Theodore Roosevelt: From Assistant Secretary to President
Early Career and Political Ambitions
Assistant Secretary of the Navy: In , William McKinley, a Republican from Ohio, was elected president. Theodore Roosevelt, deeply interested in the sea and sea power since boyhood, lobbied McKinley extensively for the federal post of Assistant Secretary of the Navy.
McKinley's Reservations: President McKinley, described as an "amiable, cautious conservative," was privately concerned that Roosevelt was “too pugnacious” and frequently engaged in conflicts.
Boss Platt's Influence: McKinley consulted Boss Platt, a powerful political figure, who expressed delight at the prospect of the "young troublemaker" returning to Washington, signaling his desire to remove Roosevelt from New York state politics.
Naval Preparedness Obsession:
"The Naval War of Eighteen Twelve": Roosevelt's first published book concluded that the United States nearly lost the War of due to an unprepared navy, leading to a prolonged and more difficult conflict.
Mission as Assistant Secretary: This obsession drove Roosevelt to seek the Assistant Secretary of Navy position in , specifically to prepare the country for the 20th century.
Roosevelt's Complex Personality and Philosophy
"Balanced Craziness": Roosevelt was characterized as "slightly crazy" but possessing a "very balanced kind of craziness" that kept his "demons in balance" and in "equipoise."
High-Functioning Neurotic: He was highly functional, not suffering from the typical neurasthenia of his era (brooding, headaches) but driven by internal forces and weaknesses he felt compelled to compensate for. He was a "high functioning neurotic."
Need for Validation: He constantly felt the need to demonstrate his masculinity to himself and others.
Quote on Cowardice and War: He famously stated, "Cowardice is the unpardonable" and "No triumph of peace is quite so great as the supreme triumphs of war." He believed the "need for war will vanish" only in the "dim future," which was "ages distant." He asserted that "it is through strife or the readiness for strife that a nation must win greatness."
Social Darwinist Beliefs:
Originating at a time when Darwinism had evolved into Social Darwinism, Roosevelt was a staunch believer in the "survival of the fittest."
"Might Makes Right": This led him to an "unpleasant extent" to believe that "might makes right." He viewed both natural and political nature as "red in tooth and claw," with only the "sentimental flinched from that fact."
Ethical Implications: This "unpleasant dimension" should prompt a retrospective look at Roosevelt "with dry eyes," especially after a century of warfare (the 20th century).
Imperialist Views and the "Large Policy"
Significant Imperialist: Roosevelt is considered "probably the most significant imperialist in American history," despite attempts by apologists to downplay this aspect.
"Most Aggressive Foreign Policy Speech": He delivered a speech to the Naval War College, deemed the "most aggressive foreign policy speech in all of American history," where he declared, "we are going to take our place in the world's arena" as the British Empire showed signs of decline. He proclaimed, "Nature abhors a vacuum. One country and one country only will fill that vacuum, and it must be The United States."
Desire for Expansion: For nearly a decade, he believed no European power should maintain a foothold in the New World. He had previously favored war to seize Canada from Britain.
Cuba and the "Large Policy": When Cubans rebelled against Spanish rule in , Roosevelt immediately advocated U.S. intervention.
"Gentlemen Imperialists": He was part of a secret group in Washington, including his friend Henry Cabot Lodge, who met with Cuban émigrés. They euphemistically called their imperialist agenda the "large policy" and sought to "foment rebellion in Cuba and then have America come to the rescue."
The Spanish-American War: Path to Combat
USS Maine Explosion: On February , the U.S. battleship Maine exploded in Havana Harbor, killing Americans. Although the cause was unclear, Roosevelt blamed Spain and demanded vengeance.
McKinley's Caution: President McKinley, who had witnessed the casualties at Antietam, moved cautiously, stating he wished to "see no more" war. Roosevelt privately disparaged McKinley, accusing him of having the "backbone of a chocolate eclair."
Roosevelt's Decisive Action: Ten days after the Maine incident, while his boss, Secretary of the Navy John D. Long, was away, Roosevelt unilaterally cabled squadron commanders worldwide to be on "high alert" and ordered Commodore George Dewey to prepare to attack the Spanish fleet in the Philippines.
