“What do you get when you drop a piano down a mine shaft?” Jerry Gillespie asks.
“What?” you say.
“A-flat miner,” he responds.
If you don’t laugh, that’s okay. Gillespie will just tell you another joke. He has at least one for every occasion: get-togethers of retired U.S. Air Force pilots, church meetings, vacation lunches and flights to take people for medical help.
Gillespie has been a pilot since 1975 and a jokester even longer. He grew up on a Nebraska farm and joined ROTC while attending Kansas State University. He graduated with degrees in engineering and physics and a desire to fly for his country.
Fighter pilot slots were hard to come by after the end of the Vietnam War, but Gillespie snagged one, flying fighters and serving as an instructor pilot. He ended up in Wichita as a member of the Kansas Air National Guard flying F-16 Fighting Falcons.

Jerry Gillespie flew Payton Barnes and her mother, Krista Jamieson, to Colorado for treatment Barnes couldn’t receive in rural Kansas. To see more about Gillespie and one of the patients he has flown, visit Angel Flight Central’s YouTube channel and search for “A small plane and a big heart: Dawson’s Angel Flight Central story.”
Gillespie retired in 1994 and spent two years being “Mr. Mom” to his sons, Jered and Conor, before going back to work as a systems engineer for Boeing, Learjet, Bombardier and Spirit AeroSystems.
He bought his first plane, a Cessna 182, in 1987 and sold it three years later. A decade later, he took the plunge again, buying a Mooney/M20 Series 4-seater single engine aircraft.
“It’s the safest general aviation airplane out there, I was told,” Gillespie said.
After a career flying jet fighters, some might think flying a Mooney would be boring. Many retired Air Force pilots opt for jobs with the airlines flying big planes. But the Mooney was perfect for the next stage of Gillespie’s aviation career.
In 2012, Gillespie joined Angel Flight Central, a Kansas City-based nonprofit that flies people to medical appointments and for other humanitarian purposes. At last count, Gillespie had almost 100 Angel Flight missions to his credit. He flies at least once a month in a 10-state area.
“We use volunteer pilots with their own planes to fly patients to appointments for chemotherapy, radiation, clinical trials and other medical or humanitarian reasons,” said Jenna Gerdes, Angel Flight’s outreach director and development coordinator. “It’s always free to passengers, no matter how many times they go.”
“The best thing about Jerry,” Gerdes added, “is he starts every ride with a joke.”
Gillespie’s jokes break the ice and help make his passengers comfortable with flying in a small plane. And they give Gillespie an opportunity to get to know the people he serves. When there’s room, Gillespie’s wife, Rebecca, goes along.
“(Flying for AFC) makes him very happy,” she said.
“They both get involved in the life of the passenger,” Gerdes said. “Once (they) fly someone they tend to develop a relationship with the passenger.” Rebecca often makes cookies for them.
One of 350 pilots who donate their time to Angel Flight Central, Gillespie was surprised to be honored as its 2024 Volunteer Pilot of the Year at an awards gala.
Gerdes called Gillespie’s mission count “a lot. The highest flyer sits at 300. Gillespie is in the top 10 percent.”
Along with a plaque, Gillespie was presented with a book, “100 Dad Jokes.” Seems like everyone knows his reputation.
“I think,” Gerdes said, “he’s just so compassionate and willing to give — to say yes to a stranger. He takes things to a whole other level.”
Contact Beth Bower at goodlifeguy.com.
No ‘catch’ involved in Angel Flights
For more than 30 years, Angel Flight Central volunteer pilots and supporters have provided free flights throughout the Midwest for families who need access to specialized health care, camps for special needs, disaster response efforts and other compassionate reasons.
The organization serves Missouri, Kansas, Iowa, Nebraska, North Dakota, South Dakota, Wisconsin, Minnesota, Illinois and Indiana. In a partnership with Southwest Airlines, it also offers free flights to patients needing care outside of the 10-state area.
Jenna Gerdes, the nonprofit’s outreach director and development coordinator, said people often wrongly assume there is some “catch” involved. She urged people in need to call Angel Flight Central toll-free at 866-569-9496 or visit its website, angelflightcentral.org, for more information.
The organization is always looking for volunteer pilots and donations to support its efforts.









