A Friend to the End


The biblical book of Proverbs declares that “there is a friend who sticks closer than a brother.” Though rare, those friendships are strong enough to endure anything, even separation and possible fights. Over three thousand years ago, David, a future King of Israel, and Jonathan, the son of King Saul, had such a friendship. More recently, during the mid-nineteenth century, unbreakable bonds were formed among those who attended the United States Military Academy at West Point. The Civil War seemed to sever those ties, but the war’s conclusion revealed that those bonds remained intact. In one particular case, there was a future Confederate general who built a lasting kinship with a future Union general and American president. The Confederate would remain close to his one-time opponent throughout their lives. His name was General James Longstreet. This is the unlikely story of his steadfast friendship with Union General Ulysses S. Grant before, during and after the Civil War.

James Longstreet, from his very beginning, was a true son of the South. Given the nickname of “Pete” by his family, Longstreet was born in South Carolina in January 1821 to a family that traced its lineage back to Dutch immigrants. His early years were spent working on the family farm in northeastern Georgia and reading about military heroes. He dreamed of becoming a soldier. To provide his son with the opportunity, his father enrolled him in the Richmond County Academy in Augusta, Georgia. He lived with his uncle and aunt in Augusta and, following the death of his father and the move of his mother to Alabama, stayed with them full time. Through the influence of a relative who was a Congressman from Alabama, Longstreet received an appointment to the United States Military Academy at West Point. It would be at West Point where he would make the most valued friend of his entire life.

Entering West Point in July 1838, James Longstreet soon found himself forming close bonds with men who would play a critical role in his future military career. His academic and disciplinary record at West Point was less than desirable. He consistently ranked near the bottom of his class in every subject, even initially failing one of his examinations in mechanics. Despite his poor performance, his greatest success came in the relationships he developed with those who would later become his comrades and adversaries in the Civil War. Among his future opponents, he befriended future Union Generals George H. Thomas, who was an upper classman at the time, and William S. Rosecrans, who was his roommate at West Point. He would face both of them at the Battle of Chickamauga. He also befriended Union General John Pope, whom he defeated at the Battle of Second Manassas or Bull Run. Among those who would join him in Confederate service, he grew close to Lafayette McLaws, who would serve as a division commander under Longstreet at the Battle of Gettysburg. Longstreet’s strongest friendship, however, was with a young cadet from Ohio who graduated the year after him in 1843 and was destined to become the future commander of all the Union armies and President of the United States — Ulysses S. Grant.

Given the nickname of “Sam” by his friends in honor of his initials U.S., Grant appeared to be the opposite of Longstreet. Pete stood a towering and robust six feet two inches where Sam was only five feet eight inches. There was also a marked difference in their personalities. Pete was more carefree and eager to embark on adventures than Sam, who was more reserved in nature. Grant also differed from Longstreet in that he never desired to become a professional soldier. Neither man let these differences keep them apart. Sam quickly proved that he was similar to Pete when it came to academics and military discipline. While better than Longstreet in most subjects, Grant remained only a mediocre student. His best subject was mathematics; he even wanted to stay at West Point as a mathematics professor after graduation. Grant also showed he was like Longstreet in his ability to accumulate demerits, once receiving one for not attending church. The two men also shared an interest in and love of horsemanship. Grant and Longstreet were also drawn together by the fact that they had relatively low rankings at the time of their graduations. Longstreet was fifty-fourth out of fifty-six, and Grant was twenty-first out of thirty-nine. The two forged an iron bond at West Point. Longstreet later described Grant as a man “of noble, generous heart, a lovable character, [and] a valued friend.” Their friendship only strengthened in the years after they left West Point.

After graduating in 1842, Longstreet was commissioned a second lieutenant and was posted with the Fourth Infantry at Jefferson Barracks, Missouri, ten miles south of St. Louis. He was soon engaged in the typical duties of drilling, training and inspecting his soldiers while at the same time falling in love with the daughter of his commanding officer. As at West Point, he made friends with many of his contemporaries, some of whom he would fight against during the Civil War. To his great delight, Sam joined him at the post in September 1843. In their free time, the two young officers toured the nearby countryside and attended various social events. One of their visits was to the home of their classmate and distant Longstreet relative, Fredrick T. Dent. One of those who warmly greeted Pete and Sam was Longstreet’s fourth cousin, seventeen-year-old Julia Dent. Grant was instantly smitten with Julia, and the two soon fell in love.