Declaration of War: When McKinley finally requested a declaration of war from Congress in April, Dewey executed Roosevelt's directive, steaming into Manila Harbor and destroying the entire Spanish fleet without losing a single American sailor. Spain, however, still controlled Cuba.
Personal Motivation for War: At years old and a father of six, Roosevelt was determined to fight despite holding an important Washington post. His own father's absence from the Civil War fueled his desire to prove his sense of duty. He expressed this as his "one chance to do something for my country and my one chance to cut my little notch on the stick that stands as a measuring rod in every family." He even claimed he "would have turned from my wife's deathbed to answer that call."
Criticism from Peers: Secretary Long called Roosevelt's desire to fight "foolish" and driven by "vainglory," especially given his wife Edith's severe illness after a difficult childbirth. Friends believed he was "stark, raving, mad."
Roosevelt's Justification: He explained his belief in matching words with action: "I've been out here for a long time saying that we need a war. I have to now deliver myself. I have to show that I can live up to my own standard of honor, and that means that I have to go to war myself."
The Rough Riders: Formation and Deployment
Joining the War Effort: Roosevelt resigned from the Navy Department, had a special uniform made by Brooks Brothers, and ordered a dozen spare pairs of spectacles. He went to war as a Lieutenant Colonel in the First Volunteer Cavalry.
"Teddy's Terrors": Commanded by his friend Colonel Leonard Wood, the unit quickly became known as "Teddy's terrors," "Teddy's cowboy contingent," and ultimately "Roosevelt's rough riders." Their theme song was "There'll be a Hot Time in the Old Town Tonight."
Diverse Recruitment: Roosevelt uniquely assembled a regiment of eager horsemen, primarily from the West (bronco busters, Indians, buffalo hunters, sheriffs, marshals, Texas rangers, cowboys, prospectors), alongside Irish police from New York, Protestant clergymen from New England, fox hunters, yachtsmen, British adventurers, the world's best polo player, and the amateur tennis champion of the United States. He noted, "You would be amused… to see three Knickerbocker clubmen cooking and washing dishes for one of the New Mexico companies."
Historical Expedition: Roosevelt viewed it as a "great historical expedition" and was "thrilled to feel" part of it, believing success would mark "the first great triumph in what will be a world movement."
Defiance of Orders: Desperate to enter battle, when his unit was ordered to wait for a second wave of transports for Cuba from Tampa, Florida, Roosevelt "defied orders, commandeered a ship, and ordered his men aboard." Half of the unit's horses had to be left behind.
Challenging Conditions: The journey and landing were arduous: temperatures above degrees, foul drinking water, inedible tinned beef, and a chaotic landing at Daiquiri (though unopposed by the Spanish). One of Roosevelt's two horses drowned.
Ineffective Command: General William Shafter, the overall commander, weighed over pounds and was debilitated by gout. General Joseph Wheeler, a former Confederate, sometimes mistook the Spanish for Yankees and prioritized his cavalry getting credit over infantry.
Objective: The American target was the port city of Santiago de Cuba, miles away (seven through dense jungle), where U.S. warships had blockaded the harbor.
Combat in Cuba: Las Guasimas, Kettle Hill, and San Juan Hill
Ambush at Las Guasimas: Roosevelt and the Rough Riders, in the lead, were ambushed on a jungle path near Las Guasimas. They fought for hours, driving the Spanish out. Casualties included a dozen killed or mortally wounded and severely or slightly wounded. Roosevelt personally experienced intense fire, with a man killed beside him and a bullet showering him with bark from a tree.
Roosevelt in Battle: This ambush was Roosevelt's "moment of truth." He worried about becoming "overexcited" but steadied himself, demonstrating courage under "withering enemy fire." He marshaled his men, returned fire, and led a charge that flushed out the Spanish.
Advance to Santiago: The Rough Riders, aided by the 1st Cavalry and black troops of the 10th Cavalry, routed the enemy and advanced towards Santiago, where Spanish soldiers were fortified on San Juan Heights and Kettle Hill.
