There was a “tradition” that Job Tyler was already in Andover when the first documented settlers arrived. That’s according to Sarah Loring Bailey, whose detailed accounts of Andover’s earliest happenings are incomparably described in her 1880 book, “Historical Sketches of Andover Massachusetts” (Houghton, Mifflin and Company - Boston). She speculates as to whether being here first may have given him a sense of entitlement [not her exact words]. We will never know; however, it would have taken a great deal of courage to live alone in the wilderness.
The first solid documentation of Tyler or his family occurs in 1648, when his wife was mentioned as being a victim of an accused witch, John Godfrey of Andover. The Godfrey events occur decades before the Salem witch trial hysteria. Godfrey was said to cause the Devil to appear in many shapes, and one of those shapes was a bird that “had come to suck the wife of Job Tyler, of Andover, and she and others had fallen into strange fits and sickness.” (Bailey). Godfrey was acquitted and sued his accusers for defamation, presumably including Tyler. Perhaps Tyler was ordered to pay damages to Godfrey or perhaps not, but, in 1650, Tyler mortgaged his house, land, and three cows to a Newbury man, an unusual transaction by a pioneer.
Among the first documented settlers were the Chandlers, and by 1658 Thomas Chandler was a respected blacksmith. According to him, the following events took place. Job Tyler apprenticed his son, Hopestill, to Chandler. The apprenticeship contract was drafted by a man who kept it in his house. Job Tyler, having changed his mind about the apprenticeship, entered that house and took or destroyed the contract. Tyler, of course, denied this, and apparently was never charged with theft. However, the record shows that civil litigation ensued, and the cases of Chandler v. Tyler and Tyler v. Chandler went on for over 10 years (Bailey).