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“MY CAREER AS A CADET,” George Armstrong Custer wrote, “had but little to recommend it to the study of those who came after me, unless as an example to be carefully avoided.” He did not exaggerate. Custer was one of the worst cadets in the history of the U.S. Military Academy. He managed to graduate on June 24, 1861, but unlike most of the fledgling second lieutenants eager to receive their first assignments, Custer had to remain behind. He was under arrest.

Custer had received his appointment to West Point because of his dalliance with Miss Mary Holland. Custer was teaching in a one-room schoolhouse and boarding at the Holland home in Athens Township, Ohio. When her father discovered the romance, he told Custer to leave immediately. Custer found lodgings nearby and kept up his affair with Mary, declaring his love in letters and poems.

To Mary,
I’ve seen and kissed that crimson lip
with honeyed smiles o’erflowing.

Enchanted watched the opening
rose, upon thy soft cheek glowing.

Your true and faithful Lover,
Bachelor Boy.

Custer insisted he wanted to marry her, but he also wanted to expand his horizons far beyond rural Ohio. He had hoped to attend college, but his parents could not afford the tuition. There was a way out, however. West Point was free and it offered a world of excitement and glory.

The only hitch was that Custer needed the requisite congressional appointment. The local congressman was a staunch Republican, and Custer’s father was an equally staunch Democrat. No son of a Democrat was about to get the congressman’s support. Fortunately there was another influential Republican in the county—Mary’s father, who wanted the Custer boy far away. West Point would do very nicely.

At West Point, what Custer lacked in academic excellence, he made up for in popularity as a cadet who took delight in openly breaking rules, an impulsive mischievous streak that had been with him since he was a child. The local minister recalled young Custer as “the instigator of devilish plots both during the service and in Sunday school. On the surface he appeared attentive and respectful, but underneath the mind boiled with disruptive ideas.”

And at West Point his focus remained exactly what it had been as a youth, getting by with minimum study and maximum fun. While his grades put him at the bottom of his class by the time of graduation, he was definitely at the top in demerits. Before the end of the first summer session he accumulated 27, and over the next four years he would earn the distinction of receiving more demerits than any other cadet in his class.

The range of his misdeeds was wide and varied. He kept cooking utensils in his chimney, left piles of rubbish outside his tent, bombarded his friends with snowballs outdoors and chunks of bread inside. He kept a messy room and defaced the walls with pencil marks. He was cited for swinging his arms too vigorously while marching, for shouting at a corporal and being late for just about everything—parades, company formations, supper and breakfast. He even got demerits for having his hair out of uniform; he let it grow so long that he wore a wig to hide its non-regulation length. When that ruse was discovered, he went to the post barber and had his head shaved. Other cadets teased him for weeks, shouting in unison “Hair out of uniform.”

Custer’s pranks were not always detected. Like the time he stole a chicken. After the cadets were supposed to be asleep, Custer silently led a raiding party through the darkness past the guards to the home of an officer who kept chickens. They stole a bird, boiled it in the cooking utensils he kept illegally, and left a trail of feathers from the barracks to the trash bin. No one was ever punished for the deed.

He once asked his Spanish-language instructor how to say “class is dismissed” in Spanish. When the teacher spoke the appropriate words, Custer immediately rose and marched the class out of the room. Custer “had more fun, gave his friends more anxiety, walked more tours of extra duty, and came nearer to being dismissed than any other cadet I have ever known,” a classmate recalled.

Like many cadets, Custer frequented the notorious tavern called Benny Havens, about a mile away. There cadets could get whiskey, hot rum flips and Benny’s famous buckwheat cakes to augment their meager dining hall fare. When the whiskey had done its work, the inebriated young men would break into the rousing “Benny Havens, Oh!” set to the tune of “The Wearing of the Green.”

Come fellows, fill your glasses and stand up in a row.
For sentimental drinking, we’re going to go.
In the army there’s sobriety, promotion’s very slow,
So we’ll cheer up our hearts with choruses at Benny Havens, oh!
Benny Havens, Oh! Benny Havens, Oh!
We’ll sing our reminiscences of Benny Havens, Oh!

Custer’s luck waned a bit at the beginning of his third year, when he had to be treated for gonorrhea. He could have contracted it on summertime leave back in Ohio, but most biographers believe he probably got it from a prostitute in New York City, typically the source of such infections among cadets.

