This is an incredibly rare opportunity to get your hands on a historic firearm documented from the Roosevelt family gun collection, especially one dating to 1903 during Theodore Roosevelt's presidency. The historic shotgun and silver drinking set were owned by Kermit Roosevelt (1889-1943), the second son of Theodore Roosevelt and his second wife Edith Kermit Carow, and includes pieces from different periods in his life, including what was likely his first shotgun. It is accompanied by documentation from 1970 confirming the sale of the shotgun to Herb Glass by Kermit Roosevelt's second son J. Willard Roosevelt on behalf of the Estate of Belle W. Roosevelt (Kermit's wife) as well a 1967 letter discussing Herta Carla Peters's sale of the silver cup and her remembrance of "The Room," a private speakeasy formed around 1931 with Kermit and Theodore Roosevelt Jr. and Vincent Astor among the small number of members and frequented by them and their "lady friends (never the wives)" before it closed in 1938. Peters was Roosevelt's long time mistress, and a postcard with a photo of the couple is included. She indicated the design on the cup was the crest drawn by Carl Rungius for "The Room," and the silver cup was taken by Kermit Roosevelt as a memento when it closed. She had his cup and also one with her name on it and was hesitant to sell his. In an included letter to Peters from Roosevelt on the letterhead of the Machine Gun Training Centre at The Barracks, Mill Hill, he discusses how he missed her and the training, including that "machine gun warfare has changed a lot." An included clipping from the New York Times in 1939 shows him conducting machine gun training. Also included is an inventory of Richard P. Mellon's Theodore Roosevelt collection signed by Herb Glass as Mellon's agent listing among the items the shotgun, flasks, and cup. The shotgun is mentioned briefly in the chapter "The Omen of Death in the Moyowosi" in R.L. Wilson's "Theodore Roosevelt: Hunter-Conservationist." Greg Martin writes, "Early in 1985, I purchased the largest group of Theodore Roosevelt firearms and related memorabilia in private hands, from the Richard Prosser Mellon Collection. Included were guns from Roosevelt's exploits in the Wild West, mementos from his White House years, and...a combination over-and-under rifle-shotgun, given to the President by renowned gunmaker Fred Adolph of Genoa, New York. The collection also included Kermit Roosevelt's Winchester Model 1895 .405 big game rifle, as well as his Parker shotgun, and the uniquely notable Holland & Holland .500/.450 Royal Grade Double Barrel Rifle, presented to TR by admiring British citizens for the historic 1909-10 East African safari." While this shotgun remains, Kermit's Winchester Model 1895, TR's presentation combination gun, and a Colt Single Action Army were destroyed in a deadly fire in Africa in 1986 during the production of the documentary film "In the Blood" inspired by Theodore and Kermit Roosevelt's famous East African safari. The double rifle was spared thanks to delays and is now contained in the Frazier Historical Arms Museum. This shotgun is one of the few Roosevelt firearms remaining in private hands. Many of the other surviving firearms, including other pieces from the Mellon Collection, are now off-market in institutional collections, such as TR's Nimschke engraved Frontier Six Shooter Single Action Army and Winchester Model 1876 carbine in The Autry Museum of the American West, and various other pieces are located at various national parks and historic sites connected to Theodore Roosevelt such as the Sagamore Hill National Historic Site which previously displayed many of the firearms from Theodore Roosevelt's arms collection, including the Hawken rifle featured in Lot 1287. The shotgun is one of 4,988 Parker Bros. VH grades in this configuration and was built in 1903 with blued steel barrels with a single nickel bead sight on the matted concave solid rib which is marked “PARKER BROTHERS, MAKERS, MERIDEN, CONN. VULCAN STEEL. ” standard markings, and chambers measured at 2 3/4 inches with single extractor. The barrels are fitted to a casehardened boxlock action featuring double triggers, an automatic tang mounted safety, and light zig-zag border engraving. The gun is mounted with a lightly figured and multi-point checkered forend with Deeley latch release as well as a pistol grip stock with Parker grip cap, silver inscription shield marked “K.R.” for Kermit Roosevelt, and a red rubber recoil pad with black spacer. Barrel and stock measurements (R/L): bore diameter nine inches from the breech .620/.619 inches; choke constriction .002/.027 inches; minimum wall thickness .040/.038 inches; 1 3/4 inch drop at comb; 2 1/2 inch drop at heel; 13 7/8 inch length of pull; weight 6 lbs. 2 oz. The silver drinking set includes a 4 gill Tiffany & Co. flask with the Roosevelt family crest and "QUI-PLANTAVIT-CURABIT" motto one side and "KERMIT ROOSEVELT/APRIL 10, 1925/'BON VOYAGE AND GOOD HUNTING'" over five signatures, a cup with Asian calligraphic hallmarks on the bottom an engraved scene