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USO Guardsman of the Year highlighted for ‘decisive leadership’

Paul Davis
by Paul Davis
April 16, 2026
Master Sgt. Jon Osterhout

Master Sgt. Jon Osterhout

The USO is honoring a member of the Colorado Air National Guard “whose exceptional courage and dedication went beyond the call to duty.”

Master Sgt. Jon Osterhout, who serves with the 140th Aircraft Maintenance Squadron, is among the group of 2026 USO Service Members of the Year named in March.

“The USO Service Members of the Year have shown remarkable commitment to protecting and serving others, often stepping in during critical moments for both fellow troops and civilians,” said USO CEO retired Lt. Gen. Michael Linnington. “These awards highlight the incredible people who serve in our nation’s military.”

Each honoree was nominated by their leadership command with the final selections made by a USO committee. Among Osterhout’s career highlights, according to the USO, is that he “voluntarily accepted a high-risk, short-notice deployment to Prince Sultan Air Base, Saudi Arabia, during an escalating regional crisis in 2025.” 

“Upon arrival in the Middle East, he immediately assumed leadership of a 585-member aircraft maintenance team operating under constant threat of hostile missile fire,” the USO noted.“His decisive leadership drove 14,500 maintenance actions, enabling 2,500 combat sorties that resulted in 29 aerial victories and the use of 671 guided munitions.”

“To me, this award means that I was part of an awesome team that went down range and executed the commanders’ intent at a very high level,” Osterhout said. “In my honest opinion, this award belongs to all 585 people that were part of my team. I am extremely humbled and honored to be recognized by the USO as an outstanding service member and I accept this award on behalf of the folks that it was my privilege to lead.”

Osterhout began his military service as a Marine, where he served as an aircraft mechanic on F-18 Hornets. After his time in the Marine Corps, he returned home to Colorado, and wanting to continue his military service, he joined the Colorado Air National Guard.

Osterhout returned home to Colorado after serving in the Marines and enlisted in the Air Guard.

During his 16 years in the Air National Guard, he has deployed to Djibouti, Africa; Korea; Okinawa, Japan; Afghanistan and Saudi Arabia. Then, in 2024, his squadron was activated for Operation Noble Eagle, the military’s homeland defense mission that began after the attacks of Sept. 11, according to the National Guard Bureau. A year later, the Colorado-native volunteered to go back to Saudi Arabia — noting that because of his own experience as a military kid, he wanted to step up so others with families didn’t have to.

“My unit was given approximately three weeks’ notice to provide an E7 in my AFSC for deployment to the CENTCOM AOR,” Osterhout explained. “I truly felt that I was the best candidate to make the trip. We had just returned from activation for Operation Noble Eagle in late summer of 2024. As the only E-7 without any major family commitments or significant life events happening, I felt it was the right thing for me to do to step up and go on the deployment. When I was a youngster, my father deployed a lot, and I remember how hard it was on my mother, my brother, and myself when my father would have to do two deployments in two years.”

The USO further explained that the actions of Osterhout and his team during this deployment “degraded enemy capabilities, contributing to an 87% reduction in regional missile attacks.”

“My maintenance team supported multiple aircraft types: The largest part of our force was F-16s. We also supported KC-135s, C-130s, E-3s, MH-60s, MH-47s, P-8s, E-2s and various other aircraft types that were at our base for transient purposes. It was definitely a career highlight to be involved with the maintenance on such a variety of aircraft while leading a joint service team.”

He also simultaneously led the Emergency Management Program, safeguarding more than 600 personnel, while directing 27 critical repairs across 13 shelters during five missile alarms.

“Fortunately, my civilian job equipped me with a lot of professional tools, such as coordinating workflow between different agencies, managing contracts and communicating with various stakeholders to achieve the desired outcome in a timely manner,” Osterhout said. “I was able to put these skills learned in the civilian sector to use in a military context.

“I truly believe one of the greatest strengths of the National Guard is the ability that the guardsmen bring from their civilian life and careers coupled with their military training and experience. I believe this is the secret sauce that makes the National Guard something special within the profession of arms. When it comes to leadership skills, I always remember two leadership principles that I learned when I was a young Marine: to know myself and to seek self- improvement, and to know my troops and to look out for their welfare.”

Master Sgt. Jon Osterhout, who serves with the 140th Aircraft Maintenance Squadron, is among the group of 2026 USO Service Members of the Year named in March.

Osterhout said his most difficult task was learning a new job that he had never performed before while in a deployed environment, leading airmen that he had never led before.

As if he wasn’t busy enough, the USO stated that he also volunteered as an instructor for the Joint Top Three Airpower Leadership Academy and mentored 16 NCOs in leadership.

“I believe that one of the major responsibilities that one owes to the profession of arms is to pass on hard earned lessons learned, and to leave the service better than one found it,” Osterhout explained. “I’m getting to the point in my career where one of the most important things I can do is pass on the lessons that I have learned over my 22 years in uniform to the generation that is replacing my generation at a somewhat alarming rate.

“It seems that my generation has been around for quite some time, and it is starting to take its toll. Fortunately, I had the opportunity to help the next generation of leadership and that’s an opportunity that’s too good to pass up regardless of time and location.”

Osterhout and the other six service members will be officially honored at the annual USO Gala, on April 16 at The Anthem in Washington, D.C.

Other honorees include:

Army Capt. Emily Malcom

Marine Lance Cpl. Matthew Garcia

Navy Chief Petty Officer Joseph Hawthorne

Air Force Staff Sgt. Theodore Dudley

Space Force Master Sgt. David Gudgeon

Coast Guard Petty Officer 2nd Class Cody Dmochowski

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Tags: 140th Aircraft Maintenance SquadronCENTCOMColorado Air National GuardF-18 HornetsfeaturedGuardsman of the YearLt. Gen. Michael LinningtonMarine CorpsMaster Sgt. Jon OsterhoutUSOUSO Service Members of the Year
Paul Davis

Paul Davis

Paul Davis is a Navy veteran who served on the USS Kitty Hawk during the Vietnam War. After four years in the Navy, he then worked for 33 years as a DOD civilian. Today, he writes a weekly crime beat column for PhillyDaily.com.

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