Despite his cavalier attitude toward rules and regulations, Custer possessed a paradoxical self-control that saved him from expulsion and was evident in the pattern of his demerits. Any cadet who received more than 100 demerits in six months was automatically expelled. Custer earned 90 citations in only three months but managed to restrain himself for the next few months without a single misdeed. He would let his grades and deportment sink to the lowest permissible level but then achieve just enough to pass. His closest call with demerits was 98 in a six-month period.

Early in his last semester at West Point, Custer and some of his classmates tried to beat the odds of passing a major examination by stealing the list of questions each professor had submitted to the examining board. They were caught and arrested, and all but Custer were expelled a few months before graduation. Once again, Custer’s luck had held.

Custer graduated from the academy having accumulated 97 demerits in his last six months, and the lowest final examination scores in the class. His most dismal showing was in the course on cavalry tactics.

After graduation on June 24, 1861, the other newly commissioned graduates left for Washington within the week. But on June 29, while Custer was acting as Officer of the Day overseeing summer camp for new cadets, two of them got into a fistfight. Other cadets tried to break it up, but instead of stopping the fight Custer shoved the others out of the way, saying the antagonists should have the chance to fight it out fairly. Custer did not see Lieutenant William Hazen approach as the boys flailed away at each other. Hazen stopped the fight and arrested Custer for failing in his duty to maintain order.

The following day Custer appeared before Commandant of Cadets Lt. Col. John Reynolds, who asked why he had not followed procedure and placed the new cadets under arrest for fighting. Custer gave a straightforward, candid and revealing answer. “The instincts of a boy,” he told Reynolds, “prevailed over the obligations of an officer of the guard.”

Custer’s court-martial—on charges of neglect of duty and conduct prejudicial to good order and military discipline, serious allegations for one who had barely begun his career—began July 5. If he were found guilty, there might be no career and no opportunity for the glory or fame Custer desired.

But his luck held. Although judged guilty, he received only a reprimand. Three circumstances worked in his favor. First, Hazen, the arresting officer on the scene, testified for Custer, telling the court-martial board he considered Custer to have generally displayed good conduct during his years at West Point. Hazen’s motive for this creative interpretation of Custer’s behavior is not known, but his flattering testimony helped immensely.

Second, the congressman who had granted Custer the academy appointment intervened on his behalf. Custer, or perhaps some of his classmates, had gotten word of the situation to the congressman, who might not have wanted to be seen as a poor judge of character by having one of his appointees (even the son of a Democrat) drummed out of the service. He urged the board to show leniency.

Third, and the most practical reason for leniency, was that by the summer of 1861 the Union Army had already lost so many West Point–trained officers to the Confederacy that it needed all the trained manpower it could get.

On July 18, 1861, Custer left West Point for Washington. The Custer boy was going to war, which he fought in his usual colorful, courageous and controversial fashion as a cavalry officer. He later confessed that he loved combat. “I would be glad,” he wrote to a friend, “to see a battle every day during my life.” In describing his experiences he added, “If you could but have seen some of the charges that were made! While thinking of them I cannot but exclaim ‘Glorious War.’”

And within a mere two years, at the age of 23, George Armstrong Custer, the rebellious cadet whose hair had been out of uniform, achieved the rank of brigadier general and became a hero to the nation. James Gordon Bennett Sr., the influential editor of the New York Herald, hailed Custer as “The Boy General With the Golden Locks.” Journalists throughout the Northern states blazoned his name in headlines. Calling him the “Boy General” was enough; everyone knew who they were talking about. A year later he was promoted to major general.

Custer’s fame grew as a soldier of enormous valor, personal courage, leadership and dash. With the help of the media who pursued him, while he in turn actively courted their attention, he was widely known as a colorful and charismatic figure, both in appearance and behavior. Wearing a velvet uniform, his long wavy blond hair doused liberally with oil of cinnamon, he rallied his men from the front, leading charge after charge, fulfilling the dreams of his childhood. His ambition to succeed and his hunger for glory and fame were being fulfilled. “In years long remembered with the past,” he wrote after the Civil War, “when I was merging upon manhood, my every thought was ambitious—not to be wealthy, not to be learned, but to be great.”

Psychologist Duane Schultz has written more than a dozen history books and articles, including Coming Through Fire: George Armstrong Custer and Chief Black Kettle. He is currently writing a book about Carl – son’s Marine Raiders of World War I.

Originally published in the November 2013 issue of America’s Civil War. To subscribe, click here.