A Personal Letter Gives An Inside Look Of Theodore Roosevelt’s Grief After Losing His Son

Theodore Roosevelt was a huge supporter of the United States’ entry into the conflict of World War I. Little did the former president know, but the four-year-long war would result in a devastating loss for his family.

A personal letter sent by Roosevelt to H.L. Freeland, a complete stranger, gives an intimate look into his sorrow.

Theodore Roosevelt Was The 26th President Of The USA

President Theodore Roosevelt
Fotosearch/Getty Images
Fotosearch/Getty Images

The president of the United States from 1901-1909, many believe Theodore Roosevelt was one of the best the country has ever seen. He was a driving force for both the Progressive and anti-trust policies.

But he was much more than a political figurehead. He was also a loving family man.

He Raised Six Children

Portrait Of Theodore Roosevelt And His Family
FPG/Getty Images
FPG/Getty Images

Roosevelt’s first wife, Alice Lee, passed away in 1884, shortly after giving birth to their youngest daughter, Alice. The soon-to-be president wound up remarrying a few years later to a childhood friend and neighbor, Edith Carow.

Together, they raised Alice and had five more children, Ethel, Theodore, Kermit, Quentin, and Archibald.

All Four Sons Fought In World War I

Roosevelt And Sons
Arthur Hewitt/Archive Photos/Getty Images
Arthur Hewitt/Archive Photos/Getty Images

Even though Roosevelt was no longer in office by the time World War I began, he openly supported the United States’ efforts. He was even proud to say all four of his sons signed up to join the military.

While Archibald, Kermit, and Theodore joined the Army, Quentin decided to join the Army Air Corps (later known as the Air Force).

He Exchanged Letters With His Sons

President Theodore Roosevelt
Underwood Archives/Getty Images
Underwood Archives/Getty Images

Roosevelt was proud of his four sons joining in the fight. He even kept in touch with them through letters. Sadly, not all of the letters were to reach Quentin.

While fighting on the front lines, Quentin made it a point to keep his family lineage quiet. His father had an effect on people.

He Was A Sick Child

Colonel Roosevelt On Horse
Smith Collection/Gado/Getty Images
Smith Collection/Gado/Getty Images

Born in 1858, Roosevelt was lucky to make it out of infancy. He was born with a slew of health issues, including debilitating asthma. Even so, Roosevelt never let the illness slow him down.

He was characterized as brave, with a robust cowboy personality that knew no bounds in every aspect of life.

Roosevelt Was Interested In Biology And Nature

President Roosevelt In Yosemite
Burton Holmes/Archive Farms/Getty Images
Burton Holmes/Archive Farms/Getty Images

His energetic and charismatic personality transferred over to education, too. Since he was homeschooled, Roosevelt was keen to get his hands on as much knowledge as possible. As a result, he attended Harvard College gaining a keen interest in biology.

Interestingly, attending the prestigious school did not throw Roosevelt into a political career right away. Instead, he was an accomplished naturalist and historian who published the book The Naval War of 1812.

Harvard Wasn’t For Him

Theodore Roosevelt
Topical Press Agency/Getty Images
Topical Press Agency/Getty Images

Roosevelt did not even necessarily care for Harvard. In his biography, Theodore Roosevelt, writer Henry Pringle states, “Roosevelt, attempting to analyze his college career and weigh the benefits he had received, felt that he had obtained little from Harvard.

“He had been depressed by the formalistic treatment of many subjects, by the rigidity, the attention to minutiae that were important in themselves, but which somehow were never linked up with the whole.”

He Was Going To Be A Historian

New York Governor Theodore Roosevelt
Bettmann/Getty Images
Bettmann/Getty Images

The novel he penned while attending Harvard was well-received. At the time, it seemed as though Roosevelt had a future as a prominent historian. He even married socialite Alice Hathaway Lee in 1880.

Roosevelt’s life was moving along just fine. Then, he decided to do something a bit different with his career.

1882: Roosevelt’s First Year Of Politics

President Theodore Roosevelt Speaking to Onlookers
CORBIS/Corbis via Getty Images
CORBIS/Corbis via Getty Images

Not long after marrying Alice, Roosevelt decided to get into politics. In 1882, he joined the New York State Assembly, mainly dealing with corporate corruption in the state. In his new job, Roosevelt made a huge impact.

His political career almost stopped before it started, though. And it all had to do with the presidential race of 1884.

