Welcome to the Civil Air Patrol America 250 series. We will be highlighting American hero members and their service in this series leading up to the America 250 celebration. This is the second of that series: Lt. Col. Jason Smallfield. If you missed Oregon Wing's Thomas Flaherty Sr., you can read his story here.
Maj. Gen. Stephen Danner (left), then the Missouri National Guard adjutant general, welcomes U.S. Army Col. Jason Smallfield as the command’s inspector general during a 2019 ceremony at the Ike Skelton Training Site in Jefferson City.
Growing up in the small farming town of Pipestone, Minnesota, where his family raised corn, beans, cattle, pigs, and other crops, Jason Smallfield was part of a high school graduating class of 92 students.
In the Pipestone cemetery, he can pay respects to one set of great-great grandparents, all four sets of great grandparents, and both sets of grandparents — all resting in peace.
Pipestone is, in his words, ‘typical small-town rural middle America, where everybody pretty much knows everything” about everyone else in town.
And that cemetery, he said, “is an indicator of small-town life.”
‘Figure It Out’
Three things Smallfield knew.
“One, Farming didn’t really float my boat,” he said. “Two, I wanted to see the world.”
And three, he wanted to go to college, but as on most small family farms, money was tight. Paying for college was a non-starter.
His parents’ advice?
“Figure it out.”
He did, earning a coveted appointment to the U.S. Military Academy at West Point, New York. It was the start of a nearly 35-year active-duty military career where he indeed saw the world, including combat tours in Iraq, Kuwait, and two tours in Afghanistan.
Seeing the World Through Combat
In one of those Afghanistan deployments in the troop surge between 2007 and 2008, a scheduled 12-month deployment became a 16-month tour in the eastern region of the country, where coalition troops faced a heavy Taliban presence.
He also served in Panama, South Korea, and Haiti. An Army Ranger, Smallfield is Air Assault and Senior Paratrooper qualified. He is credited with 41 military jumps. In Haiti, he served as aide de camp to Gen. Philip Anderson, the number two general in a multinational force.
The Haiti deployment offered a surprise.
“The thing that surprised me most is that the accounts from the 1700-1800s describe [Haiti] as a tropical paradise. What was surprising was near Port au Prince on the west central side of the island was the deforestation. It just looked like a desert. Having grown up on a farm, I’d never seen starving critters before. But we saw horses and cattle where you could count the ribs. It was an indicator of the poverty there.
Before his retirement, U.S. Army Col. Jason Smallfield tours Whiteman Air Force Base in 2019 as the Missouri National Guard inspector general.
A Decorated Career in the Army
Smallfield ascended to the rank of colonel before retiring.
He was highly decorated, receiving the Legion of Merit, the Bronze Star, eight Meritorious Service Medals, six Army Commendation Medals, and other honors.
And while he didn’t follow generations of his family to farming, he’s been planting seeds in the lives of Civil Air Patrol cadets, helping them figure it out, while setting an example of service.
He serves as a lieutenant colonel in Civil Air Patrol’s Missouri Wing.
Was there one thing he learned at West Point that he carries through each day? Smallfield was part of the 30-member Golden Knights skydiving team at the academy. There, he learned lessons from coaches and teammates, wisdom he’s applied in Civil Air Patrol.
CAP Lt. Col. Jason Smallfield serves as the incident commander at a Missouri Wing Group 3 exercise, held in May at the Sedalia (Mo.) Regional Airport.
‘Attention to Detail’ Matters Most
“Most of the things I’ve carried through my career I learned from that team. Preparation. Execution. Attention to detail. I’ve got 510 skydives, 41 military jumps. Knock on wood. I’ve never had a serious injury. Part of that is luck and part of that is the attention to detail and the things that I learned from my coaches.”
There are rules that the West Point team lived by, Smallfield said.
“If conditions aren’t safe, don’t jump,” he said. “It’s better to avoid a bad situation than have to be in a position to get out of a bad situation.”
Smallfield — who as a kid had to figure out how to pay for college — earned three master’s degrees beyond his academy diploma.
Then-U.S. Army Capt. Jason Smallfield and his wife, Army Spc. Pamela Smallfield, in uniform at Fort Leonard Wood, Missouri, in 1997.
