Jessie was born and raised in Chicago, Illinois. He was educated at the Rudyard Kipling grammar school and Percy L. Julian High School. He earned an A.A. in Applied Science from Hutchison College (Kansas) and a B.A. in Ministry from Andersonville Theological Seminary (Georgia).

Jessie serves as a deacon, Sunday school teacher, and armorbearer to Pastors Derrick and Bonita Roberts of the Restoration of Faith Church, Flossmoor, Illinois.

Jessie is married to Cassandra Turner. He has seven children and thirteen grandchildren.