The Bold Life of the Hero of San Juan Hill

The Bold Life of the Hero of San Juan Hill

Larry Holzwarth - November 10, 2019

Like his famous distant cousin Franklin Delano Roosevelt, Theodore Roosevelt served as both Governor of New York and President of the United States. They also shared the distinction of serving as Assistant Secretaries of the Navy. Both were born of privilege, both believed in government’s role ensuring the common welfare. Theodore, known as Teddy (a moniker he detested) was a vigorous and active man for most of his adult life; an avid hunter and outdoorsman, who worked as a cowboy in the west, served in the Spanish American War, boxed and wrestled as president, and later in life explored the Brazilian wilderness, nearly losing his life in the process.

The Bold Life of the Hero of San Juan Hill
Former president Theodore Roosevelt circa 1912. Wikimedia

In 1882, at the age of just 24, Roosevelt produced a book he researched and wrote while studying law at Columbia University, The Naval War of 1812. It remains a standard reference for the war. He later dropped his study of law, not because it was too difficult but because he found it too often confounded common sense. During his lifetime he produced at least 18 books, some of which remain unpublished, and served as an editor of Outlook Magazine. Along with writing, he read extensively, sometimes several books in a single day, which he retained through an almost photographic memory. But it was an adventure which lured him the most, and his life was filled with them. Here are just a few.

The Bold Life of the Hero of San Juan Hill
Roosevelt and a sister watch from a second-story window as Abraham Lincoln’s funeral procession passes his family home in New York, 1865. New York Historical Society

1. He was a sickly and weak youth, plagued with asthma

Theodore was the second of four children born to Theodore Roosevelt Sr. and his wife Martha, a New York socialite known as Mittie. As a young child, he exhibited an insatiable curiosity, teaching himself the art of taxidermy, guided by the books of his father’s extensive library. He also displayed severe asthma, which limited his physical activities and growth. At the age of six, Theodore witnessed the funeral procession for the murdered Abraham Lincoln from a window of his father’s house. He preferred indoor activities to play with other boys and was largely home-schooled, which further isolated him from others of his age. Small, bookish, and spindly, he was a target for bullies.

Following a family trip to Europe, in which he found the clean air of the Alps beneficial to his asthma and that hiking strengthened both his legs and lungs, he began the practice of daily physical exercise he would follow for the rest of his life. In New York, he asked his father to find a boxing coach to teach him how to defend himself, a request his father was pleased to grant. The home schooling, through hired tutors and his own reading, prepared him for admission to Harvard, which he entered in 1876. While there he continued to box competitively, and added rowing to his physical exertions.

The Bold Life of the Hero of San Juan Hill
Roosevelt as he appeared during his college years in the late 1870s. Wikimedia

2. Roosevelt’s wealth enabled him to choose politics as his career

While Roosevelt was at Harvard his father died, and the young man inherited the equivalent of just over $3 million in today’s money. After graduating with honors he returned to New York, enrolling in Columbia Law School, where he worked on his book on the War of 1812. He also entered politics, attending meetings of the District Republican Association which met at Morton Hall. The meetings and the number of allies he developed among his peers caused him to choose politics as his career. He did not complete his law degree and later described his decision as “I intended to be one of the governing class”. Roosevelt’s New York was dominated by machine politics at the time.

Roosevelt was still in school when he married Alice Lee. Like his father, the young man chose a New York socialite for his bride. In 1884 Alice gave birth to their daughter, Alice Lee Roosevelt, before dying of complications of kidney disease two days later. Earlier that same day, in that same house in an upstairs room, Roosevelt’s mother had died after being stricken with typhoid fever. The devastating double blow drove the young man into depression, he left his daughter in New York in the care of his younger sister. He returned to Albany hoping to bury himself in his work. Though it offered him some distraction from his grief, he never mentioned his wife Alice in his diaries or conversation again, beyond the diary entry, “The light has gone out in my life” on the day she died.

