Blackwell Auctions Presents Rare Portrait of Sitting Bull and Teddy Roosevelt’s Pocket Watch in Upcoming American Sale

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Blackwell Auctions of Clearwater, FL will present nearly 400 curated lots in The American Sale, to be held on March 18, 2023 starting at 12:00 PM EDT. This event features fine art, collectibles, ephemera, and other historical items relating to figures such as Theodore Roosevelt, Sitting Bull, Mickey Mantle, and Annie Oakley.


Leading this event is a pocket watch given to Theodore Roosevelt by his sister, Corinne Roosevelt Robinson, in 1898 (lot #250; estimate: USD 100,000 – $200,000). An American Waltham watch in a coin silver case, this item bears a personalized engraving and Roosevelt’s name in block letters. The 26th American president took the watch with him to Cuba and possibly on later trips to Africa and Brazil. The piece formerly belonged to a Buffalo, NY collector, purportedly since the 1980s. 

ANNIE OAKLEY, Engraved Carriage Clock
ANNIE OAKLEY, Engraved Carriage Clock

Another notable clock in this sale is an engraved French carriage clock gifted to Annie Oakley on the occasion of her birthday (lot #200; estimate: $10,000 – $20,000). A member of the European royalty likely presented the gift to Oakley during the 1887 American Exposition in London. By this time, Oakley had already joined Buffalo Bill’s Wild West as a sharpshooter and performer. She had become a star both at home in the United States and abroad. This clock, with a courting scene painted on the face, was reportedly with Oakley during a serious train accident in 1901. 

Portrait of SITTING BULL, Caroline Weldon, 1890
Portrait of SITTING BULL, Caroline Weldon, 1890

A portrait of Sitting Bull, the Lakota Sioux leader and Oakley’s colleague from Wild West, is another notable item in the sale (lot #100; estimate: $40,000 – $80,000). This oil on canvas was completed by Caroline Weldon. A Swiss-American artist and activist, Weldon was Sitting Bull’s personal secretary and confidante during the late 1880s. Beyond the available work, she completed four known portraits of the warrior and leader, all of which reside in museums or have been lost. 

Additional lots of interest include: 

  • A 1952 Mickey Mantle Bowman card, graded Near Mint by the Professional Sports Authenticators (PSA) (lot #80; estimate: $10,000 – $20,000) 
  • Thomas Hart Benton’s lithograph of Jesse James (lot #222; estimate: $10,000 – $20,000)
  • An antique Watling ROL-A-TOP five-cent slot machine (lot #12; estimate: $4,000 – $8,000) 
  • A $1,000 Federal Reserve bill from 1934 (lot #14; estimate: $2,000 – $4,000) 
  • A 45-star American military flag from circa 1900 (lot #92; estimate: $600 – $1,200) 

Blackwell Auctions, LLC is a family-operated business owned by Edwin Blackwell Bailey and Shannon Bailey. The name stems from Edwin’s great, great grandfather, Blackwell Bailey. Blackwell Auctions is becoming known for carefully selecting distinctive items for its sales, ranging from fine art, jewelry, militaria, coins and stamps, to furniture, sterling silver and more. Single items, collections and estates are purchased or accepted on consignment.The American Sale will begin at 12:00 PM EDT on March 18, 2023. To view the complete catalog and register to place a bid, visit Bidsquare.

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