Theodore Roosevelt (1858–1919) twenty-sixth president of the United States.   

Sargent's painting would be the official portrait of the President, but it wasn't the first. In 1902 Theobald Chartran was  commissioned to paint portraits of the President and his wife. Although she enjoyed her's (a feminine portrait of her on a bench outside the White House in a wide brimmed hat) Teddy simply hated his. At first they tried to hide the blasted thing in an upper corridor in the darkest place on the wall. The family called it the "Mewing Cat." Teddy disliked it so much that he eventually destroyed it. [1] 

What Teddy wanted was a man's portrait by a real man's artist. A year before the commission, Roosevelt found his man in the burly Sargent and said, "He is of course the one artist who should paint the portrait of an American President." [1] 

But Sargent wasn't going to have an easy time with the Rough Rider, trusts busting, Big Stick carrying, Panama canal building President. Teddy, having been stung once,  would take no nonsense from the artist no matter how renown he was. 

The two men surveyed the house and Sargent attempted to make sketches of his subject in various rooms trying to find the best lighting and pose, but nothing was working. This didn't sit well with the ever restless President. As they climbed the stairs to try and find a better arrangement on the second level, Teddy brusquely remarked that he didn't think Sargent had a clue as to what he wanted. Sargent, also loosing patients, shot back that he didn't think the President knew what was needed to pose for a portrait. Roosevelt, whom by then had reached the landing, planted his hand on the balustrade post, turned onto the ascending artist and said,  "Don't I!" [2] 

Sargent had found his picture. 

If a person doubts the ability of Sargent to capture the essence of the man or woman, then they have only to look at the Portrait of President Theodore Roosevelt. It was informal but strong. It was modern but respectful. It was exactly what Teddy Roosevelt wanted and he would adore the portrait for the rest of his life. It had exactly captured, in the President's eyes, the essence of his energy as well as his presidency. 

Though Sargent would eventually hit a home run with the portrait, the rocky beginnings were but telling signs of the entire commission. Teddy wouldn't stay still and would only consent to a half-hour a day after lunch. Aids and secretaries were constantly moving in and around him disrupting his concentration, and there was hardly enough time for Sargent to even reach his emotional groove for painting. [3] 
 

Notes: 
 

1) See the Whitehouse: "Art for the President's House — An Historic Perspective" by Doreen Bolger & David Park Curry  

2) "Theodore Roosevelt: Icon of the American Century;" Smithsonian Institution, with essay on the portrait here. 

3) Sargent would later paint a portait of President Woodrow Wilson in 1917 [n/a]. See Sargent's letter to Mary Hale, October 20, 1917 where he descibed the differences.

See the year in review  1903 
 

 
President Woodrow Wilson 
1917

Subject: Roosevelt "Mug" by Sargent 
From: Downie Mathis
down ieb us hey@hotmail.com>  
Date: Wed, 24 Jul 2002 
 

My grandfather tells a story of Roosevelt doing some publicity traveling with charcoal drawings signed by the President and Sargent that he handed out in his travels...gold rush??? Possibly??  He claims to remember it, and says there was a write up in a National Geographic about this.  Do you know anything about it or where I could look to find this information?  There would have been 100s of original charcoal drawings by Sargent that apparently look similar to the famous painting.  I'd like to find this article (or information on this tour) for him. 
Thanks for your help. 
 
From: Natasha 

Anyone?