Caldwell retires after 2 decades

Published 1:44 pm Friday, December 15, 2017

It was a bittersweet event at the Harlan Daily Enterprise as the community dropped by recently to celebrate the retirement of one of its longtime employees.

The afternoon yielded everyone from a local judge to members of the Kentucky State Police Post 10, the Harlan County Sheriff’s Office and the Harlan County Rescue Squad stopping by to relay their good wishes and goodbyes to Regional Editor Debbie Caldwell.

Caldwell, who began her career with the Enterprise in 1995 as a sports photographer climbed her way up the ladder of success for more than two decades to become the regional editor of three local papers, including the Middlesboro Daily News and the Claiborne Progress, as well as the Enterprise.

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Caldwell served as a reporter and photographer for the Enterprise throughout the 1990s and into the 2000s, as well as serving several years in the position of news editor. The later part of her journalism career saw her as managing editor of the Enterprise and then the regional editor of the three papers. This added to her responsibilities of leader and editor of a larger crew of reporters and photographers in which she trained many one-on-one for the general assignment journalism beats.

“My main goal and interest was always the well-being of the paper and making sure all the reporters had their facts right,” said Caldwell. “This is not only to ensure the legalities of the job but to serve the community and to ensure that nothing is wrongly reported.”

Caldwell, who entered the workforce 41 years ago has enjoyed other work, job descriptions, and careers along her road to her newspaper career. These include work as a teenager with a local carpet and steam company as well as selling Grit newspapers, in which she would carry out these duties in the evenings after school and on weekends to earn extra money.

In the 1980s Caldwell began work on a larger scale in food service where she worked for several years in local school cafeterias and managed delis at several Kwik Mart gas stations throughout the area.

In the early 1990s and just prior to beginning her career with the Enterprise she served as the dietary manager of the dietary department of the Harlan Nursing Home.

“I have never been without a job at any time,” said Caldwell. “When I left any job to better myself I always had another one lined up and gave the current one adequate notice. That’s how you do things. When people are good enough to give you work, you always give them enough notice to replace you before leaving. I am also proud to say that I have never been fired from a job.”

Caldwell said she would continue working longer in her current position if not for her failing health due to the serious onset of health issues following a bad fall in October 2016.

“Leaving my job at the paper has been a very hard decision for me, but due to my health, I cannot push myself any longer. I will miss my co-workers and talking to the people who visited my office on a daily basis,” Caldwell said. “I’ve made many friends over the years and I thank them all for the beautiful memories and giving me the opportunity to record the events in our everyday lives.”

Raymond and Donna Cox, among many who attended the celebration on Thursday, said they would forever miss her being at the papers.

“It won’t be the same without her. Seeing her go is a very sad thing to us,” said Donna Cox. “She has always been so good about getting everything in the paper and getting it in there on time.”

Raymond Cox said he remembers teaching Caldwell in elementary school biology and recalls what a wonderful student she was.

“She was always so intelligent and such a great student,” said Raymond Cox who also noted that it had been an honor to watch her grow through her career in journalism.

Caldwell is the mother of four children who reside in Wallins Creek. She resides in Mooresburg, Tennessee, with her husband Bob Spears. She will also spend time in Florida where they are currently building a small winter vacation home.

“Debbie has been a cornerstone of the Harlan Daily Enterprise and our other papers for many years. Her commitment and passion for getting local news to the community is unmatched. We wish her the very best as she enjoys her retirement and will miss her deeply,” said Bill Sharp, group publisher for the three papers.

Marisa Anders, former editor of the Claiborne Progress, who worked under Caldwell’s direction, will be serving as interim regional editor of the three newspapers upon Caldwell’s retirement.

Anders, who has been a journalist for 15 years and has extensive experience in the public relations and marketing fields, says it will be a challenge, but one she is ready to take on.

“I thank Debbie for her years of leadership and wish her nothing but the best in her retirement,” Anders said. “She will be very missed. I look forward to being part of each community.”

Anders may be reached at