In the second half of the 19th century, few Americans were better known—and revered—than the man whose face looks out today from the $50 bill. Ulysses S. Grant led Union troops to victory in the American Civil War, then thwarted attempts by President Andrew Johnson to suppress fundamental civil rights of newly freed black Americans. Twice elected president himself, Grant stewarded a war-torn nation as it struggled to reunify. After leaving the White House, he invested his name and entire life savings to a Wall Street brokerage firm. It would make him rich, he was told, and afford him a comfortable retirement. Instead, it would leave him penniless.

Like any army commander, Grant had lost battles and had known the pain of defeat. But this loss hit personally. Never before had he found himself in straits so dire, literally destitute. Fortunately, the former president and retired general had one more fight in him—because his real troubles had just begun.

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Hiram Ulysses Grant was born in 1822 to Ohio tannery foreman Jesse Grant and his wife, Hannah. In 1839, Jesse secured a place for his son at West Point, not so much for its esteem as a military academy, but because it was free. On his first day there, the young man found his name listed by mistake as Ulysses Simpson Grant. He had always disliked his given initials—H.U.G.—so he came to rather like his new name with its patriotic abbreviation: U.S. Grant.

In 1843, at the age of 21, Grant began his career as a commissioned officer in Missouri, where he fell in love with his roommate’s sister, Julia Dent. They paused their courtship when Grant was sent to fight in the Mexican-American War, in which the U.S. took by force much of the current southwestern U.S. from its neighbor to the south. Personally, Grant felt opposed to what he saw as an unjustified use of superior military force, but he kept his political views to himself. He served dutifully as a junior officer and admired the qualities of General Zachary Taylor, which would shape his own leadership style in a much more significant war two decades hence.

Ulysses and Julia
Ulysses and Julia
Ulysses and Julia married just months following the end of the Mexican-American war in 1848, a joyous occasion for all but Grant’s parents. Staunch abolitionists, they liked Julia enough, but could not stomach her father, a slave owner and staunch defender of his right to be one. Grant’s parents boycotted the wedding.

Still, the couple’s mutual affection had not wilted in the five years they waited to wed, nor would it ever. To him, she would forever be “dear Julia”, and to her, privately, he was always “Ulys”. However, she would soon discover one small problem: her husband had a remarkable inability to earn a civilian living.

Like many of his peers in the Army, Grant took to moonlighting to bolster his meager military pay. But he failed at everything, in part from trusting everyone he met. He put his money into a venture to sell ice shipped in from the Arctic; it melted en route. Potatoes and onions, planted in anticipation of a certain windfall, rotted in the ground. His partnership in an establishment selling goods to soldiers, known as a sutler’s store, ended when he naively accepted a worthless IOU when his partner wanted out.

Grant began imbibing more than he should, which for him meant just two drinks. That’s all it took to intoxicate the young man to the point of insensibility. He usually resisted having a drink before reporting for duty, but not always. One day, his commander gave the drunken officer an ultimatum: resign or be kicked out. Grant chose to resign.

Broke, the Grants and their two infant children took up residence in a shack in Missouri. He peddled firewood on the streets of St. Louis to support his family, which soon included two more children. He pawned his gold watch to buy Christmas presents. When Julia Grant’s father died, they moved into the Dent family home. They also inherited something else—or rather someone else: a slave named William Jones.

Grant could have ended his financial woes by selling the man for a thousand dollars, or earned even more by renting him out. Instead, he took Jones to the local courthouse and signed manumission papers, setting him free. And then Grant went back to peddling firewood. He would later demur when asked why he did such a thing. Perhaps he was simply his father’s son.

At the outbreak of the Civil War, Grant wanted back in the Army, but the Army wasn’t interested. His reputation as a drunkard preceded him. Eventually they did offer him a unit to lead, one nobody else wanted. The 21st Illinois Artillery was one of the rowdiest, least disciplined, and most troubled units in the Union Army. When Grant took command on 14 June 1861, the restless men were only two weeks from the end of their enlistment. They couldn’t wait to go home. Then they met Grant. At the end of June, nearly every man signed up for another three years. “We knew we had the best commander and the best regiment in the State,” remarked one of them.

Grant turned the unit around by demonstrating a leadership style borrowed from Zachary Taylor in the Mexican-American War, marked by thoughtfulness, decisiveness, simple orders, and—above all—humility. This, his soldiers admired most of all. Grant shunned ostentation, flamboyance, and even a commander’s uniform. He dressed like his men did and looked “plain as an old shoe,” according to one Army doctor.

