Abraham Lincoln formed some very close friendships with several citizens of Pittsfield. Among the most prominent ones were Milton Hay, John Milton Hay, and John George Nicolay. Milton Hay was born in 1817, and he moved to Pittsfield in 1840. He was the first law student of Abraham Lincoln. He married Catherine Forbes in 1851, and they lived in this Greek Revival brick residence. Milton's nephew, John Milton Hay, came to live with them and while in Pittsfield attended a brand-new private academy, which promised a preparatory school education. Milton and Catherine had two children who both died in infancy. Catherine died in 1857, and the next year Milton moved back to Springfield. John studied law in his uncle's office, next door to Lincoln's office. After Lincoln was elected president, he hired John George Nicolay to be his private secretary and, because of Milton's recommendations, he also hired John Milton Hay as an additional private secretary.
The house was constructed from 1838 to 1843 by William Watson, the first settler of Pittsfield and a man of considerable wealth and influence. After living elsewhere, Watson returned in 1858 to live with his daughter and son-in-law, Rev. George and Ellen Barrett, the parents of Oliver Barrett, who owned the largest private Lincoln collection of the twentieth century. During the time that
Watson did not reside in this house, Milton Hay did.
John Milton Hay was born in 1838 in Salem Indiana. His parents were Dr. Charles and Helen (Leonard) Hay. For improved schooling, Dr. Hay sent John to the Thompson Academy in Pittsfield, the county seat of Pike County, Illinois, where his lived with his uncle, Milton Hay. At the Thompson Academy, John met John George Nicolay, an editor at the Pike County Free Press newspaper. John Hay worked there on occasion, and it was there that he wrote the first draft of his famous book The Pike County Ballads. (Some of its characters were interesting people he had met while in Pittsfield.) After leaving Pittsfield, John continued his studies in Springfield, Illinois and at Brown University in Rhode Island, where he graduated in 1858. Later in life he would co-author with Nicolay the very popular Abraham Lincoln: A History (1890).