Sergeant Major Estrella was born in Gary, Indiana, and raised in East Chicago, Indiana. He attended high school in Erie, Pennsylvania from 1998 to 2002. 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 then reported to the School of Infantry, Camp Geiger, North Carolina where he would attain the military occupational specialty of 0311, Infantry Rifleman. Sergeant Major Estrella would then report to 2d Battalion 6th Marine Regiment, 2/6, “The Ready Battalion.” He would immediately serve with the battalion in support of Operation Iraqi Freedom from February 2003 through May 2003 as a Automatic Rifleman. Shortly afterwards Sergeant Major Estrella participated in the Unit Deployment Program to Okinawa, Japan from September 2003 through April 2004 as an Infantry Squad Leader and was meritoriously promoted to Corporal in July 2004.
Sergeant Major Estrella would be given an opportunity to again serve his battalion and 2nd Marine Expeditionary Brigade (2nd MEB) in support of Operation Enduring Freedom from August 2004 through February 2005 in Kabul, Afghanistan. He and his unit deployed to Fallujah, Iraq from August 2005 through April 2006 where 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 would partake in another deployment to Fallujah, Iraq from March 2007 through 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 successful completion of Drill Instructor School Sergeant Major Estrella would serve within the Third Recruit Training Battalion from August 2008 through February 2011. He was promoted to the rank of Staff Sergeant throughout that time period as well. 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 a Chief Drill Instructor in Kilo Company before accepting to serve at Drill Instructor School as the DI School Drill Master from March 2011 through April 2012. After his tour Sergeant Major Estrella then reported to Camp Pendleton, California for assignment with 2d Battalion, 4th Marines, 5th Marine Regiment, 2/4, “The Magnificent Bastards.”
Upon arrival with 2d Battalion 4th Marines Sergeant Major Estrella would deploy to the Republic of Georgia in support of The Georgian Deployment Program to prepare Georgian Infantry Battalions to conduct combat operations within Afghanistan from May 2012 through August 2012. Sergeant Major Estrella deployed to Okinawa, Japan to support the 31st Marine Expeditionary Unit (MEU) from May 2013 through October 2013 as a Platoon Sergeant. Shortly afterwards he participated in Valiant Mark, a bilateral exchange with the Singapore Armed Forces abroad in February 2014. One month later Sergeant Major Estrella was meritoriously promoted to Gunnery Sergeant and served as a Platoon Commander in preparation for the units 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 3 summer cycles at Officer Candidates School in Quantico, Virginia as a Sergeant Instructor and a Company First Sergeant from April 2015 through September 2018. Sergeant Major Estrella was frocked to First Sergeant in May 2018 and would go on to serve within the United States Central Command (USCENTCOM) area of responsibility with Fleet Antiterrorism Security Team Company Central Command (FASTCENT) in Manama, Bahrain from September 2018 through 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 through July 2022. Sergeant Major Estrella assumed his post as the VMFA-323 "Death Rattlers" Squadron Sergeant Major in August 2022. His personal decorations include: Purple Heart, 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.
Sergeant Major Estrella is married to Theresa Estrella and they have 3 children Jr, Ace, and JJ.