Ulysses S. Grant, who graduated from the U.S. Military Academy at West Point in 1843, didn’t go there because he dreamed of being a soldier. The future Civil War general and two-term U.S. president went because, as he later recalled, his father “said he thought I would, and I thought so too, if he did.”

The Ohio-born tanner’s son was initially so unenthusiastic about military life that he followed the Congressional debates over West Point’s future that took place during his first semester, in hopes that the Military Academy would close and he could return home without embarrassment. Despite his deep ambivalence, Grant’s experiences at West Point and as a young officer provided both formal and incidental preparation for his later career and gave him insights into future Civil War comrades and foes.

He found military training ‘wearisome’—but loved novels

While critics would later exaggerate Cadet Grant’s poor performance, he actually graduated in the middle of his class (21st of 39), had an aptitude for math and displayed an unequalled proficiency in horsemanship. Owing to conduct demerits and a dismal “standing in all the tactics,” he served his senior year as a lowly private. His only leadership position was the presidency of the cadet literary society.

Surviving drawings and paintings from Grant’s West Point years show early signs of what the Prussian military theorist Carl von Clausewitz called a “special gift” common to successful painters and generals alike: namely, a remarkable visual memory. After Grant studied a map, his staff officer Horace Porter recalled, “it seemed to become photographed indelibly upon his brain.”

In his memoirs, Grant makes no secret of his lack of engagement with military training and academics. He describes the former as “wearisome and uninteresting” while noting of the latter, “I rarely ever read over a lesson the second time during my entire cadetship.” Instead, he spent much of his time “devoted to novels, but not those of a trashy sort.” Plunging himself into the imagined worlds of Washington Irving, James Fenimore Cooper and other popular 19th- century authors, Grant learned, as his biographer Jean Edward Smith suggests, an “appreciation for linguistic precision.” Yet he did not absorb the romantic view of war common to period fiction. About war he was a hard realist.

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Grant met old acquaintances later on the battlefield

Ulysses S. Grant in the Mexican War
VCG Wilson/Corbis/Getty Images
Grant at the Capture of the City of Mexico in the Mexican War of 1846-1848.

Commentators, as Smith points out, tend to exaggerate the significance of the relationships forged by West Pointers to their later careers. It wasn’t always easy to predict a peer’s eventual military success or failure. A number of the cadets who showed the greatest military promise in the years before the Civil War disappointed, while the less noteworthy, Grant among them, sometimes achieved beyond all expectation. But life at the academy was extremely isolated, furloughs rare and the corps quite small. Cadets would have been thrown into each other’s company in ways that would likely have exposed their response to adversity. In many cases, early impressions were cemented by service together in the Mexican War of 1846-1848. (The small size of the regular army all but guaranteed that perceptions—deserved or otherwise—would dog officers throughout their careers.)

What did his peers think about Grant? His reputation for drinking, which he probably did a fair measure of while separated from his family at a series of remote posts in the Pacific Northwest after the Mexican War, was widely circulated in army circles, and disparaging stories persisted throughout the Civil War. No one envisioned Grant as a future commander. As his good friend, the Confederate general James Longstreet noted, it was “to the surprise of many” that Grant turned out to be “the man for the times.” Nevertheless, acquaintances recognized early on what would become his distinguishing qualities: tenacity, loyalty and a sense of calm in the face of physical danger.

Grant, for his part, was a keen observer of human nature who believed that attending West Point at “the right time”—he encountered more than 50 future Civil War generals there—together with his experiences in Mexico, proved “of great advantage.” In addition to teaching “practical lessons,” the Mexican War introduced him to “older officers, who became conspicuous in the rebellion.”

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Grant explains the significance of his early acquaintance with those he opposed in the Civil War: “I do not pretend to say that all movements, or even many of them, were made with special reference to the characteristics of the commander against whom they were directed. But my appreciation of my enemies was certainly affected by this knowledge.” Brief but nuanced character sketches of men Grant knew at West Point or in Mexico enrich his memoirs. For example, he contrasts the “upright” but “irascible” Braxton Bragg, whom he defeated at the Battle of Chattanooga, with Longstreet, with whom he would resume his friendship after the war: “Longstreet was an entirely different man. He was brave, honest, intelligent, a very capable soldier...just and kind to his subordinates, but jealous of his own rights.”

With regard to Robert E. Lee, a commander so many “clothed” with “almost superhuman abilities,” Grant writes, “I had known him personally, and knew that he was mortal; and it was just as well that I felt this.”

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Grant and Simon Buckner: loyalty, betrayal and enduring regard

Simon Buckner
Duncan 1890/Getty Images
General Simon Bolivar Buckner was an American soldier and politician who fought in the United States Army in the Mexican–American War and in the Confederate States Army during the American Civil War.

Perhaps no relationship reveals the ways in which West Point connections informed Grant’s experience in the Civil War more clearly than does his acquaintance with Simon Bolivar Buckner. On Saturday, October 29, 1842, Grant’s name appears in the library circulation records next to a volume of Livy’s history of Rome. In the next column, Buckner’s is inscribed by a book about Napoleon. Neither could have predicted the ways their paths would intersect in the ensuing decades: on a hiking expedition up a volcano while on R&R in Mexico; in New York City, when Buckner lent Grant money to get home; on opposite sides of a battle for the Confederate-held Fort Donelson, Tennessee, in February 1862.

Buckner had been left in an impossible situation at Donelson by the departure of his two superiors and the escape of a cavalry detachment. But when he wrote to Grant to discuss surrender terms, the reply came: “No terms except an unconditional and immediate surrender can be accepted.” Clearly disappointed, Buckner responded: “The distribution of the forces under my command…and the overwhelming force under your command, compel me…to accept the ungenerous and unchivalrous terms which you propose.”

Grant described their meeting after the surrender with typical frankness and a touch of humor: “I had been at West Point three years with Buckner and afterwards served with him in the army, so that we were quite well acquainted. In the course of our conversation, which was very friendly, he said to me that if he had been in command I would not have got up to Donelson as easily as I did. I told him that if he had been in command I should not have tried in the way I did.”

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Donelson gave Grant his first taste of fame: The newspapers touted him as “Unconditional Surrender” Grant. Buckner, meanwhile, spent months as a prisoner of war.

Their relationship survived even this clash. And when Grant was dying in 1885, racing to complete his memoirs and trying to rescue his family from bankruptcy, Buckner was one of Grant’s last, most warmly received visitors—and he would serve as a pallbearer at his funeral. When journalists asked the departing Buckner what he and Grant had discussed, he demurred: “I cannot tell you… The visit was purely personal; and…it was too sacred.”

Tempting though it is to read this as a sentimental story about a war between brothers reconciled, the anecdote illuminates something of the elemental strangeness of this period in the history of West Point and the country. And it underscores the ways in which a confused intimacy—a delicate web of personal loyalty, betrayal and enduring regard—is woven throughout the national tapestry of the Civil War.

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Elizabeth D. Samet is the editor of The Annotated Memoirs of Ulysses S. Grant. Her books include No Man's Land: Preparing for War and Peace in Post-9/11 America. She is professor of English at West Point. This essay does not reflect the official policy or position of the Department of the Army, the Department of Defense or the U.S. Government.