The Bold Life of the Hero of San Juan Hill
Roosevelt’s last diary entry in reference to his wife, Alice. Wikimedia

3. Roosevelt went West to recover from his grief and depression

Following the 1884 Republican National Convention, in which Roosevelt made an impression which was in many ways politically controversial, he announced his retirement from politics and moved to a ranch in North Dakota. For perspective, it should be considered that Custer had been defeated just eight years earlier, and the towns were still very much of the Wild West image. Roosevelt arrived carrying a knife from Tiiffany’s, rifles custom-built and engraved, and in costume presenting him as very much an Eastern dandy. From his ranch at Chimney Butte on the Little Missouri River, he learned the tasks of a cowboy, and he built a second ranch, which he named Elkhorn.

In 1886 Roosevelt was at the ranch when his boat was stolen and quickly vanished down the Little Missouri. Roosevelt and two hired hands hastily put together a raft and set off in pursuit. When they caught the three thieves Roosevelt disarmed them, kept watch over them with his own shotgun, and escorted them to Dickinson, North Dakota, where he learned there was a reward offered. He collected the promised $50 and returned to his ranch. Roosevelt wrote several magazine articles and three books describing his life on the ranch, though he did not remain there year-round, having interests in New York which required his attention.

The Bold Life of the Hero of San Juan Hill
Roosevelt was shattered by the loss of his wife Alice, and went west in part to recover. Library of Congress

4. Theodore experienced the west in an almost stereotypical manner

While Theodore Roosevelt was in the west, particularly along the Little Missouri, he wanted to experience America’s western experience in all of its legendary glory. And so he did. He rode with other ranchers to stop stampeding cattle, amusing the hard-bitten ranchers with his cry of “Hie on quickly there!” as he rode among the herd. Roundups which meant weeks in the saddle by day, and keeping watch in camps by night, were a part of his experience. So were the celebrations in local saloons when the roundups were completed. In one, Roosevelt disarmed a drunken cowboy, in another he engaged in fisticuffs with a local gunfighter, putting his boxing experience and skills to good use.

Though he was officially retired from politics, or so he claimed, he used his political skills to organize the first cattlemen’s association in North Dakota. The formerly frail New York society gentleman transformed himself into a hardened and athletic young man, skilled with rifle and shotgun, as well as on horseback (though he had ridden polo ponies before venturing to the west). He also enjoyed hunting bison, and the tales of the formerly great herds which were then nearly gone sparked his already keen interest in conservationism, which he retained for the rest of his life, dedicated both to hunting and to the well-being of the animals he hunted.

The Bold Life of the Hero of San Juan Hill
Roosevelt, seen here hunting in Colorado, loved the west, though his investments there were mostly failures. Wikimedia

5. Roosevelt predicted the disasters which befell his ranches in 1886-87

In one of the books Roosevelt wrote about life in the Dakotas, Hunting Trips of a Ranchman, he predicted that the boom in the cattle industry in the Badlands region of the Dakotas was doomed to collapse. In his view, there were simply too many cattle being bred for the land to sustain, though he was one of the ranchers participating in the industry. The growing season of 1886 was abbreviated by late spring and early winter, and during the winter cattle died by the thousands, with ranchers possessing inadequate fodder to feed them. Roosevelt was away that winter, traveling in Europe with his new wife, Edith Carow Roosevelt.

When he returned to the United States he learned of the financial disaster which had erased his investments in ranching and cattle, and he began to divest himself of both, though he continued to invest in cattle from the herds of his neighbors. The experiences he had in the Dakotas, and his widely read writings of them, established his reputation as a man of action, possessed of physical and moral courage, dedicated to the well-being of others. He re-entered New York politics rejuvenated, remarried, and determined to advance his political career as a leader of the progressive movement then took hold in American politics.

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Then Governor of New York Theodore Roosevelt, second from left. Wikimedia

6. Roosevelt clashed with the American system of Civil Service sinecures

In 1889 Benjamin Harrison, whom Roosevelt had supported in the election of the preceding year, appointed department store magnate John Wanamaker as Postmaster General of the United States. He also appointed Theodore Roosevelt to the Civil Service Commission. Roosevelt viewed the position as one which gave him the authority to vigorously enforce the Civil Service regulations which were for the most part winked at as part of the political spoils system by both parties. Wanamaker fired thousands of postal employees, replacing them as patronage jobs for supporters of President Harrison. Roosevelt in turn enforced civil service regulations, exposing the patronage, and removing Harrison supporters.