of a moose drinking at a bar with a bear for a bar tender over "MR. K. ROOSEVELT", a jigger marked "K" and "H", and an "ASPREY/LONDON" pocket flask inscribed "K.R" on one side and "Major/Kermit Roosevelt/From/H.C.P./10-10-39" on the other. Kermit Roosevelt was very close with his father and shared many of his interests, including hunting, adventure, reading, and writing. Like his father, he had poor health as a boy but overcame it though he remained quiet and often melancholy throughout much of his life and appears to have suffered from some of the same mental health problems as other members of his family. The shotgun dates to when he would have been around 14 years old towards the end of his father’s first term as president and would be an appropriate gun for a young hunter. Theodore Roosevelt had been given a Lefaucheux double barrel shotgun as his first firearm in 1872 by his own father when he was the same age, so it seems likely this shotgun was a gift to Kermit from the president. When his older brother Ted was about to turn 14 in 1901, Roosevelt wrote to John Burroughs informing him that Ted had killed his first buck providing further evidence of the age of 14 being an important milestone for the Roosevelts. In “The Long Trail” and “The Happy Hunting-Grounds,” Kermit wrote about his father’s troubles using a shotgun due to his eyesight but noted that he used a shotgun as a boy and young man and that “He continually encouraged us to learn to shoot with the gun” and that when he was eight he had done some bird shooting with his father and brother at the Great South Bay. He notes “I had a venerable 12-bore pin-fire gun, which was the first weapon father ever owned,” and didn’t have much success with “rust bore” as the family called it. The use of shotguns for collecting specimens and meat is also noted in both of the books along with others by Kermit. In a letter to Kermit on May 22, 1907, T.R. wrote, “I will write to Mr. Hughitt about the prairie chicken shooting and find the day that it opens. My belief is that you would not get either black bear or timber wolf if you were able to go after them, and that the prairie chicken shooting will give you just the experience that you ought to have with the shotgun. I have always been sorry I did not learn to shoot with the shotgun, because there is so little chance to do anything with the rifle, and the chance grows less year by year. Your loving father, TR.” In a follow-up letter he wrote, “When you come back I will go over with you the whole hunting trip question. I strongly advise a new double-barreled shotgun. My impression would be that if the time is ripe this would be a first-class year to try for the chicken shooting; then I will later be able to arrange some regular big game hunting for you. Perhaps when I get thru being President we will be able to take a trip together to Newfoundland, or south Yellowstone if the elk hunting is good.” While Roosevelt had downplayed his use of shotguns, he used one identified as a Parker Brothers double barrel during his time in the West and was photographed on guard with it when he captured three boat thieves in 1886 (see pages 58-59 of "Theodore Roosevelt: Hunter-Conservationist"). Kermit came of age while his father was in the White House, and he was a 19 year old college freshman attending Harvard when Roosevelt left office in 1909. His father indeed took him on a hunting trip, one far grander than Newfoundland or even Yellowstone. He accompanied his father on the famous Smithsonian-Roosevelt African Expedition that year and served as the official photographer of the expedition. T.R.’s book “African Game Trails” about the adventure features many of his photographs and was dedicated “To Kermit Roosevelt My Side-Partner in our ‘Great Adventure’.” During their adventure, a Fox shotgun was used by the Roosevelts for hunting birds for the pot, and other members of the expedition also hunted with shotguns. The big game hunting was naturally done with rifles, and the expedition as a whole collected around 23,151 specimens of a wide variety of African flora and fauna for scientific study. T.R. and Kermit together shot 512 large animals collected across great distances. Since the African safari required a leave of absence from the university, his father made him promise to study harder upon his return, and he fulfilled his promise and graduated in less than three years. After completing his studies, he went on an even more arduous adventure with his father in South American in the Roosevelt-Rondon Scientific Expedition exploring the River of Doubt, now known as Rio Roosevelt. During their adventure, the former president was injured and Kermit tended to him. When T.R. asked to be left behind and planned to complete suicide by morphine overdose rather than risk the safety of the rest of the crew, Kermit refused to leave his father and persuaded him to continue on. T.R.’s health never fully recovered, but he still attempted to serve during World War I but was rebuffed by President Wilson. However, his sons Theodore Jr., Kermit, Archibald, and