Roosevelt Before the Charge: A Remarkable 1895 Letter That Foreshadowed a Presidency & San Juan Hill!
A Letter That Defines the Rough Rider
This fascinating 1895 letter stands out as perhaps the most vivid showcase of Theodore Roosevelt’s analytical mind and deep‑rooted passion for military history that we have ever encountered. Written during his tenure as U.S. Civil Service Commissioner (1889 to 1895), Roosevelt sends his cousin, Dr. John West Roosevelt, a U.S. Navy surgeon, a sweeping and remarkably detailed analysis of battlefield casualties across centuries… a four‑page masterclass that reads like the private notes of a military theorist.
Drawing on an encyclopedic command of both European and American conflicts, he moves confidently from Gettysburg, Shiloh, and Cold Harbor to the Crimean and Franco‑Prussian Wars, using these comparisons to illustrate evolving dynamics in discipline, tactics, and technology. His emphasis on training, morale, and weaponry as decisive factors in warfare reveals not merely a hobbyist’s curiosity but a fully formed military philosophy, one he would soon put into practice as a Rough Rider.
Even before he ever stepped onto a battlefield, Roosevelt was already thinking like a commander: studying how men break, how armies endure, and how leadership shapes outcomes. In all the Roosevelt material we have handled, few pieces announce the making of a war hero and future president as clearly as this one.
Roosevelt the Thinker: Military History as Foundation
Roosevelt’s fascination with military history was lifelong and deeply formative. As a child battling illness, he devoured books on historic battles and military leaders, finding strength in the stories of courage, discipline, and tactical brilliance. This intellectual foundation culminated in his first major work, The Naval War of 1812, published when he was just 23 years old, a book still respected today for its rigor and strategic insight.
The 1895 letter to his cousin is a continuation of this disciplined study, but it goes further. It is not written for publication or political purposes. It is a private and uncompromising analysis. Roosevelt compares casualty rates and the nature of combat from the 17th through 19th centuries, drawing on wars involving Frederick the Great, Marlborough, the Napoleonic campaigns, and the American Civil War. He explores how better weapons don’t necessarily reduce casualties, how proximity in battle changed over time, and how untrained troops often suffer disproportionate losses. His perspective is methodical but never dry—it pulses with energy, intellect, and the moral seriousness of someone who views war not just as strategy, but as a crucible of character.
The Letter That Predicted a Charge
Only three years after this letter was written, Roosevelt put theory into action. When war with Spain broke out in 1898, he resigned his federal post and helped form the 1st U.S. Volunteer Cavalry, known forever as the Rough Riders. His leadership in the Battle of San Juan Hill was not a spontaneous act of bravery, it was the result of years of preparation, both mental and physical.
Roosevelt had studied how morale holds or collapses under fire. He understood when to advance and when to dig in. At San Juan Hill, those ideas became orders, and those orders made history. He led from the front, through bullets and barbed wire, not just as a brave man, but as one who had already anticipated what courage would require.
This letter reads, in hindsight, like a precursor to Roosevelt’s transformation from intellectual to warrior. The clarity of his thinking and the structure of his ideas laid the groundwork for the very battle that would define his public identity and propel him into national politics.
Eight Quotes That Reveal the Mind of Roosevelt
Throughout the letter, Roosevelt offers moments of profound insight—lines that elevate this document far beyond routine correspondence. Here are eight standout quotes, each revealing a different facet of his intellect, strategic thinking, and emerging philosophy of leadership.
1. On Relentless Discipline in War
“The exception was in the wars of Frederick the Great, for he had a wonderfully trained army, and usually fought against superior numbers; and whether he won or lost, he spent his last man and last cartridge.”
Roosevelt praises the value of relentless discipline and determination, characteristics he would come to embody with the Rough Riders.
2. On the Sheer Brutality of the Civil War
“Gettysburg, Shiloh, Gaines Mill, The Wilderness, Franklin, and Cold Harbor were among the bloodiest of our battles; and each one was far bloodier than any battle of the Franco-Prussian War.”
Roosevelt’s statistical comparison between the American Civil War and European conflicts underscores just how devastating the U.S. experience was.