Roosevelt’s actions tarnished the reputation of Wanamaker and eroded support in the public mind for Harrison. When Harrison ran for re-election in 1892 Roosevelt actively campaigned for him, blaming the exploitation of the spoils system on Wanamaker, rather than the president, but Harrison lost to Grover Cleveland. Cleveland retained Roosevelt in his position, though Wanamaker was replaced by Wilson Bissell (Postmaster General was a Presidential Cabinet position at the time). Roosevelt remained on the Civil Service Commission until moving on to a more adventurous job in New York City.

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William “Big Bill” Devery was one of the most corrupt policemen in New York history. New York Daily News

7. He took his position with the New York City Police Commission seriously

In 1894 Roosevelt was approached by leading reformers hoping he would run for Mayor of New York. His wife Edith opposed the idea, and he turned them down. When a Republican candidate prevailed in the election on a platform of reform, Roosevelt realized he had made an error in judgment as regarded his political career. The new mayor, William Lafayette Strong, offered Roosevelt a position on the New York Police Commission, and though Roosevelt had no experience in law enforcement (other than his adventures in North Dakota) he accepted the post. Once again, what was considered by many to be a sinecure was in his hands converted to position of power.

The New York Police Department was, like much of the bureaucracies of the city, rife with corruption throughout. Bribery was common, gambling and houses of prostitution were protected by police officers, as were other criminal activities throughout the city. The corruption rose through the ranks of the department, and Roosevelt decided that where it directly impacted the residents of the city – the police officer on the beat – was where it must be confronted first. Roosevelt set about reforming the police department with a vigor never seen from a commissioner before in New York City.

The Bold Life of the Hero of San Juan Hill
Policing New York City was a challenge presented by crime and a police force corrupt from top to bottom. YouTube

8. William “Big Bill” Devery was an example of a police official who opposed Roosevelt

William Devery was a captain of the New York Police who once berated the men of his precinct, warning them that their collective graft was to stop immediately. “If there is any grafting to be done, I’ll do it”, he told them. “Leave it to me”. He was later convicted of bribery and extortion and fired from the force. He appealed successfully and eventually became New York’s first-ever Chief of Police in 1898. He made so much money through his illicit activities that he became a co-owner of a professional baseball team in Baltimore, moved it to New York, and named it the Highlanders. Today they are known as the Yankees. Devery was representative of what Roosevelt faced when reforming the New York Police Department.

Roosevelt gained the support of the public for a time with his vocal and written denunciations of the unsavory relationship between the police officers on the street and the ward bosses from Tammany Hall. Police precinct captains were the arbiters of criminal activity throughout most of the city, their officers were the enforcers of their decisions. But with the public, and most of the city’s newspapers, supporting Roosevelt the police captains found that they had to lay aside much of their criminal activities until Roosevelt overstepped and lost the goodwill he had built with the public.

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Jacob Riis documented the plight of New York’s poor, often in company with Police Commissioner Roosevelt. Wikimedia

9. Roosevelt became popular with the people through walking the streets of the city

When he learned that many police officers spent their overnight shifts involved in other activities, such as visiting saloons, brothels, or just sleeping, he began to walk the streets at night, armed with a stick and accompanied by muckraking journalist Jacob Riis. Riis ensured that their nightly strolls were reported in the Evening Sun. Officers encountered in other activities than policing their beat were disciplined, as were their commanders, and the Evening Sun named names. On more than one occasion Roosevelt made arrests himself as part of his walking the beat, holding a miscreant until an officer arrived to take him into custody.

The goodwill generated by Roosevelt’s nocturnal activities kept him popular and promised to boost his political fortunes until he began to enforce the law prohibiting the sale of alcohol on Sundays. At a time when most workers labored six days a week, Sundays were welcomed by saloon owners and patrons. To many, Roosevelt became less of a reformer and instead more of a zealot. The attempt to enforce the Sunday liquor laws was unsuccessful, and Roosevelt’s political fortunes once again waned within the Republican party, which considered him too broadly disliked by the public to be supportable in local elections.