The Assault of July : Roosevelt called this his "crowded hour." The Rough Riders were assigned to support regular troops storming Kettle Hill.
Artillery Exchange and Wounds: The battle began with artillery. Spanish shrapnel bruised Roosevelt's wrist and tore a leg off a man next to him. Bullets sounded "like the ripping of a silk dress."
Leading the Charge: Roosevelt led his men forward under intense Spanish fire as they crossed the San Juan River, with several Rough Riders injured. Finding hundreds of men stalled at the foot of the hill, he mounted his horse, Texas, and led his men forward, challenging a private, "Are you afraid to stand up when I am on horse back?" That private was instantly killed upon standing.
Reckless Bravery: Roosevelt continued up the hill, enduring a bullet nick to his elbow and replacing fallen spectacles while riding. He overcame a wire fence and shot a fleeing Spaniard with his revolver, describing it as doubling him up "neatly as a jackrabbit."
San Juan Heights: From Kettle Hill's summit, he saw the ongoing battle for San Juan Heights and rushed to join it, initially forgetting to give orders to follow (only five men, three of whom were shot down, followed). He then rallied his men and joined black and white American troops to finally drive the enemy from their fortifications.
Post-Battle Reflections: Roosevelt remarked it "had been fun" and a "great day of my life," exclaiming over the "damned Spanish dead." The Rough Riders suffered killed or wounded, which Roosevelt proudly noted was "the heaviest loss suffered by any regiment in the cavalry division." He considered it superior to any hunting trip.
Bloodlust and Desire for Wounds: A friend observed Roosevelt was "reveling in victory and gore." Roosevelt later expressed regret that he hadn't received a "disfiguring and ghastly wound" in the war, highlighting a "bloodlust" and his role as a "killer."
Quest for the Medal of Honor: Roosevelt fiercely lobbied for the Medal of Honor, writing incessant letters to friends like Henry Cabot Lodge. However, the army, disliking his volunteer status and undisciplined approach, resisted granting him the medal.
Critique of Glorification of War: The narrative suggests Roosevelt, despite his glamor, was a "dangerous figure" due to his "glorification of war," which can be an "illusion," as most wars are "prolonged and miserable and wretched with great loss of life."
"The Rough Riders" Book: Published in , his book was rumored to have required printers to order more 'I' type due to his extensive self-narration. A friend, in a mixed compliment, suggested he rename it "Alone in Cuba."
Post-War Political Ascendancy
American Hero: The Spanish-American War, deemed a "splendid little war" by Secretary of State John Hay, transformed Roosevelt into an American hero. Letters urging him to run for Governor of New York arrived even before he sailed home.
Vindication and National Stature: This period "vindicated his father" and launched Roosevelt onto the national scene, making him a hero and opening subsequent political doors.
"Cult of Roosevelt": A "cult of Roosevelt" emerged, fueled by his self-importance and real adoration from people who "worshipped this guy in a cowboy hat," an Easterner turned Westerner who symbolized vitality and strength.
Gubernatorial Bid: Reform-minded New York independents urged him to run on their ticket, but Boss Platt also wanted him as a war hero to strengthen the Republican slate in a difficult election year.
Republican Candidate: Roosevelt rejected the reformers, arguing that "idealism… must be combined with efficiency," achievable only within a major party. He ran as a regular Republican.
Charismatic Campaign: His ten-minute speech in Carthage, New York, was noted more for his "electrical, magnetic" presence than its content, eliciting pleasure and satisfaction from crowds. He "barnstormed" with six uniformed Rough Riders, with bugle calls preceding his speeches. He would shout, "You have heard the bugle that sounded to bring you here… I have heard it tear the tropic dawn at Santiago."
Victory: Roosevelt won, attributing it to "bull luck"—getting into the war, getting out, and getting elected. The Hyde Park Roosevelts, traditionally Democrats, supported him, securing an -vote majority in their town that Democrats previously carried by votes.
Franklin D. Roosevelt's Admiration: A young Franklin, "thrilled" by his "noble kinsman's" achievements, ordered gold-rimmed pince-nez glasses exactly like Theodore's, wearing them more often than his other pair.
