Blackwell Auctions’ March 18 American Sale features what made America great, as seen in art, documents signed by historical figures, and other iconic American cultural objects

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Highlights: Teddy Roosevelt’s pocket watch, Sitting Bull portrait, Annie Oakley’s clock & library items, early photographica, letters & docs signed by presidents and notables

CLEARWATER, Fla. – America’s rich cultural history is laced with heroes and scalawags, blue-blooded entrepreneurs and immigrant achievers who rose from the humblest beginnings. All who contributed to the colorful tapestry of our 246-year-old nation – whether saintly or scurrilous – are part of our nation’s story, which serves as the backdrop for Blackwell Auctions’ March 18 event titled “The American Sale.”

Theodore Roosevelt’s American Waltham pocket watch in a coin-silver case. Gifted to him in 1898 by his sister Corinne Roosevelt Robinson and engraved inside cover: ‘THEODORE ROOSEVELT’ and ‘From D.R. and C.R.R.’ Watch is referenced in detail in a thank-you letter published in Corinne Roosevelt Robinson’s 1924 book ‘My Brother Theodore Roosevelt.’ Estimate $100,000-$200,000
Theodore Roosevelt’s American Waltham pocket watch in a coin-silver case. Gifted to him in 1898 by his sister Corinne Roosevelt Robinson and engraved inside cover: ‘THEODORE ROOSEVELT’ and ‘From D.R. and C.R.R.’ Watch is referenced in detail in a thank-you letter published in Corinne Roosevelt Robinson’s 1924 book ‘My Brother Theodore Roosevelt.’ Estimate $100,000-$200,000

The 395-lot auction contains art, historical objects, and highly important signed ephemera, along with many other near-apocryphal pieces that will stun collectors. Highlight categories of the sale include a collection of deaccessioned early American through 20th century presidential documents, letters and autographs; and a collection of legendary sharpshooter Annie Oakley’s personal possessions (with family provenance). In addition, there are two single-lot items that qualify as unique American treasures: a silver pocket watch gifted to Theodore Roosevelt by his sister, and a portrait of Chief Sitting Bull whose back story served as the basis for the 2017 motion picture Woman Walks Ahead, starring Jessica Chastain. 

The Teddy Roosevelt pocket watch, a Waltham production in a coin-silver case, is well documented as having been one of the 26th president’s most cherished assets. It was gifted to him in 1898 by his sister Corinne Roosevelt Robinson and her husband Douglas Robinson and is engraved inside the cover: THEODORE ROOSEVELT and From D.R. and C.R.R. The watch is referenced in detail in Corinne Roosevelt Robinson’s 1924 book My Brother Theodore Roosevelt, which includes the text of many letters she received from him. One of those letters, dated May 5, 1989, begins: “You could not have given me a more useful present than the watch; it was exactly what I wished [for]…” Passing by descent through the Roosevelt family, then to a private collection, the one-of-a-kind watch is estimated at $100,000-$200,000.

A dignified oil-on-canvas portrait of Lakota chief Sitting Bull, painted in 1890 by Caroline Weldon (1844-1921), leads the American Art category. The portrait is one of four known to have been painted of Sitting Bull by Weldon, a New York artist who traveled to North Dakota in 1889 and became the chief’s confidante and personal secretary and remained so until 1890, when they had a falling out over his support of the Ghost Dance movement. A fictionalized account of their relationship and her interest in painting him is the subject of the 2017 movie, Woman Walks Ahead, starring Jessica Chastain as Weldon.

Of Weldon’s four portraits, one is held at the North Dakota Historical Society in Bismarck, while another is in the collection of the Historic Arkansas Museum in Little Rock. The remaining two were presumed lost until the painting to be sold by Blackwell Auctions was consigned by a descendant of its original owner, a railroad construction engineer from Minnesota. An accomplished portrait painted from life and depicting a legendary Native American, this very special artwork is expected to sell in the $40,000-$80,000 range.

Coincidentally, it was none other than Sitting Bull who bestowed the nickname “Little Sure Shot” on Annie Oakley, who also features prominently in the March 18 sale. Several items personally owned by Oakley will be offered, including a French carriage clock that was engraved with her name and gifted to her for her birthday during the American Exposition in London 1887. An Oakley biography references the clock as being one of dozens of gifts she received at the event from members of European royalty, and according to family history, it was with her during the 1901 train disaster that left her badly injured. Auction estimate: $10,000-$20,000

Other Oakley items include 16 books owned, and, in some cases, signed, by Oakley. One of them is inscribed to her husband by the author, bandleader John Philip Sousa. Also included is a 1926 personal check made out to her niece and signed with her married name “Annie Oakley Butler.” All of the Annie Oakley items to be auctioned come from a direct descendent of Oakley’s half-sister Emeline Patterson. 

There is already a groundswell of bidder interest in the sensational estate collection of historical documents and autographs. “Most of the signed documents and letters in this collection haven’t been offered for sale in more than a generation, if ever at all, and many were museum deaccessions,” said Blackwell Auctions’ owner, Edwin Bailey. Autographed items include pieces signed by US presidents: Abraham Lincoln, William Henry Harrison, Andrew Jackson, Ulysses S. Grant, John Tyler, John Quincy Adams, and FDR. Also represented are two signers of the Declaration of Independence, Civil War figures Robert E. Lee, Admiral David Farragut and Jefferson Davis; and later legends of war, Generals John Pershing and Douglas MacArthur. The signatures of literary lions Mark Twain and Walt Whitman, plus those of dozens of other notables, are found in this collection, as well. 

A dated 1863 officer’s appointment signed by President Abraham Lincoln and Secretary of War Edwin Stanton names Connecticut officer Eleazer H Ripley a captain in the 85th Reserve Corps, a non-combat unit for disabled soldiers. JSA authenticated, this prized Lincoln Civil War-era document is estimated at $5,000-$10,000. The sale also features an 80-piece archive of Civil War letters, CDVs, and a fine selection of original 19th-century images, including tintypes, daguerreotypes, and cabinet photos, many with historical subjects.

The American Art section reveals a broad spectrum of paintings and sculptures, from a Western sculpture by Frederic Remington to a charming Adam Emory Albright oil painting of a child gathering flowers. A signed, original Ludwig Bemelmans (Austrian/American, 1898-1962) ink and gouache on paper painting of his famous book-series character “Madeline” is expected to achieve $2,000-$4,000; while a much higher price is anticipated for each of two lithographs by Thomas Hart Benton (American, 1889-1975). Titled Jesse James and Frankie and Johnnie, respectively, each of the Western scenes – a train robbery and a saloon brawl – is artist-signed in pencil. Both lithographs were sourced from a section of a Missouri State Capitol mural that Benton painted in 1936. Offered consecutively, each is estimated at $10,000-$20,000.

A collection of toys and pop culture items add color and fun to the sale, with highlights including two rare 1955 PEZ plastic full-body robot dispensers, $400-$800/pair; and an exciting baseball treasure: a 1952 Bowman #101 Mickey Mantle baseball card. Freshly PSA-graded NM 7, it is estimated at $10,000-$20,000.

Blackwell’s March 18, 2023 American Sale will start at 12 noon EDT. For additional information, visit or contact Edwin Bailey at 727-546-0200. Bidding is available online through LiveAuctioneers, Invaluable, Bidsquare, HiBid and through the Blackwell Auctions app (IOS and Android), as well as absentee and by phone.

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