Chester was born in St. Louis, MO and is a native of East St. Louis IL. He graduated from Lincoln Senior High School and attended Jackson State University in Jackson, Mississippi and Lincoln University in Jefferson City, MO. He joined the U.S. Navy in 1988 and was honorably discharged in 1994. He joined the U.S. Army National Guard in 1995 and was honorably discharged in 1997. He worked as a private contractor for the country of Kuwait in the Middle East, providing support for the F/A 18 Jet Aircraft. After returning to the United States, he worked with at-risk youth via St. Louis Job Corp. During that time, he once again received a call to return and serve his country and he re-enlisted in the United States Navy where he relocated to San Diego CA. Due to an injury during the Gulf War, Chester retired from the service.

He moved to Phoenix, AZ in 2000 to be closer to family and his brother. He has 13 years of employment service experience working for non-profit agencies, for-profit, and state government agencies. Chester has received his employment training from the University Of Denver, CO, the United States Department of Labor and the National Veterans Training Institute.

He takes great pleasure in helping the individuals he serves become successful in achieving their goals and pursuing their dreams.