Lack Of Support Was An Issue

President Teddy Roosevelt
Bettmann/Getty Images
Bettmann/Getty Images

While Roosevelt did not run for president that year, he had a very strong opinion on who should and should not have run. When it came down to it, James G. Blaine won the Republican nomination.

Roosevelt made it very clear that he did not support the decision and would prefer to see a Democrat in the White House.

Roosevelt Was Alienated From The GOP

Theodore Roosevelt
Hulton Archive/Getty Images
Hulton Archive/Getty Images

Needless to say, Roosevelt’s thoughts on the matter didn’t go over well with the Republican Party. Alienating himself from the rest of the GOP, Roosevelt decided to take a break from not only politics but New York in general.

He packed his and his wife’s bags and moved them from New York to North Dakota.

Tragedy Began To Strike

President Theodore Roosevelt at Desk
B.M. Clinedinst/Library of Congress/Corbis/VCG via Getty Images
B.M. Clinedinst/Library of Congress/Corbis/VCG via Getty Images

What was supposed to be a relaxing life in the country turned into anything but. In 1884, Roosevelt experienced a great deal of loss. First, his mother passed away from typhoid. Then, after giving birth to their first daughter, Alice, Roosevelt’s wife, passed away.

While the birth went smoothly, doctors noticed the new mom’s kidneys were failing.

The Light Let Roosevelt’s Life

12-Theodore-Roosevelt-768w
Library of Congress
Library of Congress

A few days after the doctors noticed Alice had kidney failure, the young mom passed away at 22 years old. Roosevelt was heartbroken. Not only did he lose his mother, but he lost his wife only hours later.

Rumor has it that in his diary, Roosevelt marked February 14, 1884, with a giant “X,” penning underneath it, “The light has gone out of my life.”

He Dove Back Into Politics

5aa2caf42e867228008b4594
Library of Congress/Corbis/VCG via Getty Images
Library of Congress/Corbis/VCG via Getty Images

Losing both his mother and wife did not slow Roosevelt down, though. It actually breathed new life into his political career. He wanted to make sure more power was not given to the New York Mayor, hypothetically resulting in less corruption throughout the city.

Little did Roosevelt know that he was about to be nominated for that very position in 1886.

Another Woman Came Into The Picture

Teddy Roosevelt holds a baby in his arms in a Family Portrait
Buyenlarge/Getty Images
Buyenlarge/Getty Images

That year was a whirlwind for Roosevelt. While he did not win his bid for the New York mayor’s office, he did wind up falling in love with an old friend. Edith Kermit Carow was a childhood friend and neighbor.

Many historians believe the two had a relationship growing up but fizzled away when Roosevelt left for Harvard.

Many More Children Came Into The Picture

GettyImages-640490649
Library of Congress/Corbis/VCG via Getty Images
Library of Congress/Corbis/VCG via Getty Images

Even though Roosevelt was a bit nervous to start a new relationship so quickly, everything worked about between him and Edith. Over the next ten years, the two had five children together.

Sadly, Roosevelt was about to experience some more family tragedy in the years to come when his youngest son, Quentin, fell during World War I.

Roosevelt Became The Assistant Secretary Of The Navy

Theodore Roosevelt Seated on Horse
George Rinhart/Corbis via Getty Images
George Rinhart/Corbis via Getty Images

Not knowing the war was going to be the cause of one of the greatest sorrows in his life, Roosevelt made sure his political career was ground in the military. First, he became the Assistant Secretary of the Navy.

He stepped down from the position to fight alongside his fellow countrymen in the Spanish-American War.

Next, He Fought In The Spanish-American War

Theodore Roosevelt in Uniform
Bettmann/Getty Images
Bettmann/Getty Images

Many people think he made a mistake in his political career by stepping down from the Assistant Secretary position. But after he helped the United States win the Spanish-American War, he was considered a national hero.

After returning from war, it was not long before he found himself back in New York politics.

The Republican Party Asked Him To Run For Governor

Speech of President Theodore Roosevelt for the military preparation
Photo12/Universal Images Group via Getty Images
Photo12/Universal Images Group via Getty Images

In 1898, Roosevelt and his family were back in New York and, that year, the Republican Party asked the war hero to run for governor. It was the perfect move back into politics, so Roosevelt happily ran.

He wound up winning by a slim margin. But, he won the race nonetheless.

Vice Presidency Wasn’t Far Behind

Speech of President Theodore Roosevelt
Photo12/Universal Images Group via Getty Images
Photo12/Universal Images Group via Getty Images

Becoming governor was educational for Roosevelt, as he learned about the numerous issues in the country, including the economic strain and ways to ultimately fix it.

