Grogan and his fellow sea marshals realized even crew members could be members of Al Qaeda or Al Qaeda supporters. The ships sea marshals protected consisted of oil tankers; container ships, cruise ships, and bulk carriers. These ships came from all around the world. Grogan transferred military branches and became an Army Criminal Investigation Division (CID) special agent serving in several active duty assignments to include Iraq; Afghanistan, and the Pentagon. After twenty-two years of military service, Grogan retired at the rank of Chief Warrant Officer 3.
In his civilian life, at the age of nineteen, Grogan worked as a reserve police officer for the Los Gatos, California, Police Department. At the age of twenty, Grogan spent a thirty-year career with the Millbrae, California, Police Department and retired at the rank of Captain. While at the Millbrae Police Department, Grogan faced two of the greatest tragedies of his life; the murder of a close friend and fellow police officer and the drowning of an infant whom he drove to the hospital, but could not save.