That is not Roosevelt's handwriting. Clearly addressed by by J. Dunlop while Roosevelt was still governor of New York. Possibly/probably an autograph request. It was a year before he ran for president so not likely someone anticipating he would win that election.
The Anna Eleanor Roosevelt cover is called a free frank. Most common among congressmen and senators. They would only need to sign their name in the upper right corner of an envelope and it would be mailed by the post office for free. They would also need to add 'm.c.' or 'u.s.s.' after their signature It is still done today. You will see bulk mailings from your senator or congressman and his signature will be printed in the upper right corner. This can only be done for official government business not election related items. Presidents and first ladies retained this right after they left office. I have never seen a presidential one post term, but first lady ones are around. I owned a Grace Coolidge one and have seen Edith Bolling Wilson.
Note that the Eleanor Roosevelt one is a stamp and not real signature.
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'Integrity is what you do when no one is looking'
"The man who can keep a secret may be wise, but he is not half as wise as the man with no secrets to keep”
Last edited by Michael B; 10-26-2021 at 01:22 PM.
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