Grant paid keen attention to detail and remembered everything. He was unafraid of taking risks, learned from his mistakes, and seemed to never tire. And he kept his drinking in check. Instead, he mostly took comfort from cigars. He knew not to be seen drinking, but nobody cared how much he smoked.

Grant, 1868
Grant, 1868
Ulysses S. Grant the failure became Ulysses S. Grant the towering general, regarded to this day as one of the best military leaders of all time. In addition to military prowess, he also became known for making the most of whatever he had. This caught the eye of President Abraham Lincoln, who had grown dismayed with one general after another—Winfield Scott, George McClellan, Henry Halleck—complaining they did not have enough troops, or supplies, or time. Grant just did his job.

Waging war was no easier for Grant than his predecessors, and more than once, it appeared the Confederacy might win the war. But Grant kept his wits about him; he’d listen carefully to every word of advice he was given, then quickly make up his mind and pen an order. He communicated more easily in writing than in speaking, and thus would write long into the night. But he always saved energy for a letter to his Julia. “I have been writing until my fingers are tired and therefore you must excuse haste and a bad pen,” he’d write. “Kiss the children for me. Ulys.”

Thus it was Grant whose smarts and stamina—and hard-won victories at places like Shiloh, Vicksburg, and Richmond—landed him across the desk from General Robert E. Lee at Appomattox Courthouse in April 1865, accepting the Confederacy’s surrender and bringing the Civil War to a close. For Grant and the nation, the feeling of relief, and hope for the future, was beyond description. But it would not last long.

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Abraham Lincoln thought the world of Grant. The feeling was mutual. Their wives, however, had mutual feelings of another sort. They did not get along. At times, Grant had to choose between his wife and the president, as when Lincoln invited the Grants out for an evening of leisure just days after Lee’s surrender. Grant’s wife would have none of it. So he manufactured an excuse about having to catch the next train north to visit their son. President and Mrs. Lincoln went out that evening without the Grants, taking a short carriage ride from the White House to Ford’s Theater to watch a play. There, John Wilkes Booth entered their box and assassinated Lincoln.

Grant would never forgive himself for begging off, certain that had he accepted the invitation, his bodyguards stationed outside the door would have stopped Booth. As lieutenant general of the U.S. Army he was entitled to armed protection around the clock. The president in those days was not.

Lincoln’s assassination came just five days after Lee’s surrender. Confederate sympathizers seized the opportunity to roll back many of Lincoln’s efforts to reunite the nation. Unfortunately, one of those sympathizers was his own vice president. Andrew Johnson had once been a senator from Tennessee, and Lincoln did not select him for his vice presidential running mate. He had left that to delegates to the 1864 Republican Convention, who put Johnson on the ticket in an effort to attract war-supporting Democrats. Now, unexpectedly occupying one of the most powerful offices on earth, the new commander in chief set out to influence the post-war national rebuilding effort known as Reconstruction. His top priority? Maintenance of white supremacy.

Grant (center left) depicted next to Lincoln, General Sherman (far left), and Admiral Porter (right)
Grant (center left) depicted next to Lincoln, General Sherman (far left), and Admiral Porter (right)
Grant continued serving as Johnson’s general in chief and, later, secretary of war. He found himself walking a fine line, on one hand obliged to obey orders, but on the other dismayed by Johnson’s disregard for the rights of newly emancipated slaves, or ‘freedmen’. Johnson derided the Fourteenth Amendment, refused to enforce measures of Congressional Reconstruction Acts, and fired General Philip Sheridan for seeing to the registration of thousands of black voters.

Congress fought back. Its members united in using every means at their disposal to protect the nation from a man they saw as an utter threat to the prospect of a reunified country. They liked Grant, who let his opposition to his boss be known. Congress even passed legislation essentially preventing the president from telling his war secretary what to do. Ultimately, on 24 February 1868, the House of Representatives voted for the first time ever to impeach the president of the United States. The Senate failed to eject Johnson from office by a single vote.

Four days later, Republicans met in Chicago to choose a nominee for Johnson’s successor. They nominated only one candidate: Grant. He won the votes of all 650 delegates on the first ballot. In November, he was elected the nation’s 18th president, vowing to realize Lincoln’s vision of a re-United States of America.

Grant is not generally remembered as a great president. By blocking Johnson’s attempt to all but undo the Civil War, however, some might consider him at least a very good one. His central mission was to protect “citizens of every race and color” and to ensure their “peaceful enjoyment of the rights guaranteed to them by the Constitution.” That struggle continued well after his time—indeed, to the time of this writing. But Grant allowed that struggle to at least get underway.