers to upperclassmen. Yet, West Point remained an exclusive club on both sides during and after the war. Some classes produced more generals than others. The class of 1846 was much like the later class of 1915, “The Class the Stars Fell On.” The senior cadets had felt the winds of war breeze by them as the War with Mexico started in that same year. For many of that class, it was indeed baptism by fire. Forty–four of fifty-eight graduates would go on to fight in the Civil War.

The classroom was one thing, but the battlefield was another. For example, Pickett who was last in his class proved to be a much better soldier than Charles Seaforth Stewart who was first in his Class of 1846. Stewart never became a general and like many of his classmates would eventually serve under George McClellan the cadet that finished second to him.

McClellan was viewed as the cream of the crop. Six classmates served under him in the Army of the Potomac as generals: Reno, Couch, Seymour, Sturgis, Stoneman and Gordon. Four fought against him as generals in the Army of Northern Virginia: Jones, Wilcox, Pickett and Jackson (A.P. Hill fell to the class of 47 because of an illness). Of the future generals in other classes at West Point during McClellan’s years there, 19 served under him including Franklin, Burnside, Hancock, Smith, Stone, Gibbon and Pleasonton.

This class fought in three wars and produced 20 generals. Also, at the academy around that time were: Longstreet (Class of 1842), Sherman (Class of 1840), Grant (Class of 1843), William B. Franklin (Class of 1843) Richard Ewell, (Class of 1840) George Thomas (Class of 1840) and William Rosecrans (Class of 1842).

Grant’s class of 1843 also produced 20 generals although they were not as distinguished as the class of 1846. Most of these men served together in the Mexican-American War or the Indian Wars of the 1850s where bonds of friendship were further enhanced.

James McPherson(November 14, 1828 — July 22, 1864)

There were bonds of friendship of which war or time could not shatter. For instance, James McPherson (Class of 1853) graduated number one in his class and was the protégé of Sherman and Grant. Generals on both sides were deeply saddened by his death. Grant stated, “In his death the army lost one of its ablest, purest and best generals.” Sherman echoed these sentiments when he stated, “I have seen [McPherson], in danger, in battle when every muscle and every tissue was in full action, when his heroic qualities shone out as a star in the darkest night.”

Confederate General John Bell Hood (Class of 1853) the opposing general was a classmate and roommate of McPherson. McPherson, a brilliant student, tutored Hood and helped him get through West Point. Hood lamented:

“I will record the death of my classmate and boyhood friend, General James B. McPherson, the announcement of which caused me sincere sorrow…the attachment formed in early youth was strengthened by my admiration and gratitude for his conduct toward our people in the vicinity of Vicksburg.”

McPherson was one of those rare people that was not only a good student and soldier but also exhibited those rare charismatic traits of leadership that would have made him a promising political figure. McPherson Square in Washington DC is named in his honor. It is important to note that all of the outside Civil War statues in Washington DC are monuments of Union soldiers — with the exception of Albert Pike who does not appear in uniform and is honored for his contributions to Freemasonry and not his actions during the Civil War.

Philip Sheridan (Class of 1853) and John M. Schofield (Class of 1853) were also classmates of McPherson. Moreover, any cadet at West Point between the years of (1852–1855) would have had Robert E. Lee as their superintendent. As superintendent, Lee almost expelled Hood from West Point. Lee, like McPherson and McClellan, was an exemplary student graduating second in his class. While a cadet at West Point, Lee did not receive one demerit, a record that cannot be broken. In the minds of many of the cadets that went off to war, both North and South, Lee was the soldier’s soldier. Such was the indelible stamps that West Point placed on its graduates.

