Chipman was born in Inglewood, California and graduated from H. L. Bourgeois High School in Gray, Louisiana.

He then attended the United States Military Academy at West Point, earning a Bachelor of Science degree and commissioning as an infantry officer in 1980.

He was next assigned as the Deputy Staff Judge Advocate, U.S. Army Infantry Center and Fort Benning, Georgia.

In 1999, he returned to Fort Bragg to serve as Legal Advisor, Joint Special Operations Command.

In August 2014, it was announced that Chipman will serve as the chief counsel for the Republican members of the United States House Select Committee on Events Surrounding the 2012 Terrorist Attack in Benghazi.