American Sale to Include Teddy Roosevelt’s Pocket Watch and a Lost Portrait of Sitting Bull

Blackwell’s March auction will offer historical items never exhibited or sold anywhere

CLEARWATER, Fla., March 8, 2023 /PRNewswire/ — On March 18, 2023, Blackwell Auctions will hold its American Sale, featuring important historical art, documents and artifacts from the early colonial period to the present day.

Theodore Roosevelt’s personally owned pocket watch

Formerly the centerpiece of a private collection, a 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 and a jungle expedition that nearly ended Roosevelt’s life.

Portrait of Sitting Bull by Caroline Weldon, 1890

Among the headliners 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 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, with 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 that belonged to Annie Oakley

The sale will offer several items personally owned by 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.

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 Abraham Lincoln, William Henry Harrison, Mark Twain, Robert E. Lee, signers of the Declaration of Independence, and dozens more.

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.

SOURCE Blackwell Auctions