Sidney is a 2008 graduate from the University of Tennessee with a bachelor’s degree in agriculture science and a major concentration in agricultural business and economics. He spent much of his time over the last 11 years at the Farmers Cooperative in Tennessee.

Sidney married college sweetheart Melinda on June 19, 2010. Together, they have two boys Landon Allen Jessee, 6, and Logan James Jessee, 3. He and his family are members of the Tater Valley Community of Luttrell, TN and Luttrell Missionary Baptist Church.

Sidney currently serves on the Union County Commission, representing the 2nd district. His hobbies include hunting, fishing, farming, playing bluegrass music, and watching his boys play t-ball.