James Whitcomb Riley was born October 7, 1847 in Greenfield, Indiana. His childhood home was on the National Road, the transcontinental highway of the 1840s. His father, Reuben Alexander Riley (1819 - 1893) was a successful lawyer and was one of the delegates to the Chicago Republican Convention of 1860 that nominated Abraham Lincoln. In 1861, Reuben left his family to join the Union Army and fight in the Civil War.
Shortly after Reuben Riley went off to war, early in the morning a man appeared at the Riley home. He had a small girl with him and he said he was her uncle and that she was an orphan. He said he could no longer support her and asked if Mrs. Riley would take her in. Her name was Mary Alice Smith. Mary Alice was only a few years younger than James, but she was small for her age. She worked for her keep in the home (as a servant) and told the Riley children stories. Less than a year later, the "uncle" reappeared, unannounced, and claimed the girl.
In one account the uncle's name is given as John Rittenhouse. He is said to have found Annie in the hills around Liberty, Indiana and took her to his home near Greenfield. Then he put her out to work dressed in black the way orphans dressed. And that's how she came to live with the Riley family.
The T in "Little Orphant Annie" is said to have been mistakenly inserted by a phonetically-challenged typesetter at the time of its publication, and it has never been amended.