3. On Modern Weapons and Greater Lethality
“A hundred men with breech-loaders pitted against another hundred with breech-loaders fight just as obstinately now as in the days of muzzle-loaders; and on the whole will in a shorter time kill a greater number of one another.”
He dispels the idea that better weapons bring less bloodshed, emphasizing that human behavior remains constant regardless of technological progress.
4. On the Desperation of Doomed Forces
“The beaten side knew they had nothing but death ahead of them, and they therefore fought to the last gasp, killing a goodly number of their foes, and themselves being butchered to the man.”
A haunting reflection on the psychology of resistance, showing Roosevelt’s deep empathy for both sides of a desperate struggle.
5. On Changing Battlefield Distances
“In the old days when a battle ended the victors were separated by but a few hundred feet from the vanquished, and were right in among them as they fled. Now the line that gives way may be a mile distant from the triumphant foe.”
Here he captures how the physical realities of warfare changed as weapon ranges increased, altering outcomes and the aftermath of combat.
6. On the Psychology of Momentum
“There are plenty of regiments which will charge and take and hold a position under tremendous excitement in spite of a loss, which if suffered in a steady, monotonous hammer, hammer, throughout the day, would weary and dispirit them.”
Roosevelt offers a brilliant insight into how morale and adrenaline influence outcomes, foreshadowing the style of leadership he would bring in combat.
7. On Historical Accuracy and Trustworthy Data
“Of course we haven’t very accurate statistics of losses, or at least very trustworthy statistics, prior to the last three centuries or so.”
He shows himself as a careful historian, not only citing facts, but acknowledging the limitations of the historical record.
8. On Hunting, War, and Technological Excess
“Moltke’s battles can last as long as Frederick the Great; as long as Cromwell’s. In game hunting the improvement in rifles has been adopted by an increase in the number of cartridges used per head of game shot.”
In a thoughtful handwritten postscript, Roosevelt draws a clever parallel between war and hunting: technology often leads not to restraint, but to waste.
The Roots of the Roosevelt Presidency
Roosevelt’s charge up San Juan Hill made him a national hero, setting the stage for his election as Governor of New York, then Vice President, and—after the assassination of William McKinley—President of the United States. The philosophies expressed in this letter, however, did not remain confined to the battlefield. They shaped the very foundation of his presidency.
As President, Roosevelt modernized the U.S. military, expanded the Navy, and redefined American power abroad. His foreign policy, anchored in readiness and restraint, was guided by the belief that a nation must be strong not to seek war, but to avoid it. He applied the same values of discipline, strength, and leadership he admired in military history to public administration, conservation, and diplomacy.
This 1895 letter reveals the mind behind those actions. It is a document of thought before power, a private signal of the public leader to come.
A Legacy in Formation
What makes this letter so remarkable is not just its content, but the clarity of vision it reveals at a pivotal moment in Theodore Roosevelt’s life. Written before he wore a uniform or held the presidency, it captures a mind already operating at the level of a seasoned strategist and statesman. With sweeping command of global military history, Roosevelt dissects the causes and consequences of warfare with the precision of a scholar and the urgency of someone preparing for his own test in the field.
In these pages, we see the full formation of the Roosevelt who would charge San Juan Hill, reshape the modern presidency, and redefine American power on the world stage.
This is not a retrospective reflection from an older man looking back, it is the raw, brilliant thinking of a leader coming into focus in real time. For collectors, scholars, and institutions alike, this letter offers something rare: an unfiltered view into the making of Theodore Roosevelt.
Read the Full Letter Here: *Transcribed Below*
“Dear West:
1. The tendency has been to have the losses grow less as the improvement in arms has gone on; but the progress has been broken and interrupted, and often has even been reversed. On our continent, for instance, the losses in the Civil War were relatively very much heavier than in the Mexican War, or the War of 1812; and in these two wars they were relatively heavier on the whole than in the Revolutionary War, or in the old French wars. This may be partially explained, however, by the fact that in all the earlier wars, exactly as in the first year of the Civil War, the fighting was by bodies of ill trained men, who would not stand punishment as better trained troops will.
