JOINT BASE ANDREWS, Md. –
U.S. Air Force Staff Sgt. Jesse Lookingglass, whose roots trace back to the Pine Ridge Indian Reservation in South Dakota, has found a way to honor his heritage while maintaining aircraft readiness for the National Guard.
“My grandmother was born on Pine Ridge,” Lookingglass shared. “She went to college and eventually planted roots in D.C., but our family still returns to South Dakota every year for traditions and ceremonies.” He says he carries a deep connection to his heritage—Staff Sgt. Lookingglass belongs to four different tribes: Lakota, Seneca, Navajo, and Comanche.
For Native American Heritage Month, Staff Sgt. Lookingglass, who works as a crew chief and mechanic within the D.C. Air National Guard's 213th Maintenance Squadron, reflects on the meaning of service, family legacy, and cultural pride.
“Being able to explain my culture, especially during Native American Heritage Month, is important. Many people have limited exposure to Native Americans, and it’s rewarding to answer their questions and share the reality beyond Hollywood stereotypes,” Staff Sgt. Lookingglass said, noting that Lakota traditions often align with popular images of Native life.
In addition to his heritage, Staff Sgt. Lookingglass draws inspiration from his family’s legacy of service. His grandfather, a medic in the Air Force during the Vietnam War, left an indelible mark on the family. “Even though I never met him, continuing that tradition means a lot to me,” he explained.
Staff Sgt. Lookingglass joined the military at a pivotal point in his life. He was expecting his first child and realized he needed a stable source of income to give his unborn daughter everything she would need.
So, after serving as a reservist, he transitioned to National Guard and has since worked full-time as a crew chief, ensuring that military aircrafts, like C-40s— which provide world-class travel for members of the Executive Branch, Congress, Department of Defense, and high-ranking U.S. foreign dignitaries—are well maintained and mission ready.
“On the weekends, I’m a Guardsman, but during the week, I work in a similar role as a federal employee.”
His journey in the Air Force has also taken him overseas. In 2022, he deployed to Al-Udeid Air Base in Qatar, an experience that left a lasting impression. “It was a culture shock—everything was different, from customs to the heat. But it broadened my perspective,” he recalled.
When it comes to his future and his goals, Staff Sgt. Lookingglass said he plans to pursue a commission as an officer while continuing his education at George Mason University, where he is studying physics. “Being enlisted has been an incredible experience, but I’m aiming for the next level of service,” he said.
When asked what Native American Heritage Month means to him, Staff Sgt. Lookingglass said the commemoration offers a chance to remind others of his community’s resilience. “We’re still here—still speaking our languages, holding ceremonies, and living on the same land as our ancestors. It feels meaningful to defend this land, just like they did, but now in service to the United States.”
As he balances his roles as crew chief, student, and family man, Staff Sgt. Lookingglass embodies the spirit of service that unites the past and present—a fitting tribute during Native American Heritage Month.