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Roosevelt rebuilt and modernized the US Navy, seeing it grow into the world’s third largest. US Navy

10. Appointment as Assistant Secretary of the Navy put Roosevelt on the national stage

After Roosevelt supported William McKinley in the election of 1896 he was rewarded by the incoming administration with the office of Assistant Secretary of the Navy. Roosevelt became the de facto Secretary of the Navy due to the real Secretary, John D. Long’s, lack of interest in issues. He preferred to focus his attention on appearances and meetings of McKinley’s cabinet. Roosevelt used his position to express his views on global affairs, and most importantly to his own career, the Spanish presence in Cuba. Roosevelt took it upon himself to send orders directly to the commanders of the Naval squadrons around the globe, and following the explosion of USS Maine in Havana Harbor, he prepared the fleets for war.

Roosevelt was among the leading advocates for war with Spain both before and after USS Maine’s destruction. Maine was destroyed in February, 1898, and by April McKinley had lost hope of reaching the diplomatic solution he sought and asked Congress to declare war. Roosevelt anticipated the declaration and ordered the ships in both the Caribbean and the Philippines to prepare to attack Spanish facilities and fleets. He then resigned as Assistant Secretary of the Navy and joined a unit of volunteer cavalry being formed under the command of US Army Colonel Leonard Wood, eager to serve in the war he had worked so hard to bring about.

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Roosevelt first told the story of the Rough Riders in Scribner’s Magazine. Library of Congress

11. The First United States Volunteer Cavalry Regiment

One of Roosevelt’s last acts as Assistant Secretary of the Navy was to ensure the 1st United States Volunteer Cavalry was properly equipped with the most advanced weapons available to the US Army. He also ensured that their uniforms were distinctive. He later wrote in his book The Rough Riders, “They looked exactly as a body of cowboy cavalry should look”. Roosevelt ignored the pleadings of his wife Edith (and political allies in Washington) to remain at his post with the Navy and joined the regiment as it was training in San Antonio, Texas, determined to see action in the War with Spain, which he expected to be short.

Roosevelt called the newly formed unit the Cowboy Regiment, but it was a diverse group which included adventure-minded individualists from across the country. Professional and amateur athletes, prospectors and miners, wealthy men of business, cowboys and lawmen from the west, and men from other walks of life comprised its ranks. They trained in the operations of cavalry, learned to maneuver and deploy into battle on horseback, with Leonard Wood in command of the regiment – comprised of 12 companies – with Roosevelt second. They became known as the Rough Riders, a name borrowed from Buffalo Bill’s popular Wild West Show.

The Bold Life of the Hero of San Juan Hill
Not all of the Rough Riders were sent to Cuba due to a shortage of transport ships. Wikimedia

12. Not all of the Rough Riders were sent to Cuba

When the Rough Riders were assembled in Tampa, Florida, for shipping to Cuba there was insufficient transport available to carry all of the men, their horses, and their equipment. The regiment was already weakened from its original strength through the loss of approximately 25% to disease and accidents. Only eight of the twelve companies arrived in Cuba, and very few of the horses, meaning the men who had trained to move on horseback were relegated to marching, in boots designed for riding rather than walking. They also lacked the means of carrying provisions for more than a few days. They had also not been trained to operate in the thick jungles they encountered.

The Rough Riders saw their first combat during an attack on a Spanish position at Las Guasimas, supported by a regiment of regular cavalry and another regiment of black troops known as buffalo soldiers. They assaulted a steep hill, though according to Roosevelt, “Many of the men, footsore and weary from their march of the preceding day, found the pace up this hill too hard…” Colonel Wood was reported killed (inaccurately) and Roosevelt assumed command, which he later relinquished when Wood was found uninjured following the battle. The Americans were encamped on the battlefield for the following six days, with many being stricken with tropical diseases.

The Bold Life of the Hero of San Juan Hill
Roosevelt (far right) stands to the left of his commanding officer in Cuba, Colonel Leonard Wood, US Army. Wikimedia

13. Roosevelt assumed command of the Rough Riders while in Cuba

The overall commander of the American cavalry in Cuba was Joseph Wheeler, a veteran of the Confederate Army during the Civil War. When he became ill, a shuffling of the senior officers put Wood in command of a brigade, and Roosevelt became a colonel of volunteers and in command of the Rough Riders, who by then were calling themselves “Wood’s Weary Walkers”. After a week of being encamped at Las Guasimas, the regiment was ordered to move forward a distance of about eight miles, near the San Juan heights, and remain in position there until they received further orders.