Setting an Example of Service
In CAP, Smallfield has set an example of servant leadership and seems as busy as he was in his Army days. A member of the Lake Ozark Composite Squadron, [where he served as commander from 2020-2025], he’s currently handling 31 duty assignments for his squadron, group, and wing, notably in emergency services.
He first learned about CAP at a Joint Base Anacostia Bolling presentation by the U.S. Air Force auxiliary while representing the Defense Intelligence Agency. At first, it was a learning opportunity and a chance to serve. But it evolved into something more.
“You stick with it and then you get to move into coaching and mentoring others,” he said.
With characteristic humility, Smallfield downplayed the number of duty assignments.
“From that perspective, it was a small unit that I commanded with about 35 people,” he said.
‘A Consummate Professional’
Missouri Wing Commander Col. Michael Toedebusch, however, had high praise for Smallfield, who serves as a deputy group commander. Toedebusch called him, “a consummate professional.”
“The area that [Lt. Col. Smallfield] has been most influential in is in the establishment of SOPs [standard operating procedures] for wing positions. This was borne out of his Army background and seeing a need for it to improve workflow and continuity.”
Toedebusch credited Smallfield with helping give the Missouri Wing its emergency services identity.
“Given his planning skills, he now works as the primary architect for the [operations] for training and developing a cohesive ‘battle rhythm’ at the local, group, and wing level.”
The Smallfield family poses for a photo in Washington, D.C., in 2018. Standing, from left, are mother Pam Smallfield, and daughters Jessica and Jamie, Seated is the father, U.S. Army Col. Jason Smallfield.
A Chance to Give Back
After nearly 35 years in the active-duty military some might spend their time on the golf course, or on the beach, or on a trout stream. Smallfield continues to serve. Why? Part of the reason is a chance to mentor CAP cadets and younger members.
“Number one, it’s fun. It’s kind of energizing working with kids, working with young adults, that type thing. What I noticed in my family and with people in general, is being retired is one thing. Everybody needs a purpose in life. When they lose that purpose they kind of die out quick has been my observation.”
He added, “Look at Supreme Court justices, physically they may not be able to do what they did in their 20s, but mentally they’re still all there and they still can be value added, finding purpose for themselves and contributing to society overall and that’s kind of what I’m doing.”
A Lesson from Dad, and Others
Smallfield now tries to mentor cadets and newer members, just as he was by his dad, a retired National Guard staff sergeant, his brothers, his coaches at West Point and others. He remembers one bit of wisdom from his dad specifically.
“He said, ‘When you’re an E-1 through E4 you’re learning your job. When you’re a sergeant, you’re training E-1 through E4s. When you’re a staff sergeant, you’re training sergeants. Sergeants first class, they train lieutenants. First sergeants train captains. Maybe, just maybe, when you’re a lieutenant colonel, your command sergeant major won’t have to train you. Listen to your NCOs.’”
Lt. Col. Jason Smallfield (center) provides CAP cadets with a UH-1H operations and safety briefing at the Show Me State Airshow in 2025.
Cultivation of a Different Type
When Smallfield evaluates the crop of CAP cadets, he recalled returning to Pipestone as a newly commissioned officer, ready to talk to teens about the military and the service academies.
“I ended up not doing that, because the kids were pissing me off. I got turned off because there was [in them] a lack of motivation, lack of interest,” he said. “The thing I like about CAP cadets, they kind of self-selected themselves from among their peers. They have the motivation. They have the interest. I’m trying to set them up for success in life, not necessarily success in the military. And there’s a difference.”
For Smallfield, the kid who wanted to get off the farm, he’s doing a different kind of cultivation in the hearts and minds of CAP cadets.
“It’s kind of like farming and planting seeds. I’m doing a different type of farming than my ancestors did. No one understands what I’m saying now, but they listen. And in a couple of years, they’ll say, ‘I didn’t understand it then, but I get it now.’”
Opportunities to Lead Abound in CAP
Civil Air Patrol’s adult ranks consist of volunteers from all backgrounds, including service in the military, like Lt. Col. Smallfield.
CAP, the official civilian auxiliary of the U.S. Air Force, offers hands-on training, mentorship, and service opportunities nationwide.
To learn more about membership and find your local unit, visit gocivilairpatrol.com.
