Theodore Roosevelt’s Personal WWI Letters Give A Glimpse Into His Deep Grief

As president, Roosevelt made an indelible mark on history – many still consider him to be one of the best commanders-in-chief that the country has ever seen. Much of that had to do with his heavy focus on character. Roosevelt made the president the center of the American political system and inspired citizens to vote for someone honorable to take the role.

Roosevelt led a notable life outside of office, too. His first wife, Alice, passed away in 1884, just after giving birth to their daughter of the same name. Roosevelt eventually remarried his childhood neighbor and friend Edith Carow – who helped him raise young Alice. Then, the couple had five more children of their own: Ethel, Theodore, Kermit, Quentin and Archibald.

By the time the U.S. had entered into WWI in 1917, Roosevelt’s sons had reached the age at which they could enlist in the military. And all four of them signed up – Theodore, Kermit and Archibald in the Army, and Quentin in the Air Corps. Meanwhile, their father praised their decision to fight in a military operation that he openly supported.

Quentin had no trouble earning the respect of his fellow fighters, and he made a point not to lead with his famous surname while in the trenches. All the while, he kept in touch with his father at home through letters that the two exchanged. Roosevelt’s most heartbreaking message didn’t end up in his son’s mailbox, though.

We’ll learn more about Quentin and his father’s letter later, but let’s first find out about the 26th President of the United States himself. Theodore Roosevelt’s childhood set the tone for the rest of his life. He dealt with a slew of health issues, including asthma so bad that he felt he was being smothered. But he approached his condition with bravery – growing into a child who was equal parts energetic and inquisitive about everything around him.

From there, Roosevelt’s gathered knowledge and an enthusiastic personality helped land him a place at Harvard College. But a place at such a prestigious university didn’t push him into a political career right away. Instead, he penned a book, The Naval War of 1812, which established him as a prominent historian.

For a while, it seemed Roosevelt’s life might push him permanently from the spotlight shone on him because of his well-liked writing. And at first, things went relatively well for him – he and socialite Alice Hathaway Lee exchanged vows in 1880. Two years later, the historian decided to swap his studies for a foray into politics.

First, Roosevelt became a member of the New York State Assembly in 1882. His main focus was tackling corporate corruption, and he made an impression in doing so. But his involvement in the 1884 presidential election could have cost him his entire political career. Roosevelt didn’t run in that year’s race, but he had strong feelings about who should.

Namely, James G. Blaine won the Republican party nomination – a decision that Roosevelt didn’t support. He went so far as to say that he’d vote for a well-appointed Democratic nominee, and this alienated him from many members of the GOP. As such, he decided to retire from his political career that year and ditched the East Coast for North Dakota.

The year 1884 marked two more huge losses for Roosevelt, and they both came on the same day. On February 12 of that year, Alice gave birth to the couple’s first child, a daughter also named Alice. Two days later, though, doctors realized that the new mom’s kidneys had begun to fail – a condition that they hadn’t detect sooner because she had been pregnant.

On the day doctors discovered Alice’s condition, she passed away at just 22 years of age. Making the devastating day even worse, Roosevelt’s mother had died from typhoid mere hours before Alice lost her life. In his diary on February 14, 1884, he reportedly drew a giant X over the page and wrote, “The light has gone out of my life.”

However, losing such important figures in his life did provide a new motivation for Roosevelt to focus on work: namely his political career. He wanted legislators to look further into government corruption in New York City, especially because a new bill could have placed more power in the mayor’s hands. Interestingly, Roosevelt would then become a nominee for that very office in 1886.

Roosevelt didn’t win his bid for NYC’s mayor’s office, but he didn’t expect to win the race against a candidate from the United Labor Party, Henry George. The historian also didn’t expect to find love again in the same year as the election – he married his childhood neighbour and friend Edith Kermit Carow in that year, too.

Some experts believe that Carow and Roosevelt had a relationship while they were teenagers, but it fizzled when he left NYC for Harvard. Once on campus, he had met Alice, thus ending the possible romance with Carow. But the young lovers found their way back together in the wake of his tragic loss – a reconnection so quick that Roosevelt felt a bit nervous to marry someone else.

In spite of those initial fears, Roosevelt and Carow built a robust life together after they wed. Over a ten-year period from 1887, the pair welcomed five children into the world. The eldest they named Theodore, then came Kermit, Ethel, Archibald, and, finally, Quentin. The couple also raised Roosevelt’s daughter from his first marriage. But years later, Roosevelt would suffer further tragedy. His correspondence with his youngest son was cut cruelly short by Quentin’s untimely death.

Of course, Roosevelt’s political star was on the rise as his family grew. He became the Assistant Secretary of the Navy first, but he stepped down from that position to fight in the Spanish-American War. It might’ve seemed that he made the wrong choice to leave politics behind at that point, but Roosevelt’s time spent battling for a U.S. victory made him a national hero.

Roosevelt returned to New York and found the perfect transitional role back into politics. The Republican Party asked him to run for governor of the city in 1898, and he won the election by a mere margin of one percent. And such a prominent political position taught him the lessons he needed. Namely, he learned about the country’s economic issues, as well as political techniques for solving such problems.

Within a year of becoming New York’s governor, Roosevelt had another offer on his plate. The Republicans wanted him to join up with President William McKinley and run as the candidate’s vice president. However, Roosevelt turned down the offer – he didn’t want to take on such a ceremonial role.

But Roosevelt attended the Republican National Convention in 1900, and his position had changed ever so slightly. He made a promise that he’d serve as the party’s vice presidential nominee if the convention chose him to take it. Otherwise, he decided he’d move back to New York and run for governor once again.

