FRANK JAMES Awaiting his second trial in a year, the famous outlaw writes a loving letter to his 7 year old son Robert ("My Dear Little Man") Autograph Letter signed: "Your Father/Frank James" in pencil, 1 pages, 5½x8½. No place, 1884 February 29. Written in block letters to "My Dear Little Man", in full: "I want you to hurry up and learn to ride so you can get you a new saddle. I want you to learn to write and write me a letter. Addressed in verso to "Robert F. James/at home". This letter was enclosed with a letter James wrote to his wife Annie. Accompanied by printed chart titled "The Deaf and Dumb Alphabet", showing the appropriate hand signals. Notation in Frank James' hand: "For Rob". FRANK JAMES (1843-1915) and his brother Jesse James fought as Confederate guerrillas in Missouri ("Quantrill's Raiders") during the Civil War. They joined Cole Younger and others in 1866 to form a gang led by Jesse, robbing banks and trains. Frank and Jesse survived and escaped the failed Northfield, Minnesota bank heist of 1876, forming a new gang.

ANNIE OAKLEY Carte de visite signed by Oakley for friend Ed Goodman, Buffalo Bill's nephew, who was part of the Wild West show Photograph signed: "Annie Oakley". Sepia, 4½x6½ carte de visite. Annie Oakley (1860-1926, born Phoebe Anne Moses in Darke County, Ohio), was born to a Quaker family and began to shoot rabbits and quail at age nine. Within five years, she was a breadwinner for her family as a markswoman, and, at age 15, she saved her family's farm with income she had earned from shooting game. On August 23, 1876, at age 16, Annie married Frank Butler, a vaudeville performer who became her partner. Annie's self-effacing personality (on and off stage) made her a popular performer. In 1885, the Butlers joined Buffalo Bill Cody's Wild West Show, where Annie was a star for 17 years. The five-foot-tall Oakley got her name "Little Sure Shot" from Sitting Bull and used it in her promotional materials. In 1901, she and her husband decided to retire from public life. However, shooting was in her blood, and the Butlers continued to make appearances around the country.

ANNIE OAKLEY Extremely rare signed postcard photo of her dressed as an Indian! Postcard Photograph inscribed and signed: "Annie Oakley as a Sioux/Maiden admires her/new head gear./A Merry Christmas/to Laforrds & Family". Sepia, 5½x3½. Annie Oakley (1860-1926) was born Phoebe Anne Oakley Mozee in Ohio. She was the sixth of eight children. At the age of nine she began to shoot rabbits and quail and was almost a dead shot from the first. Within five years, she was a breadwinner for her family as a markswoman. In 1876, at age 16, she married Frank Butler, a vaudeville performer who became her partner. Annie's self-effacing personality (on and off stage) made her a popular performer. In 1885, the Butlers joined Buffalo Bill Cody's Wild West Show. Annie, a star with the show for 17 years, charmed Kings and Queens. The five-foot-tall Oakley got her name "Little Sure Shot" from Lakota Sioux Chief Sitting Bull, who was briefly a part of the show in 1885, and used it in her promotional materials.In 1901, she was severely injured in a railroad wreck that temporarily paralyzed her.

COLE YOUNGER Plains Indian "peace pipe", an heirloom given by Younger to his close friend Harry Hoffman, who attended Cole at his death bed. This well-used Minnesota red pipestone comes from Hoffman's collection, with a notarized statement signed by him. Ephemera, unsigned. Catlinite pipestone "peace pipe", each separated piece roughly 8x3½ (due to length of handle), with the much-handled patina of an authentically used pipe (very different from the clean surfaces found on souvenir pipes). This easily worked rock type, drawn from quarries near the Pipestone River in Minnesota, was in use by several Plains Indian nations for making ceremonial pipes. "Catlinite" is a descriptive term applied to the stone since American painter George Catlin wrote about it in 1832. Accompanied by Typed Statement signed: "Harry C. Hoffman", in full: "one Indian peace pipe, given to Harry C. Hoffman by Cole Young", 7¾x4¾. Notarized by Charles Wright at Oxford, Ohio, September 21, 1948. COLE YOUNGER (1844-1916) was a Confederate guerrilla fighting in divided Missouri during the Civil War. Joining the band of William Quantrill, he participated in the bloody raid on Lawrence, Kansas.