The Rough Riders moved forward with the rest of the American dismounted cavalry on July 1, 1898. They were to join in an attack which threatened the Spanish-held city of Santiago de Cuba, by taking the heights which overlooked the city. The names of San Juan Hill and nearby Kettle Hill were given to positions occupied by entrenched Spanish troops by the Americans. As the battle opened the Rough Riders had no orders to advance, but they came under artillery fire and Roosevelt, one of the few men on the battlefield who was mounted, sent messengers urging that he be allowed to move his regiment forward in support of the infantry preparing to assault Kettle Hill.

The Bold Life of the Hero of San Juan Hill
Roosevelt and his Rough Riders pose at the top of Kettle Hill in Cuba, 1898. Wikimedia

14. Roosevelt assaulted Kettle Hill against orders

The plan to take Kettle Hill was through a gradual assault, exchanging fire with the enemy above while using natural cover offered by the terrain to slowly approach the crest. The Rough Riders were ordered to hold the position as a covering force at the base of the hill, moving upwards when called from the troops above. Roosevelt disliked the slow pace and when he realized that he was the senior officer present at the base of Kettle Hill, he ordered a full charge up its slope. Gatling guns at the base of the slope covered the charge and suppressed Spanish fire, though casualties were nonetheless heavy during the assault.

The troops advanced in small groups, covering each other, until they reached the crest and captured the Spanish positions. The entire affair took less than twenty minutes, and the rest of the San Juan heights were secured within an hour. Thus, the famed charge-up San Juan Hill by the Rough Riders was in reality an attack on Kettle Hill, using standard infantry tactics, supported by Gatling and machine guns, which also broke up Spanish counterattacks. The naval battle of Santiago and the capture of the heights allowed the United States to capture Santiago de Cuba in a short siege, and the war with Spain was effectively over by the beginning of August. On August 14, the Rough Riders who had served in Cuba were landed at Montauk, New York.

The Bold Life of the Hero of San Juan Hill
Following his Cuban adventures Roosevelt preferred to be addressed as Colonel by all. Library of Congress

15. Roosevelt used his short campaign in Cuba to launch his national political career

When the Rough Riders landed at Montauk they found the four companies which had been left behind in Tampa waiting for them. Their charge was already famous in the United States, as was their commander. Gifts and salutations were received by the regiment, and by Roosevelt, who in speeches and interviews stressed the superb horsemanship of his men, while not directly claiming that they had ridden while in Cuba. “I doubt if there was any regiment in the world which contained so large a number of men able to ride the wildest and most dangerous horses”, he wrote in The Rough Riders, which was published in 1899 and became a best seller.

In mid-September, the regiment was disbanded. It had existed as a military unit for just six months. Roosevelt commanded it for less than three, but after returning to civilian life he preferred to be addressed as Colonel Roosevelt, or simply Colonel. Then known nationally thanks to the effusive coverage of the press regarding his actions in Cuba, he was affectionately known as Teddy, much to his annoyance. He later recalled the day at Kettle Hill as the “great day of my life”. On that day Roosevelt too arrived at the top of the hill on foot, after his horse was unable to negotiate a tangle of barbed wire.

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Roosevelt found his war record a useful subject when campaigning for the rest of his life. Wikimedia

16. Roosevelt was elected governor of New York in 1898

Shortly after returning to the United States from Cuba, Theodore Roosevelt was elected Governor of New York, taking office on New Year’s Day, 1899. He immediately established the practice of meeting with the press twice each working day, ensuring his views were reported to the people. He also pushed for the creation of franchise taxes, with the owners of privately held instruments of public benefits, such as streetcar systems, commuter railroads, and others, required to pay taxes to the state. He argued in his press conferences that an alternative would be for the state to take over all such systems and make them publicly owned, silencing opposition.

