In 1988, Monteagudo received his commission through the Air Force Reserve Officer Training Corps at the University of Florida, where he earned a Bachelor of Science in Nuclear Engineering. He also holds a Master’s Degree in Business Administration from the Kellogg School of Management, Northwestern University, Evanston, Illinois, and has attended the Joint Air and Space Operations Senior Staff Course.
Monteagudo earned his wings in 1989, and completed F-16 pilot training in 1990. He completed tours with the 308th Tactical Fighter Squadron, Homestead AFB, Florida; the 68th Fighter Squadron, Moody AFB, Georgia; the 162nd Fighter Squadron, Arizona National Guard, Tucson, Arizona; and the 93rd Fighter Squadron, Homestead, ARB, Florida.
Monteagudo commanded the 93rd Fighter Squadron, Homestead, ARB, Florida, from 2005-2008. From 2008-2010 he was the Deputy Commander, 482nd Operations Group, Homestead ARB, Florida, and was the Vice Commander, 482nd Fighter Wing, Homestead ARB, Florida, from 2010-2011. He was the Commander of the 944th Fighter Wing, Luke AFB, Arizona from 2011-2013.
In 2013 he served as the Mobilization Assistant to the Director of Plans and Programs (A5), Headquarters Air Combat Command, Joint Base Langley-Eustis, VA. In September 2013, he reported to United States Southern Command as the Deputy Director of Operations (J3), Miami, Florida. He assumed command of Joint Task Force Guantanamo on July 1, 2015.
Monteagudo is a command pilot with over 3,700 F-16 hours and over 4,000 total flight hours. He has over 380 combat hours and 130 combat missions. He has received the Legion of Merit, the Meritorious Service Medal with three oak clusters, and numerous other individual and unit awards.