[1] Despite limited educational opportunities on the colonial frontier, Haywood taught himself law and in later life became widely read.
[2] In 1794, Haywood was appointed to the bench of the Superior Court of North Carolina, but resigned in 1800 to defend a longtime friend, North Carolina Secretary of State James Glasgow, who, along with several other prominent citizens, had been charged with land warrant fraud.
Following the trial in which Glasgow was convicted, Haywood moved to Raleigh and returned to private law practice.
He built a home called Tusculum some eight miles south of Nashville and soon added two log offices.
The Civil and Political History became an influential source for future Tennessee historians, especially J. G. M. Ramsey.
In researching his histories, Haywood examined early colonial and state records and interviewed many of the pioneers or their descendants.