New York was at the turn of the twentieth century the most populous of the states, and Roosevelt’s position as Governor of the State, his war record, and his national popularity as Teddy, made him an attractive candidate with Republican Progressives to contest the presidency with McKinley. He did not agree, nor was he attracted to the idea of joining the ticket as a vice-presidential candidate in the election of 1900. As Governor of New York, Roosevelt alienated the Republican machine controlled by Thomas Platt, who began to scheme for a means of ridding himself of the reform-minded Roosevelt.

The Bold Life of the Hero of San Juan Hill
Roosevelt on a campaign stop in Buffalo, 1900. Library of Congress

17. Roosevelt found the vice presidency a powerless position and chafed in it

Although Roosevelt initially announced that he would not accept nomination to serve as McKinley’s running mate in 1900, he was persuaded to accept it after political maneuvering by Platt at the Republican Convention assured he won unanimously. Once he had the nomination in hand he campaigned tirelessly for the Republican ticket. He barnstormed by train, visited 23 states, and made nearly 500 individual appearances. His war record was stressed by the campaign, and he exhibited the vigor of his reputation, spoke with exuberance, and connected with the common man and the middle class as one of them, though in truth he was a man of privilege and wealth.

He took office as Vice President of the United States in March, 1901, with the full knowledge that it was a position of little power and influence. He had taken such positions before, which were little more than sinecures, and had made them influential through the force of his own personality. He tried to do the same in Washington but found that it was impossible due to the definition of office in the Constitution. As vice president, he presided over the Senate, the only prescribed duty of the office, for just a few days. His only other activity was in giving speeches at various events across the country, an activity which bored him until September.

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Roosevelt served as vice president under William McKinley (left) for just six months before ascending to the presidency. Wikimedia

18. Roosevelt ascended to the presidency upon the death of William McKinley

William McKinley was shot on September 6, 1901, in Buffalo, New York. Roosevelt was vacationing in New England, and he went to the president’s bedside, where it was believed that the wound was not mortal. Roosevelt resumed his vacation. McKinley died on September 14 in Buffalo, and Roosevelt took the oath of office in that city the same day, at 42 the youngest man to hold the office of President of the United States in history. He retained most of McKinley’s cabinet, including John Hay as Secretary of State (Hay had been a personal secretary for Abraham Lincoln). Roosevelt then created the modern presidency.

One of his habits as Governor of New York was exhibited in the White House, when he insisted in daily briefings of the press, allowing reporters to submit questions. It was Roosevelt who designated space within the White House for the press, which helped him gain favorable coverage. Roosevelt entered the White House with 6 children, his wife, and personal staff and servants, and found the building too cramped to accommodate the completion of business as well. The West Wing was built to house the offices of the administration, and rebuilt several times by succeeding presidents.

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As president, Roosevelt enjoyed immense popularity with the public and press, and used it to his political advantage. Wikimedia

19. The Roosevelt administration was marked by expansion of presidential power

Roosevelt won election on his own in 1904, and when he left office in 1909 it was left to his hand-picked successor, William Howard Taft. He remained popular throughout his nearly two full terms, and his popularity with voters, and with most of the press, allowed him to significantly increase the power of his office. He used that power to increase the power and international prestige of the United States. He brokered a peace treaty ending the Russo-Japanese War, while at the same time expanding the strength of the United States Navy, until by the end of his presidency it was the third largest in the world. He championed the completion, by the United States, of the Panama Canal after the French failed.

Roosevelt’s use of the office placed the presidency in the center of the American government, more so than had any of his predecessors, a position which it has retained ever since. He made the environment a national concern. He used his office to influence the perception of American manhood, arguing for strenuous exercise and activity as superior to taking one’s ease sedately. He also stressed the moral value of strenuous competition and competitive sports, taking part in both publicly and in private. When he left office he was fifty years of age, and he had no intention of slowing down himself.

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Roosevelt helps to secure a captured crocodile during the Smithsonian-Roosevelt Expedition to Africa. Wikimedia

20. The Smithsonian-Roosevelt African Expedition

Roosevelt left office in March, 1909, and later that same month sailed for Africa as part of a safari intended to obtain specimens for the Smithsonian Institution. The expedition also obtained specimens for the New York-based American Museum of Natural History. It was funded by earnings from Roosevelt’s writings, and by Andrew Carnegie. It was led by Roosevelt, who hired a local hunter-tracker to guide the group on safari, and included staff from the Smithsonian among its permanent members. Roosevelt, who had first learned to hunt big game in the Dakotas when after bison, enjoyed the hunt immensely, despite criticism from some at the time. He defended it as essential to the pursuit of knowledge.

