Captain Robert E. Stiles
Deputy, USCG Sector San Juan
Captain Stiles reported to Sector San Juan in June 2024 and serves as the Deputy Commander in support of all Sector missions and forces in Puerto Rico, the U.S. Virgin Islands, and throughout Sector San Juan’s 1.3 million square nautical mile area of responsibility in the Eastern Caribbean. A native New Englander, Captain Stiles is originally from Meriden, Connecticut, and has lived and served throughout the U.S. He joined the Coast Guard in February 2006 via the Direct Commission Lawyer (DCL) program and has held a wide array of legal and operational assignments during his 18 years of Coast Guard service.
Captain Stiles previously served as the Deputy Director of Operations at the Defense Institute of International Legal Studies (DIILS) in Newport, RI, where he supervised the planning, implementation, and assessment of world-wide U.S. legal institutional capacity building (ICB) programs aimed at developing the national security posture of U.S. partner nations. He directly implemented maritime ICB programs in the nations of the Dominican Republic, Palau, Sri Lanka, and Timor Leste. He also oversaw the execution of foreign military training around the globe in Human Rights and the Law of Armed Conflict. A subject matter expert in Military Justice, Maritime Operations and Law Enforcement at Sea, he provided instruction and strategic guidance to military legal practitioners and operators during engagements in 16 key partner nations.
From 2010-13, Captain Stiles served at USCG Sector San Francisco as the Assistant Chief of Logistics. There he qualified and served as search and rescue (SAR) operations unit supervisor. He subsequently served as a senior trial counsel at USCG Pacific Area (2013-15) and was the first Chief of Military Justice & Command Services for the USCG Legal Service Command (2015-16). In 2016, he reported to the Law Division at the Coast Guard Academy (USCGA). As the Law Division Chief, he delivered and oversaw legal instruction and curriculum development at USCGA, including courses in Constitutional Law, Criminal & Military Justice, Maritime Operational Law, International Law, International Humanitarian Law (IHL), and Human Rights Law (HRL).
Captain Stiles is a 1997 graduate of Boston University, where he earned a B.A. in English and B.S. in Education with honors and then began a career as a certified public school teacher. In 2004, he earned a law degree (J.D.) from Northeastern University School of Law in Boston, and in 2021, a Master of Law degree (L.L.M.) from the Army Judge Advocate General’s Legal Center and School (TJAGLCS). He has received numerous personal awards for military service, including the Defense Meritorious Service Medal, USCG Meritorious Service Medal (x2), USCG Commendation Medal (x3), Commandant Letter of Commendation (x2), and he has been recognized for his work by the American Bar Association and the Navy League of the United States.
Captain Stiles is the proud husband of Prof. Elaine B. Stiles, Ph.D., and father of their 16-year-old twins, Madeline and Milo. He is a national level bicycle racer and coach, who also enjoys scuba diving, snow sports, whitewater kayaking, sailing, and traveling with his family.