I believe the real “Little Orphan Annie” was a woman named Anna E. Crumbaugh Kiefer and not Mary Alice Smith Gray. Here’s why:
1). “Annie” is a dimunitive form of Anna (not Mary Alice).
2) Anna Kiefer is buried in Park Cemetery (Greenfield, Indiana) and her tombstone says “Little Orphan Annie”.
3) The will record of Thomas Carr of Greenfield, Indiana lists Kate E. and John R. Keefer who are the the daughter and son of Charles and Anna Keefer. Thomas states that he is of advancing age and that he and his wife were childless and that they raised Ann the mother of his legatees. Raising another person’s child is a stong indicator that child was an orphan. Thomas Carr’s will is witnessed by Reuben A. Riley, father of James W. Riley. The Carr’s and Rileys are listed only 11 dwellings apart in the 1870 census and may have actually been neighbors.
James W. Riley was good friends with Almon Kiefer (and wrote about him in some of his poems). Almon Kiefer and Charles Kiefer were granduncles to David Kiger who also knew James W. Riley.
David Kiger, his wife and daughter, Jane (my mother), went to visit Anna Kiefer in Indianapolis around 1942. My mother, who was 6 at the time, remembers Anna as a petite woman. Anna gave my mother a two piece dress my mother played in. My mother was tall for her age and the dress was just a little long.
My family knew the Rileys and had met the woman I believe was the inspiration for Little (she was petite) Orphan (raised by people other than her parents) Annie (named Anna).
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