A Family Divided: The Roosevelts and the Civil War

A House With Confederate Sympathies

The Civil War created a profound contradiction at the heart of the Roosevelt household on East 20th Street in Manhattan. On the surface, it was a Union family—Theodore Sr. sympathized with the Union cause and opposed slavery on principle. But that surface concealed a deeper complexity. Mittie, Theodore Jr.'s mother, was a Southern belle whose family was fighting for the Confederacy. Her brothers—James Dunwody and Irvine Bulloch—were not watching the war from the safety of the North; they were actively fighting for the Confederate cause.

Moreover, Mittie herself reportedly packed supplies for Confederate soldiers while living in the Union household in New York. It was a gesture of loyalty to her family that created unbearable tension in the home. How did you remain loyal to the Union while your wife was sending supplies to the Confederacy? How did you reconcile your moral opposition to slavery with your love for a woman whose family owned slaves? How did your children navigate the impossible contradiction?

The Maternal Uncles in the Confederate Navy

Young Theodore's uncles—his mother's brothers—were real presences in his life despite fighting for the other side. James Dunwody Bulloch, called "Uncle Jimmie," had been captain of a packet ship when the war broke out. He made his way south to assume secret duties as a Confederate naval agent, operating in the shadows of international diplomacy from England. There, he orchestrated one of the Confederacy's most audacious achievements: the construction and fitting out of the CSS Alabama, the famous Confederate raider that would prey on Union commerce throughout the war.

Irvine Bulloch, Mittie's youngest brother, was only 19 when he left the University of Pennsylvania to sign on as a midshipman in the Confederate Navy. Legend held that he fired the last shot in the famous engagement between the USS Kearsarge and the CSS Alabama off Cherbourg, France—though this claim, like many wartime stories, acquired significance through retelling.

For young Theodore, these were not abstract enemies or distant rebels. These were his uncles—men he knew, men his mother loved, men whose absence from the household was a tangible presence. The Bulloch family honor was tied to the Confederate cause, and Mittie's devotion to her family was absolute. Yet Theodore was growing up in a household that, outwardly at least, supported the Union.

Lincoln's Funeral: A Child's First Encounter with Loss and History

Theodore Roosevelt Jr. was six years old when Lincoln's funeral cortège passed through the streets of New York in April 1865. The impact on him is uncertain—children of six do not form clear memories—but we know from family accounts that he watched the procession from a window at his grandfather's mansion with his mother. Lincoln was dead—murdered—by those whom his mother's family supported. The contradiction was impossible to ignore, even for a young child. His mother stood beside him, watching the body of the murdered president pass through the streets of the city where her own brothers were fighting for the Confederate cause. For young Theodore, this was the Civil War made personal and real in a way that no adult explanation could achieve.

The funeral procession itself was extraordinary. Thousands of New Yorkers lined the streets. Minute guns were fired in salute. Military bands played solemn music. The city was transformed into a place of mourning and loss. Young Theodore absorbed the gravity of the moment, understanding, in the way that children do, that something profound and terrible had happened.

A Child's Impossible Contradictions

In the games that children played on the bridges in Central Park, the Roosevelt children worked through these contradictions in fantasy. Bamie would play the Rebel blockade-runner, daringly breaking through Union lines. Theodore would play a Union boat, attempting to enforce the blockade. They would enact these scenarios again and again, living out through play the impossible situation that defined their family life. It was a way of processing contradiction—of acting out the conflict that their household contained in a safely fictional context.

More tellingly, during evening prayers with his Aunt Anna Bulloch (Mittie's sister, visiting from the South), young Theodore would implore the Almighty to "grind the southern troops to powder." It's a remarkable prayer—the intensity of it revealing the depth of his conflicted feelings. How did he say such a thing while kneeling beside his beloved aunt? How did he reconcile asking God to destroy the army his family supported while simultaneously loving that family? The prayer suggests that the young boy understood, at some level, that the values his father represented—Union, the end of slavery—had to triumph, even if that triumph meant destruction of those he loved. It was a prayer that contained within it the full tragedy of his family situation.

Theodore Sr.'s Moral Compromise

The patriarch of the household faced his own impossible choice. Theodore Roosevelt Sr. was sympathetic to the Union cause and opposed slavery on principle. Yet he was also a man of his social class—wealthy, well-connected, expected to manage the war through financial support and charitable work rather than through personal military service. Very few men of his position were expected to fight; it was "simply not done" among New York's merchant class.

So Theodore Sr. made a decision that he would later view with deep regret: he hired a substitute—a legal though controversial arrangement that allowed wealthy men to pay another to take their place in the army. The sum was approximately $1,000, a sum far beyond what an ordinary wage earner could afford, representing perhaps ten to fifteen times its current-day equivalent in purchasing power.

It was a system that deeply troubled many people's consciences. When the Draft Riots exploded in New York in July 1863—largely in reaction to the inequity of a system that favored the rich—the anger was righteous. A system in which you could purchase exemption, in which the poor were drafted to die while the rich bought their way out, was fundamentally unjust. Theodore Sr. knew this. Mittie's mother, observing from the safety of a seaside hotel, noted with surprising fairness: "I do not wonder that the poor mechanics oppose conscription. It certainly favors the rich at the expense of the poor."

Yet Theodore Sr. tried to compensate through other service. Working with William E. Dodge Jr. and Theodore Bronson, he conceived of the Allotment Commission—a plan that allowed soldiers to send home part of their pay to their families without additional cost. The three men spent nearly two years traveling from regiment to regiment by train, boat, and horseback in all weather and seasons, convincing soldiers to participate in the program. It was his way of serving, even if he wouldn't fight.