Not long after introducing Grant and Julia, Longstreet was transferred to the Eighth Infantry. In late 1845, he and the regiment were moved to Corpus Christi, Texas as American forces gathered for possible war with Mexico. At Corpus Christi, he was once again reunited with Grant, and the two friends spent the next few months together. To escape the monotony of camp life, the two often embarked on hunting expeditions for turkeys, deer and other wildlife. They also played poker, though Grant only participated when there was little money involved. Soon the men found themselves in the midst of the U.S.-Mexican War. After serving under General Zachary Taylor in northern Mexico, both Grant and Longstreet became part of General Winfield Scott’s advance and subsequent attack on Mexico City. One of those attacks was made against the fortress of Chapultepec, a charge in which Longstreet was wounded while carrying the national flag.

After recovering, Longstreet returned to the United States where he married his own sweetheart before attending the wedding of Sam Grant and Julia Dent, as the best man according to some. Over the next few years, the two had few occasions to reconnect. One of their reunions occurred in 1858 when Longstreet stopped in St. Louis on his way to a posting as a paymaster at Fort Leavenworth, Kansas. He learned that Grant had left the Army and had fallen on hard times. Nevertheless, Grant insisted on giving Longstreet a five-dollar gold piece as repayment for five dollars Longstreet had loaned Grant when they were cadets at West Point. Grant told Longstreet he could not bear being in debt to him. It soon became apparent though that the two friends would be separated by war.    

As the Civil War approached and then broke out, the two friends found themselves on opposite sides of the struggle. Joining the South, Longstreet rose to command the First Corps of the Army of Northern Virginia under Robert E. Lee while Grant rose to national prominence as commander of all the Union armies. Between the two of them they wore a total of six stars. Even when facing each other in battle, neither lost their respect or affection for the other. In the last part of the war, the two friends finally met on the battlefield as they fought throughout northern Virginia. On April 10, 1865, the day after Lee had officially surrendered, Longstreet was named a member of the surrender commission. Upon arriving at the location, he saw his old friend standing with the Union commissioners. Grant moved toward him and embraced Longstreet like a long-lost brother and joked about playing a game of poker like they had when they were younger. The war was over, and the two were together again.

In the years that followed, Longstreet became head of an insurance company, but his outspoken support for the Republican Party, including Grant’s bid for president, alienated him from his fellow Southerners. In an effort to help his friend out, Grant procured a job for him as the surveyor of customs in New Orleans, Louisiana. Longstreet’s new position and continued support for Grant and for certain Republican policies brought more vilification down on his head and eventually forced him to leave Louisiana for his native Georgia. He continued to serve in national politics as U.S. Minister to Turkey under Presidents Rutherford B. Hays and James A. Garfield and as U.S. Commissioner of Railroads under President William McKinley. In July 1885, upon learning of the death of Sam Grant, Longstreet paid him one of the greatest compliments a person could receive. He said that Grant “was the truest as well as the bravest man that ever lived.” In silent testament to their lasting friendship, Longstreet was present at the dedication of Grant’s tomb in New York City in 1897. On January 2, 1904, James “Pete” Longstreet and Ulysses S. “Sam” Grant were finally reunited in eternal peace.

James Longstreet’s lifelong friendship with Ulysses S. Grant demonstrated that there are some relationships that can endure anything. Their friendship was tested by fire, yet it came out steadfast and strong. The two never let go of the affection they held for one another, not even when they were honor-bound to try to destroy each other’s army. They underwent trials and tribulations, but, like David and Jonathan of old, they never failed to support each other and did what they could to ease the difficulties. They understood that was what true brotherhood meant. If ever there was a person who embodied the spirit of the proverb of a “friend who sticks closer than a brother,” it was James Longstreet and his indestructible bond with Ulysses S. Grant.


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2 responses to “A Friend to the End

  1. Eric Brown

    A great story Jake. True friendship endures all hardships and this is a relationship I was unaware of. Thanks for sharing it with us.

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