Sergeant Major Estrella is a native of Gary, Indiana. He enlisted in the Marine Corps in July 2002 and was introduced to the recruit training process at Marine Corps Recruit Depot, Parris Island, South Carolina. Upon completion of Recruit Training, Sergeant Major Estrella reported to the School of Infantry, Camp Geiger, North Carolina, where he attained the military occupational specialty of 0311, Infantry Rifleman. He then reported to 2d Battalion, 6th Marine Regiment and immediately served with the battalion in support of Operation Iraqi Freedom from February 2003 to May 2003 as an Automatic Rifleman. Shortly afterwards, Sergeant Major Estrella participated in the Unit Deployment Program to Okinawa, Japan from September 2003 to April 2004 as an Infantry Squad Leader. He was meritoriously promoted to Corporal in July 2004.
Sergeant Major Estrella was given an opportunity to again serve his battalion and 2nd Marine Expeditionary Brigade in support of Operation Enduring Freedom from August 2004 to February 2005 in Kabul, Afghanistan. He was deployed to Fallujah, Iraq, from August 2005 to April 2006. In November, he was meritoriously promoted to Sergeant and medically evacuated to the United States from wounds suffered in combat. Once recovered, Sergeant Major Estrella deployed to Fallujah, Iraq, from March 2007 to October 2007. After completing his final deployment with the unit, he received orders to attend Drill Instructor School aboard Parris Island, South Carolina, in April 2008 as a student.
After completion of Drill Instructor School, Sergeant Major Estrella served with the Third Recruit Training Battalion from August 2008 to February 2011. He was promoted to the rank of Staff Sergeant during that time. Sergeant Major Estrella served two companies within Third Recruit Training Battalion, as a Drill Instructor, Experienced Drill Instructor, and Senior Drill Instructor with Mike Company. He served as Chief Drill Instructor in Kilo Company before serving at Drill Instructor School as the DI School Drill Master from March 2011 to April 2012. After his tour, Sergeant Major Estrella reported to Camp Pendleton, California, for assignment with 2d Battalion, 4th Marines, 5th Marine Regiment.
Upon arrival with 2d Battalion, 4th Marines, Sergeant Major Estrella deployed to the Republic of Georgia in support of The Georgian Deployment Program from May 2012 to August 2012. Sergeant Major Estrella next deployed to Okinawa, Japan, to support the 31st Marine Expeditionary Unit (MEU) from May 2013 to October 2013 as Platoon Sergeant. Shortly afterwards, he participated in Valiant Mark, a bilateral exchange with the Singapore Armed Forces, in February 2014. One month later, he was meritoriously promoted to Gunnery Sergeant and served as a Platoon Commander in preparation for the unit’s second 31st MEU deployment from November 2014 through April 2015. Before departing 2d Battalion, 4th Marines, he received orders to The Pennsylvania State University to serve as the Assistant Marine Officer Instructor (AMOI).
While serving as the AMOI for Penn State, Sergeant Major Estrella augmented three summer cycles at Officer Candidates School in Quantico, Virginia, as a Sergeant Instructor and a Company First Sergeant from April 2015 to September 2018. He was frocked to First Sergeant in May 2018 and would go on to serve within the United States Central Command area of responsibility with Fleet Antiterrorism Security Team Company Central Command in Manama, Bahrain from September 2018 to October 2019. He then executed a PCS opportunity to serve at Golf Battery, 3d Battalion, 14th Marines, 4th Marine Division, as the Inspector-Instructor First Sergeant from November 2019 to July 2022. Sergeant Major Estrella next served as the VMFA-323 "Death Rattlers" Squadron Sergeant Major from August 2022 to July 2025 aboard Marine Corps Air Station Miramar.
He is currently serving as the Headquarters Battalion Sergeant Major for Marine Air Ground Task Force Training Command, Marine Corps Air Ground Combat Center, Twentynine Palms.
His personal decorations include Purple Heart, Meritorious Service Medal, Navy and Marine Corps Commendation Medal with gold star in lieu of fifth award, Navy and Marine Corps Achievement Medal with gold star in lieu of fourth award (with combat distinguishing device), and Military Outstanding Volunteer Service Medal.