Theodore Roosevelt remains one of the most popular men in American history and certainly one of our best and most beloved presidents. His face is chiseled into Mount Rushmore, and his legacy is represented far wider in the national landscape thanks to his immense contributions to conservation and national parks.

Roosevelt came from a well-to-do family but was genuinely concerned about the lives and well-being of his fellow countrymen of various walks of life. He worked side by side with cowboys in the West, brought in thieves, worked personally to clean up the New York Police Department and the streets of New York City, valiantly led the Rough Riders during the Spanish-American War, and ascended rapidly through the political ranks to the presidency at the age of 42.

As a very active president, Theodore Roosevelt worked hard to help shape our country in the early 20th century. He has been especially revered by outdoorsmen and firearms collectors thanks to his contributions to wildlife and habitat conservation, his hunting exploits, and his bold masculine spirit.

Theodore Roosevelt's son, Kermit, as a child and as a student at Harvard. Kermit shared his father's love of hunting and adventure.

Guns of Theodore and Kermit Roosevelt

Though Roosevelt was involved in a variety of endeavors throughout his life, he was a dedicated family man, especially considering the era and his position within society. He ensured his children had a good upbringing, thorough education, and solid principles. Roosevelt and his second son Kermit were especially close, and they shared many of the same passions.

They both loved to hunt, explore, read, and write, and Kermit followed after his father in many ways. Like his father, he also struggled with his health in his youth, and yet he was notably more reserved and melancholy.

Theodore Roosevelt and his second son Kermit hunting in Africa after Roosevelt left the White House.

In Rock Island Auction Company's May 17-19 Premier Firearms Auction in Bedford, Texas, two lots containing firearms from the Roosevelt family remind us of the deep connection between Roosevelt and his son Kermit, their grand adventures, and Kermit’s tragic decline after losing both his younger brother Quentin and his father within a short period.

This impressive Hawken rifle from Lot 1287 packs serious firepower with its heavy .70 caliber barrel. It was most likely used for hunting big game in the American West before being given to Theodore Roosevelt. The Roosevelt family tradition states it belonged to Kit Carson.

Roosevelt’s Hunting Legacy

At their family home, Sagamore Hill, young Kermit would have seen a wide variety of firearms, including those in the Gun Room. One of those guns was a truly massive Hawken rifle. While many Hawken rifles were around .54 caliber, this beast of a gun is .70 caliber. Furthermore, the rifle is said to have belonged to none other than the famous frontiersman Kit Carson.

This historic rifle is featured on page 49 of "The Peacemakers: Arms and Adventure in the American West" by R.L. Wilson where it is described as a "Sam Hawken-made .70 caliber rifle, the most massive Hawken known" and "Likely a buffalo killer, as well as a target rifle for bench shooting. Condition and the quality of workmanship as fine as those of any known Hawken firearm."

Theodore Roosevelt no doubt told his sons stories about Carson. The frontiersman was a legend when Roosevelt was growing up as a trapper, frontier guide, hunter, soldier, and Indian fighter. We know Roosevelt took a personal interest in Carson because he bought a bronze of Carson on horseback holding a rifle as a birthday present for himself from Tiffany’s in 1915.

The Gun Room at Sagamore Hill. Note the variety of firearms on display, including several muzzleloading firearms. Many of Roosevelt’s collectible firearms were given to the Boone & Crockett Club for their collection and remained for many years before being sold, including the incredible Hawken rifle in the upcoming sale.

Young Theodore Roosevelt had been given his first gun, a Lefaucheux pinfire double barrel shotgun, when he was fourteen. By the time Kermit turned 14 in 1903, he had already fired his father’s old shotgun, dubbed “rust bore” by the family, and likely many others as Roosevelt encouraged his boys to develop their marksmanship skills.

That year, Kermit’s own side-by-side was manufactured by Parker Brothers, a 20 gauge VH Grade double barrel hammerless shotgun. Theodore Roosevelt received his first shotgun at that age, this historic Parker Bros. shotgun was likely a gift from the sitting president of the United States to his son. Roosevelt took his oldest son, Teddy, on his first deer hunt shortly before Teddy turned 14, suggesting that age was an important milestone on the road to manhood for the Roosevelt family.

Kermit Roosevelt’s Parker Brothers 20 Gauge VH Grade double barrel hammerless shotgun.

While Roosevelt was president, Kermit was hitting his formative years studying at the Groton School. As Roosevelt prepared to leave the White House, Kermit was starting at Harvard. Roosevelt wrote to his son about practicing shooting shotguns and making plans for hunting trips. Ultimately, they went on a far grander trip than had originally been discussed, but only after Kermit promised he would study hard when he returned.

In his classic account of the expedition, African Game Trails, Roosevelt dedicated the work: “To Kermit Roosevelt My Side Partner in our ‘Great Adventure’”. The book is filled with their exploits and many of Kermit’s photographs. Many of the famous photographs of Roosevelt during the expedition were taken by his son.

Theodore Roosevelt and his son embarked on an extensive safari to collect specimens for multiple museums during the Smithsonian–Roosevelt African Expedition. Roosevelt was set to write about the expedition, and Kermit served as the official photographer. They landed in Africa in April 1909 with an impressive cache of firearms and loads of ammunition ready for their grand adventure. It’s easy to imagine how formative of an experience this must have been for young Kermit exploring far-off lands and hunting massive beasts side by side with his father over many months.

