"If I may write so intimately, I would like to say that it [is] my strong and personal belief that you will stand forth in history as one of the very greatest of our presidents, and it is a matter of pride and joy to me to think that one whom I believe I may regard as a friend should be destined to descend into the future as so dominant and so inspiring a figure." (Howard Pyle to Theodore Roosevelt, September 11, 1907)The admiration went both ways, however, and in honor of Presidents Day, here are some things Roosevelt said to or about Pyle:
"This note introduces a particular friend of mine, Mr. Howard Pyle, the writer. He is a first-class fellow in every way and I commend him to your courtesy." (Letter to Captain W. H. Brownson, June 11, 1903)
"You can hardly imagine, my dear fellow, how much I prize your good opinion, and how loath I should be to forfeit it." (Letter to Howard Pyle, July 5, 1904)
"One of the very best men I know anywhere, one of the pleasantest companions, stanchest friends, and best citizens, is Mr. Howard Pyle, the artist.... he is as good a man as there is in the country." (Letter to Gifford Pinchot, September 9, 1907)
"One of the pleasantest features of our time in Washington has been the friendship of you and dear Mrs. Pyle."
(Letter to Howard Pyle, February 19, 1909)
I've often wondered what Pyle would have made of the three-way presidential race of 1912. As he was a lifelong Republican (though there's a chance he turned Mugwump and voted for Grover Cleveland, a Democrat, in 1884), I doubt he would have considered voting for Wilson. And he believed in Taft because he thought Taft would "[carry] forward the work which [Roosevelt had] so magnificently begun to an equally magnificent fulfillment" (Pyle to Taft, November 5, 1908) - something that Taft didn't really do, after all. So I think Pyle's idolatry of Roosevelt (and his somewhat progressive tendencies) would have trumped party loyalty, and he would have become a Bull Mooser and followed Roosevelt wherever he went.