Robert "Bobby" Schilling was born and raised in Rock Island, Illinois.He has been married to Christie for 24 years and together they have 10 children: Terry, Aaron, Levi, Joe, Isabel, Rachel, Olivia, Sam, Sophia, and Anthony. Bobby graduated from Alleman High School and attended Blackhawk College. Afterwards Bobby worked at Container Corporation of America. During his term there, 1983-1987, he served as a union steward in the local 191 United Paperworkers International Union. From 1987 until 1995, he went to work in the insurance and financial services industry for Prudential Insurance Company. While at Prudential, Bobby served as Treasurer for the United Food and Commercial Workers Union.