Robert E. Lee, commander of the Army of Virginia

The degree of which friendships and relationships established before the war, impacted the actions of the Civil War, has not been calculated and may be incalculable. For example, did Jefferson Davis’ good relationship with Lee and dislike of J.E. Johnston impair his judgment? How valuable was the friendship between Lee and William Nelson Pendleton (Class of 1830) a clergyman, Virginian and West Pointer? Pendleton provided spiritual counsel to Lee. Even though as an artillery commander he was mediocre at best, he was someone that Lee could speak candidly with and reveal his emotions and inner thoughts. Likewise, if Thomas and Sherman were not good friends would Thomas have fought for the South?

The circumstances of this war made it unique as a good friend may have been your foe and your comrade someone that you detested because of relationships forged before the war. In, The Art of War, Sun Tzu wrote: “Know thy self, know thy enemy; a thousand battles, a thousand victories.” Grant said that his moves were often predicated by what he knew about his enemies and that some of the generals of the Civil War lost focus because of their relationships and split affinities during the war.

For instance, some of the Confederate West Pointers may not have liked the specter of treason that came along with secession, and some Union West Pointers may have believed in state rights but viewed secession as treason. If Lincoln was not immune to the personal sympathies of war, best exemplified by having his sister-in-law, a known Confederate sympathizer staying in the White House with him; how could he expect those on the battlefield that had friends on the other side not to be sympathetic to their friends? This was part of the fog of war that transcended the battlefield and into the homes and hearts of the American people.

During the Civil War, 286 West Pointers including 19 born in the North joined the Confederate ranks. It was truly a unique case of men being bonded by the fraternity of arms yet divided by the duty of war. Very few of the West Pointers wanted to see the disagreement between the North and the South come to war. In this regard, they were like children not wanting to see their parents’ divorce because they loved them both.

Few times in history have so many friends become enemies in such a short period, not because of their own doing, frailties or shortcomings but because duty pulled on them from different directions. The blood and treasure of the Civil War were painfully obvious. However, hidden amid the blood was the blood of family members and dear friends, forced into battle against each other by the fortunes of war. These are the invisible strings of the puppet master known as fate.

Time heals most wounds, yet the memories of the war and those friends that paid the ultimate price were invisible wounds undress by time. Such were the consequences of the Civil War that stretched, broke and bound the chains of friendship. After the war, there was union among West Pointers that fought on opposite sides. Some Confederates regretted raising arms against their country and others would fight for it again. Former Confederate Generals Joseph Wheeler (Class of 1859) and Fitzhugh Lee (Class 0f 1856) served in the Spanish-American War in 1898.

Sherman, the man that made Georgia howl

Sherman and J.E. Johnston, opponents during the war would become friends after the war. As part of the last surrender of the Civil War, Sherman, like Grant had done with Lee, offered Johnston friendly terms of surrender. They would meet again at Grant’s funeral to pay homage to their fellow West Pointer and former President of the United States. Johnston and Sherman along with Phillip Sheridan and Simon Bolivar Buckner were pallbearers at Grant’s funeral in 1885. Two were from the Union and two from the Confederacy.

J.E. Johnston would later be an honorary pallbearer at Sherman’s funeral. Amid torrent tears and pouring rain, he refused to wear a hat citing that Sherman would refuse to wear one if the situation was reversed. He caught a cold and was dead within a month. At the funeral of Confederate General Cadmus Wilcox (Class of 1846), there were four pallbearers from the Union and four from the Confederacy.

War is such a terrible thing. Yet, as terrible as it is, there is something unexplainable about war that bonds men in ways that only those that have experienced it could understand. It forces men to embrace the trust necessary to place their lives in another man’s hand. No sword ever forged could be made of the steel that bonds such camaraderie. It is well understood among them that each soldier owes the other a debt that neither could fully pay.

Uncommon valor, that is the willingness to sacrifice your life to save the life of another, like any good friendship is so precious, so rare and immune to color that it must be a gift from God. If there is anything beautiful in war, it is that it can bring out such qualities in men amidst the closest thing to hell experienced on earth.

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Richard Lawson Singley

Author, educator, historian, former engineer at General Electric. Interested in the origins of all things. Author of A New Perspective richardlsingley@gmail.com