Kratman is a political refugee and defector from the People's Republic of Massachusetts. The mechanism of his defection was enlisting into the Army in 1974 at age 17, which deeply distressed his high school (Boston Latin, founded 1635) as they thought he had "higher and better things" ahead of him.

He served two years as an enlisted grunt with the 101st and 1.5 with the 193rd Infantry Brigade in Panama, getting 2 years of college done (when he wasn't in the field he was taking courses). At that point the Army gave Kratman a scholarship and sent him off to Boston College to finish his degree and obtain a commission. Tom graduated, cum laude, in 1980 and returned to the Army as an infantry officer.