Lot 250 in The American Sale on March 18 may well be the most historically significant item we’ve ever handled: Teddy Roosevelt’s personal pocket watch, a gift from his sister, Corinne, given to him in 1898. Frankly, it’s not much to look at. It’s a simple American Waltham in a coin silver case. No fancy engraving on the outside. Inside the cover is engraved “Theodore Roosevelt” and “From D.R. and C.R.R.”

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In her 1924 book, My Brother Theodore Roosevelt, Corinne Roosevelt Robinson (C.R.R.) includes a number of her brother’s letters, including one written just prior to his engagement in Cuba. His May 5, 1898, letter 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 – and for his many, many kindnesses.”

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.” In their 2018 book, Theodore Roosevelt: A Literary Life, the authors reference a letter in which Roosevelt, just before departing for Cuba, “thanked his brother-in-law Douglas Robinson for sending a Waltham watch, one he would use in battle to gage precisely what he would call his ‘crowded hour’ …”

On the inside lid is incised a tiny service mark from a watchmaker, which includes “4/16” – presumed to represent April 1916 – corresponding to the needed repair of the watch that had seen San Juan Hill, an African safari, a storied presidency and a South American jungle expedition that very nearly killed him.

From a Buffalo, N.Y., private watch collection, obtained in the 1980s. After Theodore Roosevelt’s death in 1919, his wife, Edith, gave away many of his personal possessions to family members and friends. It is unknown, at present, as to who received this watch originally — the family of Kermit, Theodore Jr., Ethel or someone else. Many of TR’s personal items have reached the auction market since at least the 1950s including — most recently — an engraved Smith & Wesson pistol and a presentation hunting knife.

We needn’t mention what an honor it is to handle it.

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