The safari yielded over 11,000 animals which were either trapped or killed, including over 1,000 large animals. Roosevelt or his son Kermit, who was not with the expedition for its entire time, killed between them 512, including 17 lions and 11 elephants. As the safari unfolded animals and skins were shipped to the Smithsonian, preserved in salt, for mounting. Duplicates were loaned to other museums and institutes in the United States. By the time the safari was completed over 23,000 examples of zoological specimens were collected, along with several thousand specimens of plants. Roosevelt followed the safari with a tour of Europe.

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Running for a third term as a third party candidate split the Republicans in 1912 and handed the election to Woodrow Wilson. Wikimedia

21. Roosevelt returned to the United States to run once again for president

In 1910 Roosevelt found himself at odds with many of the policies of his successor, William Howard Taft, and a growing rift within the Republican Party between Progressives and Conservatives. In 1912 Roosevelt first attempted to wrest the Republican nomination for president from Taft; failing in that he announced he would run as a third-party candidate. The Progressive Party was given the nickname of the Bull Moose Party after Roosevelt answered a question about his physical fitness by replying, “I’m as fit as a bull moose”. “To destroy this invisible government, to dissolve the unholy alliance between corrupt business and corrupt government”, was cited by Roosevelt as the goal of his candidacy.

Roosevelt, as he had in 1900 and 1904, campaigned tirelessly. He argued that “every monopoly in the United States opposes the Progressive Party”, implying that the Democratic candidate, Woodrow Wilson, supported the monopolies. Roosevelt argued the government was obligated to act against monopolies and trusts, citing by name in speech after speech the Sugar Trust, the Tobacco Trust, the Steel Trust, and the Standard Oil Trust. His campaign was nearly derailed in October, 1912, when a saloonkeeper shot him in the chest as he was preparing to deliver a speech in Milwaukee, Wisconsin.

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An x-ray of the former president’s chest clearly shows the bullet lodged in muscle. Wikimedia

22. Roosevelt was more severely wounded than he realized

When Roosevelt was wounded in an assassination attempt, he immediately called to his audience that he was alright, and to hold the assassin for the police without harming him. The bullet had penetrated his fifty-page speech, which was folded in his coat pocket, as well as his eyeglasses case before entering his chest. In the absence of coughing blood Roosevelt, who could sense that he was bleeding through his shirt, declined medical assistance and announced to the crowd, “Ladies and gentlemen, I don’t know whether you fully understand that I have just been shot, but it takes more than that to kill a Bull Moose”. He then delivered his speech, titled Progressive Cause Greater Than Any Individual. It took more than 90 minutes.

Following his speech and after acknowledging the applause and congratulations of the audience, Roosevelt submitted to an examination of his wound by doctors. It was found that the bullet, which had lost some of its velocity when it passed through his speech and metal eyeglasses case, had lodged in the muscles of his chest. Removing it was determined to be more dangerous than allowing it to remain where it was, since it had not entered the chest cavity. The bullet was left alone after it was probed, and Roosevelt carried it in his chest for the rest of his life. Three weeks later he easily surpassed the vote total of the incumbent Taft, but lost the election to Woodrow Wilson.

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The Roosevelt Expedition to South America nearly killed the former president. Wikimedia

23. A trip to South America was next for the former president

In 1913 Roosevelt planned to recover from his defeat in the presidential election by conducting a speaking tour in South America, after which he hoped to join a cruise on the Amazon arranged by a friend. Officials within the government of Brazil suggested to Roosevelt that he would enjoy an expedition to explore the River of Doubt, a stream of which the headwaters had been recently discovered, and which had been unknown until then. The thought of an adventurer exploring where no other white man had ever gone was enough for Roosevelt, and he eagerly agreed, gaining sponsorship from the American Natural History Museum in return for the specimens he was able to collect.

