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Kentucky by Heart: Little-known story of Tuskeegee Airman who parachuted into Loretta Lynn’s town

By Steve Flairty
NKyTribune columnist

Occasionally, I find an interesting Kentucky story that I’m surprised I hadn’t already heard. I ran across one of them a few days ago. The story deals with a connection between a decorated Tuskegee Airman and the iconic country music singer, Loretta Lynn. The event surrounding the story happened on March 25, 1948, a time when likely those outside the future singing star’s community even knew her.

Stewart’s “Soaring to Glory” book cover

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

Bleeding and hanging two feet from the ground with the parachute holding steady in the top of the tree, he cut himself free to the ground. He removed his official white scarf and used it as a tourniquet to stop bleeding from his wounds. It was still raining, and Stewart positioned himself under a rock overhang.

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

Steve Flairty is a teacher, public speaker and an author of seven books: a biography of Kentucky Afield host Tim Farmer and six in the Kentucky’s Everyday Heroes series, including a kids’ version. Steve’s “Kentucky’s Everyday Heroes #5,” was released in 2019. Steve is a senior correspondent for Kentucky Monthly, a weekly NKyTribune columnist and a former member of the Kentucky Humanities Council Speakers Bureau. Contact him at sflairty2001@yahoo.com or visit his Facebook page, “Kentucky in Common: Word Sketches in Tribute.” (Steve’s photo by Connie McDonald)

According to reports, Loretta’s younger brother, Herman, heard an unusually loud explosion (said to be louder than the typical coal mining blasts in the area) on that early spring day. It’s unclear where Loretta was at that precise moment.

Stewart’s abandoned plane had flown above the Webb family cemetery and crashed into the hilltop overlooking their home, creating a ten to fifteen deep crater. Debris from the plane was scattered all around the crash site. As the story goes, the next few days saw people in the community make use of the P-47 Thunderbolt and its parts and pieces. One report said that one of Loretta’s uncles took the plane’s stainless-steel nuts and converted into finger rings.

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

Lafe then took the pilot to a nearby store, where a pickup truck transferred Stewart to the Paintsville Clinic. There, he was placed in a bed and given a pain reliever — though not the pain reliever Lafe Daniels had given him earlier, namely a shot of moonshine that Stewart mistook for water. Stewart reportedly mentioned later that the moonshine caused him to feel “delirious.”

News of the crash spread quickly in Loretta Webb’s community, and that brought many visitors — likely curiosity seekers — to the clinic to see the pilot who landed unceremoniously in this southeastern Kentucky county. On March 26, an Air Force representative arrived from Columbus, Ohio, to quietly take Stewart away. There was no fanfare at the time of his departure, but some 57 years later, on August 6, 2005, Stewart was given a hero’s welcome at the annual Van Lear’s Town celebration.

Loretta Lynn’s album cover

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

Who knew that 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 his daughter. He is widowed. Loretta Lynn, at 90, released a new album in 2021. She is also widowed. You might say Stewart and Lynn have done quite well in life, and they have literally walked on the same ground.

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

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