But the Republicans wanted Roosevelt on their ticket, and his addition helped McKinley to win his re-election bid by a larger margin than he had in his first presidential race. The joy of victory didn’t last long for the new president, though. Just six months into his second term, McKinley was shot while attending an exposition in New York City.

At first, it seemed as though McKinley would make a full recovery. As a result, Roosevelt, who was on vacation at the time of the attempted assassination, resumed his travels. However, the president’s condition took a turn for the worse – prompting his vice to go to Buffalo to be by his side.

McKinley passed away eight days after the shooting, which meant that Roosevelt had been promoted from vice president to president. He still stands as the youngest-ever person to become commander-in-chief. Indeed, Roosevelt was just 42 years old when he stepped into the most powerful seat in the nation.

Roosevelt’s main focuses centered around his so-called “Square Deal” domestic agenda. He required food companies to adhere to health codes, broke down trusts and began regulating the nation’s railroads. Much of his legacy remains the fact that he conserved and protected many of the country’s national parks and forests. On top of that, Roosevelt ordered the construction of the Panama Canal, and he earned a Nobel Peace Prize for brokering peace at the conclusion of the Russo-Japanese War.

Through it all, Roosevelt made a point to make the role of president into something more prominent. He also made the position become the true figurehead and focal point of the federal government. Furthermore, Roosevelt brought about the idea that political leaders should have good character as well as good policies.

At home, Roosevelt instilled strong character into his children, too, and he expected big things from them. This applied even to his youngest son, Quentin, who grew up much like his father had. The little one had also dealt with health issues early on, but he had a mischievous streak in him as well.

In one anecdote, Quentin sounds a lot like his animal-loving father. In Eric Burns’s book, The Golden Lad, he described how the youngest first child walked into one of Roosevelt’s meetings with a snake slithering on his body. The president sent him out of the office, but told his son to go entertain congressmen waiting for a one-on-one with him.

Author Burns has argued that Quentin was Roosevelt’s favorite of his six children. Regardless of his rank, he did indeed have a strong bond with his dad – they partook in activities both silly and sentimental. Sometimes, they waged pillow fights against each other, and they wrote sentimental letters to one another when they were apart, too.

Time would then take Quentin to study at Harvard before the onset of World War I. The youngest Roosevelt had long wanted to become a pilot, so he joined the U.S. Air Corps to battle from the skies. His father felt extreme pride in Quentin and his three other sons, who had joined the U.S. Army to fight in the war.

True to form, Quentin wrote letters home to share the details of his experience with the U.S. Air Corps. At first, things moved slowly – and the president’s youngest son didn’t like waiting around for his chance to fight. For one thing, he felt he owed it to the family name to go into battle. In one letter to his mother, he wrote, “I owe it to the family – to father, and especially to Arch and Ted who are out there already and facing the dangers of it.”

And, much in Roosevelt’s spirit of fairness and character, his son Quentin turned down opportunities that would have him partaking in the war effort, just not in the dangerous part of it. Instead, he awaited his chance for a front lines placement, and by the end of June 1918 he finally got the chance.

Upon learning the news, Quentin wrote home, “I am now a member of the 95th Aero Squadron, 1st Pursuit Group. I’m on the front – cheers, oh cheers – and I’m very happy.” By July 11 of that year, he had seen his “first real excitement on the front,” he wrote in a letter. The newly minted airman had shot down a German plane on that day.

Tragically, Quentin’s victory over the enemy would be a short-lived one. Just three days after taking down an enemy plane, German fighters trapped him and he was shot twice in the head. Then, the airman’s plane crashed to the ground behind enemy lines. And, soon enough, the world found out that the former president’s son had perished in battle.

Condolences came to the Roosevelts from all over the world, both from prominent international leaders and complete strangers. The former president didn’t have the words to reply at length to most of the bereavement messages, but one letter touched both him and Alice profoundly.

Roosevelt penned a personal, lengthy response to a woman named H.L. Freeland, completing his letter on the one-month anniversary of Quentin’s death. He began by stating how much the message had meant to both him and Alice, but his wife felt unable to write a reply. Nevertheless, he wanted to respond to Freeland because, as he wrote “[her letters] have so singular a quality that I do not mind writing you of the intimate things which one cannot speak of to strangers.”

Roosevelt continued his heartbreaking response to Freeland, and he explained Alice’s grief by simply stating that “Quentin was her baby.” The former president then revealed that “on the night before he sailed, a year ago, [Alice] did as she always had done and went upstairs to tuck him into bed – the huge, laughing, gentle-hearted boy.”

Crushingly, Roosevelt then told Freeland that he and Alice had received letters from Quentin that he had written before his death. The loss of his son’s life proved all the more difficult to swallow because Quentin had “written with real joy in the ‘great adventure’” of life on the front lines – a life that would kill him shortly after penning his letters.

Roosevelt went on to describe how other members of his family grieved Quentin. He wrote, “He was engaged to a very beautiful girl, of very fine and high character. It is heartbreaking for her, as well as for his mother. But they have both said that they would rather have him never come back than never have gone.”

Roosevelt concluded his tribute to Quentin by writing that his son “had his crowded hour, he died at the crest of life, in the glory of the dawn.” He then asked Freeland if her husband had fought in the war, too. Then, he invited the stranger to visit the Roosevelt family abode in New York. And with that, he signed off his message, “Faithfully yours, Theodore Roosevelt.”

Losing Quentin proved a loss that Roosevelt could not get over. His health had already fallen into decline, and he seemed to stop fighting after the death of his youngest son. As Burns put it, “For Quentin’s death was not just another loss – it was the loss.” The letter to Freeland shows the depth of his grief, as does the fact he died a mere six months after losing his youngest son.