The first record in regulations to prescribe a flag for the President was the 1858 Signals for the Use of the United States Navy, which specified that the union jack (the canton of the national flag by itself, i.e. blue with white stars for all the states) should be flown at the mainmast to signify the presence of the commander-in-chief.
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Edward C. Kuhn, a designer of many early U.S. Army insignia and coats of arms, made a series of watercolors of older presidential flags.
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:For other presidents' standards, see Presidential Standard.
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Afterwards, this led to discussions on the situation which (among others) included Assistant Secretary of the Navy Franklin D. Roosevelt and the Aide to the Secretary of the Navy Byron McCandless.
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In 1945, one of the changes ordered for the similarly arranged Flag of the President of the United States by President Harry S. Truman was having the eagle face towards its right (dexter, the direction of honor) and thus towards the olive branch.