Quentin all served, and Kermit was the only one to survive the war without injury. Between the River of Doubt debacle and his military service, Kermit married Belle Wyatt Willard and was the assistant manager at the Buenos Aires branch of First City Bank in 1914-1916. He took command of a British light-armored battery in Iraq earning the British War Cross for gallantry and then joined the American Expeditionary Force as a captain in the 7th Field Artillery in the 1st Division. His youngest brother Quentin never returned home. He was a pilot in the 95th Aero Squadron's 1st Pursuit Group and scored one confirmed aerial kill before his Nieuport 28 was shot down behind German lines during a large aerial engagement during the Second Battle of the Marne. He remains the only son of a U.S. president killed in combat. The heartache is said to have further led to Theodore Roosevelt's health decline and then his death in 1919. When he returned home, Kermit formed the Roosevelt Steamship Company and continued to travel. The larger flask in this set relates to Roosevelt's 1925 expedition to Central Asia with his brother Theodore Jr. (the James Simpson-Roosevelts Asiatic Expedition) which was sponsored by the Field Museum of Natural History in Chicago. The men mentioned on the large flask were friend and business associates of Roosevelt's. For example, Van Santvoord Merle-Smith, whose name is on the upper right of the flask, was an investment banker at Roosevelt & Son. Merle-Smith also served in World War I and World War II and was Third Assistant Secretary of State in 1920-1921 in the Wilson administration. Like his father before him, Kermit wrote extensively about his adventures publishing multiple books, including "East of the Sun and West of the Moon" and "Trailing the Giant Panda" with Theodore Jr. about their trip to Asia in 1925 and the Kelley-Roosevelts Asiatic Expedition in 1929. He also edited other books on exploration, contributed articles and book reviews, wrote chapters to other books, and wrote regularly for the Audubon society as the president of the organization in 1935-1937. He was also the vice president of the New York Zoological Society in 1937-1939. The pocket flask and letter dates to World War II when Roosevelt used his connections with Winston Churchill to join the Royal Army and participated in the failed summer raid into Norway and performed admirably and was then sent to North Africa where he grew bored. Kermit had a lifelong battle with depression complicated by the loss of his father and younger brother, and, by the 1930s, he was an alcoholic and had taken on Herta Carla Peters as his mistress much to the distress of his family. In North Africa, the alcohol got the better of him and led to him suffering from an enlarged liver and a recurrent bout with malaria, and he was sent back to England in late 1940 and medically discharged against his protests early in 1941. He vanished when he returned to the States and was tracked down by the FBI on behalf of the family. His family had him committed multiple times to clean him up, but he kept returned to boozing and his affair with Peters upon being released. The FBI found him heavily drunk in California and quoting the poem “Richard Cory” by his friend Edwin Arlington Robinson which told of a man who “one calm summer night went home and put a bullet through his head.” The family arranged through his cousin President Franklin Delano Roosevelt to have him re-appointed as an officer in the U.S. Army hoping it would give him purpose, and he was assigned as an intelligence officer with the rank of major at Fort Richardson in Alaska. Despite their efforts, Kermit’s mental and physical health continued to decline. He complained of being excluded from combat duty and was forced to go on leave to receive treatment for liver problems and internally bleeding. He continued drinking and tragically completed suicide by shooting himself at the fort on June 4, 1943. His death was reported to his mother and the public as from a heart attack. His 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. Provenance: Kermit Roosevelt; The Estate of Belle W. Roosevelt; The Herb Glass Collection; The Richard P. Mellon Collection; Property of a Gentleman

Fine overall, retaining 85% original blue finish with some rubbing near either muzzle, attractive smooth silver patina on the action with some traces of original case colors in the protected areas, a few light handling marks, and scattered minor spotting across the metal surfaces. The wood is also fine with a few light dings and scratches, some chattering at the front of the pistol grip, some areas of minor chipping at the wood to steel junctions, and overall crisp checkering. Mechanically excellent. The silver displays attractive aged patina. The items have some dings and dents, and the cup is more heavily dented and has a vertical split to the lip. This is an incredibly historic set of artifacts owned by Theodore Roosevelt's beloved son Kermit Roosevelt, his hunting partner in Africa and savior on the River of Doubt. A true national treasure!