Kentucky by Heart: Little Known Story of Tuskeegee Airman Who Parachuted into Town by Loretta Lynn

By Steve Flairty
NKyTribune Columnist

Every once in a while I find an interesting story from Kentucky that I’m surprised I haven’t heard before. I ran into one a few days ago. The story deals with a connection between a decorated Tuskegee Airman and iconic country music singer, Loretta Lynn. The event surrounding the story happened on March 25, 1948, a time when presumably those outside of the future singing star’s community even knew her.

Cover of Stewart’s “Soaring to Glory” book

Captain Harry Stewart, Jr., a decorated fighter pilot and member of the famed African-American air force unit, the Tuskegee Airmen, piloted his P-47 Thunderbolt fighter over the eastern mountains from Kentucky. Stewart was part of a simulated armed reconnaissance formation flying from Greenville, South Carolina to their home base in Columbus, Ohio. Flying at 20,000 feet in a thunderstorm, he encountered severe engine trouble. Fearing crashing into a mountain to his death, he reduced his altitude to 10,000 feet and jumped from the plane. In the process of ejecting from the plane, he fractured his leg but was able to parachute out safely, landing in a dead pine tree.

Bleeding and hanging two feet off the ground with the parachute held firmly to the top of the tree, he cut himself to the ground. He took off his official white scarf and used it as a tourniquet to stop the bleeding from his wounds. It was still raining and Stewart ducked under a rocky overhang.

This is where it gets even more interesting. Stewart had parachuted into the woods of Butcher Hollow, near Van Lear, Johnson County – which happened to be the childhood home of 15-year-old Loretta Webb. Webb would one day be known as country music star Loretta Lynn, aka “Coal Miner’s Daughter.”

Steve Flairty is a teacher, speaker, and author of seven books: a biography of Kentucky Afield host Tim Farmer and six in the Kentucky’s Everyday Heroes series, including a children’s version. Steve’s “Kentucky’s Everyday Heroes #5” was released in 2019. Steve is a senior correspondent for Kentucky Monthly, a weekly columnist for NKyTribune, and a former member of the Kentucky Humanities Council Speakers Bureau. Contact him at [email protected] or visit his Facebook page, “Kentucky in Common: Word Sketches in Tribute.” (Photo of Steve by Connie McDonald)

According to reports, Loretta’s younger brother, Herman, heard an unusually loud explosion (louder than typical coal mine explosions in the area) that day in early spring. Loretta’s whereabouts at this specific time are unknown.

Stewart’s abandoned plane had flown over the Webb family cemetery and crashed into the top of the hill overlooking their home, creating a crater ten to fifteen deep. Debris from the plane was strewn all around the crash site. As the story goes, the following days saw members of the community using the P-47 Thunderbolt and its spare parts. A report said one of Loretta’s uncles took the stainless steel nuts from the plane and turned them into rings.

About five miles in the air, a nine-year-old neighbor of the Webbs saw the parachute with Stewart falling from the sky and thought it was a white eagle. She told her father, Lafe Daniels, and he rode to the site, finding Stewart injured. Daniels secured Stewart on a second horse and brought him home, where Lafe’s wife, Mary, administered the aid.

Lafe then took the pilot to a nearby store, where a van transferred Stewart to the Paintsville clinic. There he was placed in a bed and given painkiller – but not the painkiller Lafe Daniels had given him earlier, namely a shot of moonshine which Stewart mistook for water. Stewart later reportedly mentioned that the moonlight made him feel “delusional”.

News of the accident spread quickly through the community of Loretta Webb, bringing many visitors – probably curious people – to the clinic to see the pilot who landed unceremoniously in this southeastern county. Kentucky. On March 26, an Air Force representative arrived from Columbus, Ohio to quietly take Stewart away. There was no fanfare when he left, but some 57 years later, on August 6, 2005, Stewart was greeted as a hero at Van Lear’s Town’s annual celebration.

Loretta Lynn album cover

“He was the Grand Marshall of the parade, articulate and a really cool guy… snappy and quick,” recalled Lee Mueller, who reported for the Lexington-Herald on Stewart’s return visit to Van Lear. A group from Cincinnati, veteran “Red Tails”, a designated name referring to the Tuskegee Airmen due to the color of their planes, came to the event in support. “There was a huge crowd. I bought T-shirts for me and the parents who accompanied me. I still have mine.

Who knew a celebrity other than Loretta Lynn could be so celebrated in such a small community?

Stewart is still living and is 97, residing in Bloomfield Hills, Michigan, with her daughter. He is a widower. Loretta Lynn, 90, released a new album in 2021. She is also a widow. You could say that Stewart and Lynn did pretty well in life and they literally walked on the same ground.

Sources: African American News and Geneology;; Military Wiki; Appalachian Encyclopedia (The University of Tennessee Press, 2006); Lexington Herald-Leader, July 8, 2005;; conversation with Lee Mueller, former Lex.-Herald reporter, Eastern Kentucky Bureau

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