Auction offers Teddy Roosevelt’s pocket watch, lost portrait of Sitting Bull, more historical items

March 9, 2023

On March 18, Clearwater Florida-based Blackwell Auctions will hold its American Sale—featuring important historical art, documents, and artifacts from the early colonial period to the present day, according to a press release.

Among the items to be sold are Theodore Roosevelt’s pocket watch; a lost portrait of Sitting Bull; a Revolutionary War bond; official documents signed by James Madison, John Quincy Adams, Andrew Jackson, William Henry Harrison, John Tyler, and Abraham Lincoln; a book by Thomas Jefferson; a civil War letter archive; and a check signed by Annie Oakley. None of the artifacts has been exhibited or sold before.

Theodore Roosevelt’s personally owned pocket watch

Formerly the centerpiece of a private collection, an historic Waltham watch will be sold. Inside the cover is engraved “Theodore Roosevelt” and “From D.R. and C.R.R.” In her 1924 book, “My Brother Theodore Roosevelt,” Corinne Roosevelt Robinson (C.R.R.) includes a letter he wrote just prior to his engagement in Cuba. It began: “You could not have given me a more useful present than the watch; it was exactly what I wished … thank old Douglas [D.R.] for the watch ….”

In his 1914 book, “Through the Brazilian Wilderness,” the former president writes about a particularly difficult bayou crossing. “One result of the swim, by the way, was that my watch, a veteran of Cuba and Africa, came to an indignant halt.”

On the inside lid is incised a tiny mark from a watchmaker, which includes “4/16” —presumed to be April 1916—corresponding to the repair of the watch that saw San Juan Hill, an African safari, a storied presidency,

Above, a portrait of Sitting Bull by Caroline Weldon, 1890. (Photo source: Blackwell Auctions)

and a jungle expedition that nearly ended Roosevelt’s life.

Portrait of Sitting Bull by Caroline Weldon, 1890

Among the headliners of the American Sale is an oil painting of one of the most historically important figures of the 19th century, Sitting Bull, the chief who united the Sioux to defeat Custer at Little Big Horn. The portrait was one of four known to have been painted of Sitting Bull by Caroline Weldon (1844-1921), a New York-based artist who traveled to North Dakota and became his personal secretary. A fictionalized account of their relationship was the subject of a 2017 movie, “Woman Walks Ahead,” starring Jessica Chastain as Weldon.

“The cultural significance of this piece can hardly be overstated,” said Edwin Bailey of Blackwell, “because the painting represents at once the poignant intersection of two marginalized groups: the indigenous peoples of America and women artists.”

Personal items of Annie Oakley

The sale will offer several items personally owned by sharpshooter Annie Oakley, including an engraved carriage clock gifted to her for her birthday during the American Exposition in London in 1887. Several other items will also be offered, including books from her library and a signed check.

“Annie Oakley is a veritable icon of the American West,” said Bailey. “She earned the nickname ‘Little Sure Shot’ from none other than the legendary Sitting Bull. It’s such a privilege to handle these historic treasures obtained directly from her descendants.”

According to the letter of provenance (written by a direct descendant of Oakley’s niece, Irene), the clock was gifted to Oakley for her birthday while in London. Family history maintains that it was with her in 1901 when she was involved in the train disaster that injured her badly.

An outstanding signed document collection

The sale boasts a collection of important American documents from 1650 to the mid-20th century. The selection includes pieces signed by several American presidents, as well as  Mark Twain, Robert E. Lee, and dozens more.

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Research contact: @blackwellauct