Edith was appalled at the idea of the former president, who still carried an assassin’s bullet in his chest, being in the South American jungles for such an extended period. She insisted that their son Kermit accompany the expedition, and the recently engaged Kermit acquiesced to his mother’s demands, postponing his nuptials to accompany his father. Near the end of 1913, the party set out from Caceres on the expedition, led by Candido Rondon, who had discovered the headwaters of the River of Doubt. They reached the headwaters in February, 1914, and part of the expedition turned back, leaving the Roosevelts, Rondon, a representative of the American Museum of Natural History named George Kruck Cherrie, and fifteen Brazilian litter-bearers to travel down the river.

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Former president Roosevelt, still hale and hearty circa 1910. Library of Congress

24. Roosevelt nearly died on the expedition which resulted in the deaths of three men

One Brazilian porter died on the expedition, drowned in rapids encountered. Another was murdered by a porter who was then stranded in the jungle, never to be seen again. All suffered from hunger, and all except Rondon suffered further from malaria and other tropical illnesses. Roosevelt suffered a deep cut on a leg which quickly became infected, and likely would have died had the party not stumbled upon a party of men in the jungle to tap rubber trees, employed by rubber companies which harvested the substance to manufacture tires, newly in demand by the automobile industry.

Roosevelt was severely weakened by his infection and the effects of malaria, and when the group reached Manaus in Brazil he was finally given medical care. He recuperated slowly, and by the time he returned to the United States three weeks later, he was still weak and frail. He could speak only for short periods of time, and the booming voice and vigorous delivery had been reduced to a whisper. He nonetheless arranged several speaking engagements through the National Geographic Society to defend his claimed discoveries when they were challenged by critics who did not believe the expedition had found the river. A subsequent expedition proved that they had.

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Theodore Roosevelt’s funeral in Oyster Bay, New York, January, 1919. Wikimedia

25. Roosevelt never fully recovered his health after the South American Expedition

Roosevelt gradually regained some of his strength following his return to the United States, but he never returned to full health. He had been so ill on the expedition that he contemplated suicide, believing his illness slowed the rest of the expedition to the point that it was a threat to them all. Kermit persuaded him to continue. Though Roosevelt lacked his former vigor, his voice was heard throughout the First World War, highly critical of Wilson. Congress authorized Roosevelt to raise a unit similar to the Rough Riders, and the old warrior was willing, but Wilson announced that such a unit would not be deployed with the American Expeditionary Force, and the idea died on the vine.

In January, 1919, Roosevelt experienced breathing difficulties reminiscent of his asthma attacks as a boy. He summoned a doctor to his Sagamore Hill home, and reported he was feeling much better after receiving treatment. The next morning he was found dead, having died in his sleep at the age of sixty, in the early morning hours of January 6. He was buried at Youngs Memorial Cemetery overlooking Oyster Bay. He has been called the most well-read of any American president other than Thomas Jefferson, though where he found time for reading is hard to imagine.


Where do we find this stuff? Here are our sources:

“TR: The Last Romantic”. Henry W. Brands. 1997

“Mornings on Horseback: The Story of an Extraordinary Family, a Vanished Way of Life, and the Unique Child Who Became Theodore Roosevelt”. David MacCullough. 1981

The Wilderness Warrior: Theodore Roosevelt and the Crusade for America”. Douglas Brinkley. 2009

“Municipal Administration: The New York Police Force”. Theodore Roosevelt, The Atlantic. September, 1897

“Tammany Hall Police Commissioner William ‘Big Bill’ Devery”. Dan Gunderman, New York Daily News. January 8, 2017. Online

“The Rough Riders”. Theodore Roosevelt, 1902

“Governor Theodore Roosevelt”. Article, National Governors Association. Online

“Theodore Roosevelt”. Article, About the Presidents. White House Online

“Teddy Roosevelt’s Epic (But Strangely Altruistic) Hunt for a White Rhino”. Darrin Lunde, April 12, 2016

“The War of 1912”. Patricia O’Toole, TIME Magazine. June 25, 2006

“Who Shot T. R.?” Article, Theodore Roosevelt Birthplace National Historic Site. National Park Service. Online

“Through the Brazilian Wilderness”. Theodore Roosevelt. 1914

“Theodore Roosevelt Dies Suddenly At Oyster Bay Home”. The New York Times, January 7, 1919. Online