EMMETT DALTON The only surviving Dalton Gang member signs this letter regarding his new book and wanting to hang a photo relating to the James Boys in his den, dated 1931 Typed letter signed: "Emmett Dalton", 1p, 8x10. No place, June 19, 1931 . To Marx Reimers, St. Paul, Minnesota. In full: "Thank you very kindly for your letter of June nineteenth, with enclosures. I am sending you an autographed photograph of myself, taken about ten years ago. The story 'West of 96' is published by Doubleday, Doran and Company, Garden City, New York, and is on sale at most all the large book stores and many department stores also. It is published under the title of 'When the Daltons Rode' and is about 80,000 words, illustrated, and much more complete than 'West of 96' which is about half that length. I would be pleased to receive a photo of the arch from which you say the James Boys started, for my private 'Den'. With Kindest regards." Emmett Dalton (1871-1937) and his three brothers led a murderous gang of train robbers, who used a network of informers and hideouts to evade a widespread manhunt.

WILLIAM F. CODY ("BUFFALO BILL") 4x5 photo of Cody, signed and signed on the 7x9 photo mount in 1903 as both W.F. Cody and Buffalo Bill Photograph Mount inscribed and signed: "W.F. Cody/'Buffalo Bill'/To Ormsby Trench/1903". B/w, 7x9 overall, image 3¾x5½ (two surfaces). Photo by Marceau Studios, 258 Fifth Avenue, New York. William Frederick Cody earned the name "Buffalo Bill" for killing thousands of buffalo as a hired hunter in 1867 and 1868. Cody's theatrical career was launched in 1872 with re-enactments of Indian battles. By 1883, he formed his first Wild West spectacle, becoming a master showman. Vintage mount is lightly foxed, soiled and slightly stained with some wear at edges. Photo is lightly soiled and slightly foxed. Signature and inscription in fine condition.

ANNIE OAKLEY Her rare, handwritten letter to family members, discussing her health and family finances. signed as "Missie." ALS: "Affect Missie/xxx/xxx", 2¼ pages, 6x9½. Cambridge, Maryland, no year October 11. On letterhead of The Dixon to "Dear Fern And Sister". In full, with original spelling and grammar: "Yours rec. Jimmie is here with me. Will forclose the Mortgage on the Mag[illegible] farm. Will turn it all over to Calvin Harrington for I am to much in to bother & I would love to have A Lawyer to make out the necessary papers so I will just turn it all over to him. But I will stay here & rest for A while. We have hot & cold water, plenty clean linen & food not bad here. Want to visit the Andrews before leaving. Jimmie brought my breakfast up this morning my heart is bad, but I will rest more after he goes south, And maby he will also. She has climbed the stairs 10 times to day & it is 11 Am now. He loves you. Bonnie, Irene, and Bessie, far more then his own flesh & blood, and would do more for either of you, of this I am sure.

WILLIAM F. 'BUFFALO BILL' CODYThe man known for his showmanship and scouting skills signed this handwritten letter concerning his financial issues. Various close associates liquidate Cody's assets so that he can pay his creditors. Autograph Letter Signed: "W. C. Cody" one page both sides, 8.5 x 11, Chicago Shan-Kive and Round-Up letterhead. Dated September 18, 1916. Letter to his attorney Henry Hersey regarding his grim financial situation. In Part: “They can explain this situation to you better than I care for they have not kept me well footed. But if you do not hear from them, I'll write you all I know. First Link got judgement for about $11,800. And sold the Irma hotel and four lots and bid it in him self. I have until Jan. 15th 1917. In which to reclaim the property. There separately he sold the fixtures, paintings, etc - I furnished the money and had W.L. Walls bid them in for me. Then Link advertised and sold a hotel of mine called Pahaska Tepee. I furnished the money and had Walls bid that in for me.

JOSEPHINE "JOSIE" EARP Very content-rich ALS to the man writing the manuscript of Wyatt Earp's autobiography, and mentioning help they are getting from Western actor William S. Hart. While urging author Flood to keep the story clean and to finish it soon, she reminds him of several more events in Wyatt's life he must include. Autograph Letter signed: "Your friends/Earps", 3 pages (12x8 integral leaf and 8x6 unattached page). Vidal, California, 1925 November 9. To John H. Flood, Jr., Los Angeles. In full: "Your letter came Monday. And I was glad to hear from you also good news. Although I am sure disappointed. And yet I still feel grateful to have them find the oil. I was in hope they would bring in a two or three hundred barrel well. But - as I said I must be satisfied as it could have been a bust too. I have been watching the oil news very closely but saw no account of it. I hope it will not be a mistake. Now when we get the story also picture we will then be ready to settle down. We had a very fine letter from Bill [friend and actor William S.