Moreover, the disproportion of loss has, I think, chiefly decreased on the defeated side. In the old days when a battle ended the victors were separated by but a few hundred feet from the vanquished, and were right in among them as they fled. Now the line that gives way may be a mile distant from the triumphant foe. Of course we haven’t very accurate statistics of losses, or at least very trustworthy statistics, prior to the last three centuries or so. In the Thirty Years’ War, and in the wars between the Spaniards and the Dutch, assisted by English and Scotch mercenaries, and volunteers, in the Netherlands, the defeated were butchered with merciless ferocity, so that their armies were often almost destroyed; but the losses of the victors were not usually great. In the case of the victorious Spanish armies it is astonishing how small they were. In fighting against the Turks, or other barbarous peoples, in the seventeenth and eighteenth centuries the losses were very great, for precisely the same reason that they have often been great in our Indian battles or in a fight between Englishmen and Zulus. The beaten side knew they had nothing but death ahead of them, and they therefore fought to the last gasp, killing a goodly number of their foes, and themselves being butchered to the man. In civilized warfare the change (?) was slow until after the beginning of the present century. In Marlborough’s campaigns, as far as I can find out, the losses were no more heavy than in Wellington’s, and indeed perhaps hardly as heavy. Most of the eighteenth century fighting was not particularly deadly. The exception was in the wars of Frederick the Great, for he had a wonderfully trained army, and usually fought against superior numbers; and whether he won or lost, he spent his last man and last cartridge. The flint lock was used up to the close of the Napoleonic campaigns.
In our Civil war we used percussion caps. The losses were just about as heavy after the first year, as those in Wellington’s Peninsular campaigns. ———— In the Turko-Russian war, while many of the battles were won with very little loss indeed, there was fighting, both at Plevna and at Shipka Pass, in which the slaughter was terrific; but this was largely for the reasons given above, where fighting with savage nations. The fighting in our Civil War was much more bloody than the fighting in the Franco-Prussian War, which took place in the following decade; but on the other hand, it was also much more bloody than the fighting in the Franco-Austrian and Crimean wars and the wars of the Indian Mutiny, which took place in the decade previous.
2. Gettysburg, Shiloh, Gaines Mill, The Wilderness, Franklin, and Cold Harbor were among the bloodiest of our battles; and each one was far bloodier than any battle of the Franco-Prussian War, or than any battle of the Turko-Russian War, save those in which the Bashi-Bazoules got in the wake of the retreating Russians and butchered the fugitives and the wounded. In the Civil War there were over 120 regiments, Northern and Southern, each one of which in some one battle suffered a greater proportionate loss than any regiment in any battle of the Crimean War or than in any battle of the Franco-Prussian War. The heaviest percentage of killed and wounded in any of our regiments was 82 per cent. The heaviest percentage in killed and wounded among the French and English in any regiment in the Crimean War was 49 per cent; and this was also the heaviest percentage in any German regiment in any single battle of the Franco-Prussian War.
3. It is hard to say exactly what allowance to make for the difference of length of time during which slaughter takes place. Often to concentrate slaughter in a few minutes instead of a few hours will break a regiment. On the other hand, there are plenty of regiments which will charge and take and hold a position under tremendous excitement in spite of a loss, which if suffered in a steady, monotonous hammer, hammer, throughout the day, would weary and dispirit them. I think the chief reason for the decrease in loss of recent years has been the fact that with the growing increase in accuracy of the weapons there was less temptation to push a hopeless charge home, and the defeated side was able quicker to realize that its chance was gone. A hundred men with breech-loaders pitted against another hundred with breech-loaders fight just as obstinately now as in the days of muzzle-loaders; and on the whole will in a shorter time kill a greater number of one another.
Is this about what you wish?
Faithfully yours,
Theodore Roosevelt
The time during which a battle lasts has not increased with the improvement in weapons. Moltke’s battles can last as long as Frederick the Great; as long as Cromwell’s. In game hunting the improvement in rifles has been adopted by an increase in the number of cartridges used per head of game shot.”