It only took about a year for the republic Party to come back to Roosevelt with another offer — to run alongside William McKinley as his Vice President.

It Took Some Time To Change His Mind

Theodore Roosevelt, Präsident, USA
ullstein bild via Getty Images
ullstein bild via Getty Images

Initially, Roosevelt turned down the offer. It was too much too soon for someone who was, for all intents and purposes, just starting their political career. A trip to the 1900 Republican National Convention changed his mind, though.

Roosevelt said he’d run alongside McKinley if the majority of men at the convention chose him to be the running partner.

Within Six Months, Roosevelt Went From VP To President

McKinley and Roosevelt Campaign Poster
US National Archives/Getty Images
US National Archives/Getty Images

The Republicans wanted nothing more than for Roosevelt to be on the ticket. As it turned out, the party was on to something. Having Roosevelt’s name on the ticket greatly helped McKinley secure the presidency.

Sadly, McKinley was assassinated in 1901. Within six months, Roosevelt went from the Vice President to President of the United States.

Quentin Followed In His Father’s Footsteps

GettyImages-615231276
CORBIS/Corbis via Getty Images
CORBIS/Corbis via Getty Images

Although he was now POTUS, Roosevelt was still a family man, and was always there for his kids, especially his youngest son, Quentin. Born with health issues and rebellious nature, Quentin followed in his father’s footsteps and attended Harvard.

When America joined World War I, Quentin joined the U.S. Air Corps as a pilot.

Roosevelt’s Son Wanted To Be On The Front Lines

Theodore Roosevelt, Politiker, USA, Präsident
ullstein bild/ullstein bild via Getty Images
ullstein bild/ullstein bild via Getty Images

Roosevelt was extremely proud of Quentin for joining the U.S. Air Corps. They wrote to one another as often as possible. For Quentin, though, things were moving along too slowly.

In one letter, 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.”

He Got His Wish

GettyImages-1307589762
William Vanderson/Fox Photos/Hulton Archive/Getty Images
William Vanderson/Fox Photos/Hulton Archive/Getty Images

Quentin wanted to be on the front lines, and, in June 1918, the youngest Roosevelt finally got his chance.

Hearing the news of his placement, Quentin wrote home, saying, “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.” But it wasn’t going to be a happy ending.

Quentin’s Plane Was Fatally Shot Down

Theodore Roosevelt
Topical Press Agency/Getty Images
Topical Press Agency/Getty Images

At first, Quentin was doing well on the front, shooting down enemy planes and doing his job. A month after arriving at the front, Quentin’s plane was trapped by German pilots, and he was fatally wounded.

Letters arrived at Roosevelt’s home from all over the world, offering the family condolences. But the former president could only bring himself to answer one.

H.L. Freeland Got A Response

President Roosevelt at His White House Desk
Bettmann/Getty Images
Bettmann/Getty Images

A woman named H.L. Freeland sent a letter that touched both Roosevelt and his wife Edith’s hearts. So, he decided to write back. It took a long time for him to pen the letter, finally finishing on the one-month anniversary of Quentin’s death.

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 Began To Explain Their Heartache

Roosevelt Signing Thanksgiving Proclamation
Congress/Corbis/VCG via Getty Images
Congress/Corbis/VCG via Getty Images

Roosevelt explained Edith’s grief, saying, “Quentin was her baby. On the night before he sailed, a year ago, [Edith] did as she always had done and went upstairs to tuck him into bed – the huge, laughing, gentle-hearted boy.”

He explained how Quentin had written to them and how excited he was to begin his adventure on the front line.

Quentin’s Fiance Was Grief-Striken

Theodore Roosevelt
Bettmann/Getty Images
Bettmann/Getty Images

Roosevelt continued in the letter, discussing Quentin and saying, “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 Never Got Over His Son’s Death

Portrait Of Theodore Roosevelt
Smith Collection/Gado/Getty Images
Smith Collection/Gado/Getty Images

The letter concluded, saying, “[Quentin] had his crowded hour, he died at the crest of life, in the glory of the dawn.” He even invited the stranger to his family home in New York while asking if her husband had gone to war, too.

As it would turn out, Quentin’s death is something Roosevelt never truly got over. As author Eric Burns stated in his novel The Golden Land, “For Quentin’s death was not just another loss – it was the loss.”