Governor of New York: Progressive Reforms
Platt's Concerns: Boss Platt feared Roosevelt harbored "altruistic ideas" and was "a little loose on questions affecting the right of a man to run his own business in his own way."
Progressive Agenda: Roosevelt, though promising to consult Platt, believed Republicans could not safely merely negate issues. He advocated for a "new kind of reform, progressive reform," requiring the party to offer "real solutions to real problems."
Government Intervention: Recognizing the unprecedented growth since the Civil War, Roosevelt believed the "old natural laws of the marketplace were no longer adequate." Government, he argued, needed to "step in to tame the market's excesses and maintain necessary order," righting wrongs through "legislation as well as persuasion."
Balancing Act: He aimed to strike a balance between "mob rule and improper corporate influence."
Successes: Despite Platt controlling the legislature, Roosevelt held two daily press briefings to rally public support and passed significant bills within six months: taxing corporations, limiting working hours for women and children, improving sweatshop conditions, and creating or protecting forest preserves in the Catskills and Adirondacks.
National Recognition: Progressive reformers nationwide took notice. William Allen White hailed him as a "presidential probability" for and "the coming American of the twentieth century."
The Vice Presidency
Hobart's Death: On November , Vice President Garrett A. Hobart died, creating an opening for the election.
Roosevelt's Reluctance: Roosevelt was initially against the vice presidency, viewing it as a "purely ceremonial office." He aspired to the presidency and noted no vice president had been elected president since Martin Van Buren in .
Opposition and Support: Mark Hanna, McKinley's adviser, opposed Roosevelt as a "damned cowboy and an uncontrollable madman." However, progressive Republicans and Westerners admired him, and Boss Platt saw it as an opportunity to remove Roosevelt from New York governance once and for all: "Roosevelt might as well stand under Niagara Falls… as to stop his nomination."
Nomination: The delegates nominated Roosevelt on the first ballot, with his own vote being the only one against him. He stated to Bamie, "The thing could not be helped. The vital thing is to reelect president McKinley, and to this, I shall bend all my energies."
Vigorous Campaign: Roosevelt embarked on an extensive campaign, traveling approximately miles, delivering speeches in towns across states. He was seen as a "new species, a new kind of man in a new century," a sophisticated individual beneath his aggressive exterior.
Election Night Foreboding: After McKinley and he won, Roosevelt told a newspaperman, "Please don't… This election tonight means my political death," adding, "of course, gentlemen, this is not for publication."
Prophecy: McKinley's adviser told the president, "Your duty to the country… is to live for the next four years." Another official presciently remarked, "I feel sorry for McKinley. He has a man of destiny behind him."
James Roosevelt's Death: On December , just over a month after Roosevelt was elected VP, Franklin D. Roosevelt's father, James, died at the age of . Franklin comforted his mother, Sarah, who at faced a "long, lonely widowhood."
The Presidency: An Unexpected Ascent
McKinley's Assassination Attempt: On September , an anarchist shot President McKinley in Buffalo. Roosevelt, on a vacation with his family in the Adirondacks, climbing Mount Marcy, was initially assured of McKinley's recovery.
Urgent Recall: Seven days later, a messenger reached him with news that McKinley was dying of gangrene, with "absolutely no hope." Cabinet members urged his immediate return.
Journey to Buffalo: Roosevelt raced down the mountain by buckboard, wearing out two teams of horses, then took a special train, a total of arduous hours to reach Buffalo.
Oath of Office: McKinley had died. On September , at PM, Theodore Roosevelt took the oath of office in a friend's parlor.
Youngest President: At years old, he became the youngest president in American history.
Franklin's Reaction: Franklin D. Roosevelt, at sea returning from Europe, received the news with "terrible shock" but also excitement, seeing "vivid evidence of how far an ambitious Roosevelt might rise."
Roosevelt's Resolve: Theodore Roosevelt accepted his new role pragmatically: "It is a dreadful thing to come into the presidency this way, but it would be a far worse thing to be morbid about it. Here is the task, and I have got to do it to the best of my ability, and that is all there is about it."