Mytour wishes you a joyful Fourth of July! In honor of this special day, we present an intriguing presidential list. Theodore Roosevelt (TR) is undeniably one of history’s most captivating figures. His life has been extensively documented, with David McCullough noting in his book “Mornings on Horseback” that the sheer volume of published works about TR is staggering. While much has been written about him, some tragic aspects of his life have been overshadowed by his heroic image. Here, we delve into ten poignant moments from TR’s life.
10. His Son-in-Law Opposed His 1912 Presidential Campaign

After serving two terms, TR entrusted the presidency to his former vice president, Howard H. Taft. However, Roosevelt soon grew disillusioned with Taft, who failed to meet his expectations. Taft’s reluctance to confront conflicts and his alignment with big business disappointed TR. This, combined with Woodrow Wilson’s nomination by the Democratic Party, led TR to run for a third term in 1912.
Although many Republicans backed TR’s campaign—he even outperformed Taft in the election—some opposed his bid for a third term, including his son-in-law, Congressman Nicolas Longworth of Ohio. While TR understood Longworth’s political stance, his daughter Alice remained fiercely loyal to her father, causing tension in her already troubled marriage due to Longworth’s infidelity.
9. His Sister Suffered from a Spinal Deformity

TR’s oldest sister, Anna, known as Bamie, was the cornerstone of the family. Described as an “old soul,” she displayed maturity from a very young age. TR often regarded her as an adult, even during her childhood. Many believed she was the most intelligent in the family, and some speculated that had she been male, she might have risen to the presidency.
Unfortunately, Bamie faced numerous physical challenges and was considered unattractive. She was born with Pott’s disease, a form of tuberculosis that caused a spinal curvature, often referred to as a “hunchback.” Enduring painful braces and grueling treatments, she was deeply cherished by her father. TR held her in high regard and entrusted her with the care of his first daughter for two years. Despite dedicating much of her life to TR and his family, she eventually married later in life and had a son.
8. He Was Frail and Nearsighted in His Childhood

TR’s image as a strong and fearless leader is deeply ingrained in American memory. However, this reputation was hard-earned. In his early years, it was uncertain whether young Teddy would survive into adulthood, much less lead such a vigorous life. At a time when asthma was poorly understood, TR endured frequent and severe attacks. His health was so fragile that family plans often revolved around his condition, as he also battled recurring colds, headaches, stomachaches, and nightmares.
To address his frailty, TR’s father converted a section of their Oyster Bay estate into a gym. Determined to improve his health, TR channeled his relentless determination into physical fitness, growing stronger with age. When doctors warned him after Harvard that his weak heart necessitated a quiet life, TR defied their advice in characteristic fashion by scaling the Matterhorn.
7. His Father Hired a Substitute for Civil War Duty

TR deeply revered his father, Theodore Sr., describing him as “the finest man I ever knew.” However, Theodore Sr. avoided military service during the Civil War by paying for a substitute, a common practice among the wealthy. His decision was influenced by his wife, who was born in the South and had relatives fighting for the Confederacy. Despite this, Theodore Sr. contributed significantly to the Union cause, establishing a program to ensure soldiers sent part of their earnings home to their families, preventing wasteful spending on vices.
Many believe TR felt compelled to restore his family’s honor, which drove him to organize a cavalry unit for the Spanish-American War later in life. His bravery during the Battle of San Juan Hill earned him widespread acclaim. Although he was initially recommended for the Medal of Honor, bureaucratic obstacles delayed the recognition until it was awarded posthumously in 2001.
6. He Endured an Assassination Attempt

TR’s resilience was further cemented by his response to an assassination attempt. While preparing to deliver a campaign speech at the Milwaukee Auditorium during his third-party reelection bid, he was shot at close range by a mentally unstable assailant. Fortunately, the 90-minute speech he carried in his coat, along with his thick coat and metal eyeglass case, slowed the bullet. The projectile lodged in his chest without causing severe damage.
TR’s fortitude was evident when he insisted on delivering his speech before seeking medical attention. Addressing the crowd, he calmly stated, “I don’t know if you fully realize that I’ve just been shot.” Despite blood staining his shirt, he spoke for over an hour. Only afterward did he agree to go to the hospital, where doctors concluded that removing the bullet posed greater risks than leaving it in place. TR carried the bullet for the remainder of his life without significant complications.
5. His Son Kermit Took His Own Life

