Roosevelt, Theodore | Teddy Roosevelt wants a "Square Deal"—but isn't so sure about a presidential portrait

Roosevelt, Theodore

2 typed letters signed and one autograph letter signed ("Theodore Roosevelt") as twenty-sixth President, to William Hooper ("Dear Billy"), discussing his presidential portrait and his reelection 

2 typed letters, each one page (225 x 183 mm) on a bifolium of White House letterhead, Washington, 29 December 1902 and 2 January 1903 and one autograph letter signed, 2 pages (175 x 113 mm) on a bifolium of White House letterhead, Washington, 13 November 1904, each accompanied by its original typed or autograph manuscript, respectively; each with a horizontal fold, some other minor creasing and finger-soiling.

A Presidential portrait—and a square deal. In September 1902, Vice President Theodore Roosevelt was thrust into the White House by the assassination of President William McKinley. In the earliest letter of this group, written just three months after he took the oath of office, Roosevelt responds with some uncertainty to a suggestion made by his Harvard classmate William Hooper regarding his official White House portrait:

"I hardly know how to answer you. I suppose the fact of being President, even in the way in which I became President, will prevent the painting of a portrait from being an absurdity; on the other hand, I do not exactly feel as though I was quite entitled as yet to have my portrait as you suggest. Will you let me think over the matter for two or three days? [Attorney General Philander Chase] Knox has been anxious for the Frenchman [Théobald Chartran] who painted Mrs. Roosevelt paint me. I do not know whether he is going to give me the portrait or not. If he does perhaps I could give it to Harvard."

Less than a week later, Roosevelt has relented, writing to Hooper on 2 January 1903, "All right. The pictures shall be made, but will you let me think for a few days as to how it shall be done?" That year, President Roosevelt began short sittings for John Singer Sargent's powerful portrait, which Teddy liked "enormously."

The final letter in this series was written just five days after Roosevelt secured a presidential term in his own right, handily defeating, with his running mate Charles Fairbanks, the Democrat ticket of Alton Parker and Henry Davis. Roosevelt thanks Hooper for his assistance in the campaign and references his principal campaign slogan: "I am greatly obliged for your letter, old fellow; and I want you to understand how much I have appreciated the support of my old friends. Yes, we won out in fine shape; and now I shall do my best to give a 'square deal' administration."