Debbie Saylor Caldwell

From part-time sports photographer to managing editor, Debbie Saylor Caldwell transformed herself into an award-winning journalist through perseverance and hard work . She is remembered by her friends and colleagues for her tireless dedication following news of her death after a long battle with illness.

Debbie was preceded in death by her late husband Harold Caldwell; parents, Maggie and Levi Saylor, siblings; Gary Webb, Michael Webb, Wilton Harris, Marie Harris and Carole Harris. 

"Debbie was the hardest worker I met in my 30-plus years at the Enterprise," said John Henson, who was the editor of the Enterprise from 1996 to 2011 and a former classmate of Caldwell's at Cawood High School. "She gave me a call one day about working part-time taking football photos, but I had no idea how big a role she would eventually play in the success of our paper. She was never hesitant to take on a challenge and never backed down from a tough story or assignment. She had a voracious desire to learn every part of the business and an innate ability to communicate with everyone."

Debbie worked in several vocations during her career, with her being best known as an award-winning writer, photographer and editor of the Harlan Daily Enterprise, Middlesboro Daily News and Claiborne (TN) Progress.

During her tenure at the Harlan newspaper, she was truly the first to break the news of the Oxycontin crisis unfolding in America. She saw the plague the drug was having on her community and took steps to promote awareness of the dangers and the tragedies unfolding in her hometown. The larger media outlets actually received the credit for her work as they followed her lead to investigate the spread of addiction across the country.

Two other major stories Debbie “covered” were the Paul Browning murder trial and the Darby Coal Mine Disaster.

It is important to note that the work Debbie did was self-taught as she had no formal journalism training. She then taught many others the trade, requiring them to produce accurate articles for her newspapers.

She began as a news and sports photographer and successfully climbed the ladder to the top of the newsroom. She was a photo correspondent for the Associated Press for about 15 years, with her feature and news photos shared around the world and published in newspapers of all sizes. Her sports photography appeared in numerous publications including the cover of the Kentucky Press Association’s magazine. 

She developed many reliable sources for her work by being a trusted and dedicated professional. Often she was asked to assist emergency and other agencies with preparing their press releases for various happenings.

Debbie was a go-to person from the larger media outlets when news happened in Harlan and surrounding counties. They turned to Debbie to learn what was taking place and where they needed to go. She was the media personnel’s tour guide. 

Debbie wasn’t just about the big stories. She was dedicated to helping and serving others. She worked to save a cemetery that was in the line of reconstruction on U.S. 421, demanded caution signs warning motorists of elk and deer crossings, and fought to remedy sliding conditions on U.S. 421 across Pine Mountain. 

She was well known, having made many friends through her work in food service at convenience stores and the Harlan Nursing Home. She served as an assistant to Harlan Circuit Court Judge Ron Johnson for several years.

She loved her Harlan County Rescue Squad family where she volunteered in various compacities, including public information officer.

She loved her police officers of which so many became family to her. She was there for them and they were often there for her. She was proud of her “Behind the Badge” series where she worked to promote the officers and the work they did each day to serve others. 

She was proud of the award she won for the article “Saving Emily.” Emily was a small child who was walking with her mother on U.S. 119 at Varillla Curve when the mother was struck and killed. Debbie showed the human side of the officer who worked this case and recalled how “the trooper cried when I talked to him.”

She had the honor of being granted an interview with Harlan County legend Mag Bailey and a photo shoot. However, by the time Debbie returned to the office, Mag backed out in fear that she might have embarrassed someone she mentioned in the interview or get them into trouble in some way. 

Left to mourn her passing is her husband, Robert Spears; children, Contessa Watkins, Lawrence Brandon Robbins, Christopher Robbins and Sarah Robbins; 10 grandchildren; 1 great-grandchild, siblings; Jerry Saylor, Donnie Saylor, Jimmy Craig, Eli Craig Jr, Brenda Webb, Dalene Webb, Russell Bennett, Tony Harris, Madeline Harris, Ana Harris and Monroe Craig. Many nieces, nephews, family and friends are also left to mourn her passing. 

Visitation will be held in the chapel of Mount Pleasant Funeral Home on Sunday, January 28, 2024 from noon until 8:00 PM. Funeral Services for Debbie will be held on Monday, January 29, 2024 at 1:00 PM in the Chapel with the Reverend Freeman Clark officiating. Interment will follow at Resthaven Cemetery. There will be a memorial dinner at the Harlan Civic Center immediately after the burial, all are welcome to come and share memories of Debbie’s life.

Mount Pleasant Funeral Home is honored to serve the family of Mrs. Debbie Saylor Caldwell.