Although I have yet to find out when exactly Howard Pyle and Theodore Roosevelt first met (the earliest known in-the-same-room-at-the-same-time instance was at a January 1896 dinner in honor of Owen Wister), by 1898 Pyle was referring to the then-Assistant Secretary of the Navy as “my friend”. Their bond, I gather, had its roots in their mutual love of history, but after 1901 Pyle also became an enthusiastic supporter of then-President Roosevelt’s policies. In addition to Pyle’s occasional visits to the White House, the two exchanged letters and favors over the years, and on the eve of Roosevelt’s turning 50, Pyle sent him the drawing shown here, which prompted the following thank-you note:
October 27, 1908.Pyle’s original pen-and-ink drawing now belongs to the Theodore Roosevelt Collection in the Houghton Library at Harvard University.
My dear Mr. Pyle:
Who could have a more beautiful birthday card? I shall prize it always for its own sake and still more for the sake of the donor.
Always your friend,
Theodore Roosevelt
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