CMDR FiveStringJeff grew up as John Jefferson on LP 849-20 AB 4, an earth-like world filled with colonists from the Earth's former southern United States. As such, he grew up learning the values of hard work, good manners, & a can-do attitude. He gained a love for the stars flying with his father, a passenger liner pilot. He gained admission to the colony's military academy, graduating in 3284, becoming an ordnance & logistics specialist. However, he grew tired of the LP 849-20 military bureaucracy and left the uniform behind, opting to learn the ropes of galactic finance. He excelled in this & built his reputation with several firms in the LP 849-20 system. But after his father's passing in 3304, Jefferson began to rethink life, and in May of 3306, he applied for his Pilot's Federation license.

Jefferson's ability to play several stringed instruments earned him the nickname "Five-String Jefferson," which was shortened to FiveStringJeff. He goes by Jefferson or Jeff, but never John.