The Last Adventures of Theodore Roosevelt

As promised, Kermit completed his four-year degree in just two and a half years. When he graduated in 1912, his father was running for a third term as president, first challenging President Taft for the Republican nomination and then running as a Progressive. The Progressive Party under Roosevelt’s leadership was popularly known as the Bull Moose Party.

That October, Roosevelt survived an assassination attempt when he was shot in the chest at close range. Thanks to his experience as a hunter and military officer, he was able to calmly determine that the bullet had not punctured his lung and famously went on to give his speech anyway, opening with the lines: “Friends, I shall ask you to be as quiet as possible. 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.”

Kermit no doubt feared for his father’s safety, especially considering Roosevelt had first become president because an assassin shot and mortally wounded President McKinley. Roosevelt remained undeterred, but ultimately the split between the Republicans and the Progressives handed the election to Woodrow Wilson and the Democrats.

"The Bull Moose Colt Single Action" was ordered as a gift for Theodore Roosevelt for his 54th birthday just days before he was shot while running for president in 1912 and was sold at Rock Island Auction Company for $1,466,250 in December 2020.

Roosevelt soon planned another grand adventure. He accepted an invitation to speak in Buenos Aires and then on another arduous scientific expedition to explore the uncharted River of Doubt in Brazil: the Roosevelt-Rondon Expedition. Edith Roosevelt asked Kermit to go along to look after his father. He was already in Brazil on business and left behind his fiancé, Belle Willard.

Theodore Roosevelt photographed by Kermit Roosevelt during their harrowing expedition on the River of Doubt in South America.

While the father and son were again off on an adventure to hunt and explore a faraway land, unlike their African safari, their journey on the River of Doubt was far from a pleasant experience. They were plagued by problems, including tropical diseases, serious injuries, the loss of much-needed equipment, and even the deaths of multiple members of one of their crew, including one murdered by another.

Roosevelt severely wounded his leg and was weakened by disease. He asked to be left behind to overdose on morphine in the jungle rather than risk the lives of the remaining members of the expedition, but Kermit would not leave his beloved father behind and convinced him to press on. Roosevelt is said to have never fully recovered from the perilous journey, and Kermit too must have been a haggard mess when they returned, but he went on to marry and was all too soon destined for another harrowing experience: The Great War.

Lot 371 in May's auction contains a historically identified World War I U.S. Army Air Service leather flight helmet connected with the 1st Pursuit Group, the first air combat group formed by the Air Service of the American Expeditionary Force. Theodore Roosevelt's son Quentin Roosevelt was a member of the 95th Aero Squadron in the 1st Pursuit Group and remains the only child of a U.S. president killed in combat.

The Roosevelts and the Happy Hunting Grounds

During World War I, Theodore Roosevelt offered to again lead men in combat as he had done at the head of the Rough Riders during the Spanish-American War, but he was rebuffed by his political adversary Woodrow Wilson. His sons Ted, Kermit, Archie, and Quentin, however, served in the war in different units. Quentin was a pilot and was shot down and killed, remaining to this day the only child of an American president killed in combat. Ted and Archie were both wounded but recovered, and Kermit made it home physically unscathed, but the loss of Quentin shook the family.

Theodore Roosevelt planned to run for president again, but the great patriarch of the family suddenly deteriorated, dying of what is believed to have been a coronary embolism. Some have said he died from a broken heart after the loss of his youngest boy, and others have pointed to his near-death experiences with Kermit in Brazil. Both certainly may have been major contributors. Regardless of the exact cause, his death left a major hole in the family.

Included with Kermit Roosevelt’s Parker Brothers shotgun in Lot 1501 from May's auction are four pieces of silver drink ware, including a large flask presented to him before heading out on one of his expeditions in Asia with his brother, and a silver cup from the private speakeasy “The Room.”

Kermit’s life started to fall apart after the loss of his father and brother. He had long been prone to depression as had other members of his family and faced serious financial losses during the Great Depression. He began to drink heavily and had an open affair leading to distress in the family. Like his father before him, he sought an active life and went on two hunting expeditions in Asia for ostensibly scientific purposes and wrote of the adventures in Trailing the Giant Panda and East of the Sun and West of the Moon with his brother Ted.

Kermit and his wife, the former Belle Wyatt Willard (left) and Kermit Roosevelt as an officer during WW2 (right.)

World War II again offered him the opportunity to serve. Kermit joined the British Royal Army and participated in the failed invasion of Norway, and then in Egypt. His health was severely compromised by his continued drinking, leading him to be medically discharged. Back in the States, Kermit's family had him tracked down by the FBI and committed to a sanitarium in an attempt to save him.

Through President Franklin D. Roosevelt, Kermit was given a position as a major in the U.S. Army in Alaska in the hopes that military service would help, but instead, he wanted a combat role and continued to decline, ultimately taking his own life as his father had considered in different circumstances back in Brazil. Kermit Roosevelt’s death was reported to his mother and the public as a heart attack. His remaining family may have thought about how he had crossed over to “the happy hunting grounds” where his father Theodore Roosevelt and younger brother were already waiting.

Like his father, Kermit Roosevelt wrote extensively about his hunting expeditions with his father and family. Books like 'The Happy Hunting-Grounds' provide a fascinating insight into their family life and adventures and the deep connection between father and son.