This was a tumultuous time in Florida history, and Douglas met the task of restoring the rule of law to curb both criminal offenders and planters and businessmen trying to escape responsibility for their debts.

He then opened a legal practice in Tallahassee until he was appointed Collector of Customs at Key West in 1849.

His secessionist tendencies made him persona non grata to Federal authorities, and he returned to Virginia.

He served the Confederate States of America as a military judge, and returned to Florida after the cessation of hostilities.

In 1866, Governor David S. Walker appointed Douglas to replace Justice Augustus E. Maxwell.