Stephenson was well-connected, and received letters from prominent people, including Jefferson Davis in 1834. That same year, Stephenson was elected to his first public office, the Illinois State Senate, after which he sought an appointment to the Land Office in Galena. From December 1834 until April 1835 Stephenson was absent from Galena. He spent time in St. Louis, where he married Ellen Kyle in December, then traveled on to Edwardsville and Vandalia, Illinois; the couple eventually had two children. In April 1835 the couple returned to Galena where James took office as Register of Lands at Galena and Chicago, and they lived an elegant lifestyle.