Kermit, TR’s second son, served honorably in World War I alongside his brothers. After the war, he established the Roosevelt Steamship Company. However, Kermit struggled with severe depression and alcoholism. The financial strain of the Great Depression exacerbated his troubles, compounded by his involvement in extramarital affairs.
Kermit’s struggles reached a point where his brother Archie had him briefly institutionalized. When World War II began, Kermit, though physically unfit for combat, secured a commission through his distant cousin, President Franklin Roosevelt. He served in the Aleutians, aiding in the formation of a local militia against Japanese forces. Despite his efforts, Kermit could not overcome his depression and alcohol dependency, ultimately taking his own life in June 1943.
4. The Death of His Son in World War I Devastated Him

TR was an early advocate for U.S. involvement in World War I, even going so far as to label President Woodrow Wilson a coward for delaying entry on the side of Britain and France. He passionately campaigned for the war and, when it began, volunteered to raise two divisions of soldiers. However, Wilson rejected his offer.
TR took immense pride in his sons’ decision to enlist during the war. However, the death of his youngest son, Quentin, who was shot down over France, left him heartbroken. Overwhelmed with guilt for championing a war that claimed his son’s life, his health began to decline. He often visited the stables, gazing at the horses Quentin adored, repeatedly murmuring, “Oh Quenty-quee, oh Quenty-quee…” TR never recovered from the loss and passed away six months later.
3. He Abandoned a Man to Die in the Amazon Jungle

During the River of Doubt expedition, a crewmember named Julio committed murder. TR insisted to the Brazilian expedition leader that the killer must be hunted down and executed. However, he was informed that Brazilian law required a trial. TR reportedly responded, “In my country, a killer must be killed.” Despite his demands, the expedition continued without locating the murderer.
After committing the murder, Julio fled into the dense jungle, abandoning his rifle in the undergrowth. The expedition members feared he might return to their camp at night to steal or harm them. Three days later, as they canoed down the river, they spotted Julio on the riverbank, pleading to be taken aboard. The Brazilian leader informed him they could not stop and advised him to wait for TR. The following canoes, including the one carrying TR and his son Kermit, passed him in silence. TR later reflected, “That murderer must have been in a living hell.”
2. He Contemplated Suicide

In December 1913, TR and his son Kermit set out on an expedition into the Amazon jungle. They disappeared from the outside world until mid-April 1914. Their journey, which began at the headwaters of the “River of Doubt” and followed its course for 470 miles until it joined an Amazon tributary, was so extraordinary that American geographers and the press initially doubted its authenticity.
During the grueling expedition, TR fell gravely ill, becoming a burden to his team. As a hunter and soldier, he believed no individual should jeopardize the lives of others during such endeavors. When he suggested to Kermit that he be left behind, his son adamantly refused. Recognizing Kermit’s determination and knowing his son would carry his body if he took his own life, TR persevered and completed the journey. His achievement was officially recognized in 1927, and the river was renamed “Rio Roosevelt.” However, the ordeal took a severe toll on his health, and he never fully regained his physical strength.
1. He Never Spoke to His Daughter About Her Mother

Just two days after the birth of their daughter, Alice Lee, TR’s wife Alice passed away due to kidney failure caused by Bright’s disease, which had gone unnoticed during her pregnancy. On the same day, TR’s mother succumbed to typhoid fever. Devastated by the loss of his beloved wife, TR marked the date in his diary with a large X and wrote, “The light has gone out of my life forever.”
Alice Lee was cared for by TR’s sister Bamie until she turned three, after which she joined her father and his new wife. Tragically, TR could never bring himself to speak about Alice’s mother, erasing her memory by tearing out diary pages and burning their correspondence. This silence likely influenced Alice Lee, who grew into a rebellious and flamboyant personality in Washington’s political circles.
