Enterprise says goodbye to Caldwell

From my seat at the Harlan Daily Enterprise over parts of four decades, I’ve been fortunate enough to work with several outstanding journalists.

When I started my career here, there was no shortage of people to learn from, beginning with the man who hired me. Ewell Balltrip was very likely the best all-around journalist to work at the Enterprise during my lifetime and led a newsroom in the mid 1980s that also included two other local legends in Hoss Davis and Ed Gibson. Jeff Phillips was much closer to my age but had been in the business for a couple of years when I got here and provided the most day-to-day assistance as a reporter in the early days.

One of my jobs for over a decade was hiring reporters and there were many who came through the doors to try a job that is much more difficult than most probably imagine. It’s not physically taxing, but the hours and pressure can be overwhelming.

Debbie Caldwell was one of those aspiring reporters/photographers who called one day and said she wanted to turn her growing love of photography into a part-time job. Debbie and I knew each other from high school, but I hadn’t talked to her in years when she showed up in my office one day. She was up for photographing football games and I sent her out to Cawood High School for a game that Friday night. From my spot in the press box, I remember seeing a photographer caught in the path of a Prestonsburg running back and a couple of Cawood defenders and taking perhaps the hardest hit of the night when they all tumbled out of bounds.

I got a call a little later from Debbie to tell me she had suffered a broken arm in the collision, but she promised she’d be back when she recovered. I didn’t think if I’d ever hear her from again, but that wasn’t the last time Debbie proved me wrong over a 22-year career at the Enterprise that came to a close Thursday.

While I was away at college learning journalism and having a pretty good time, Debbie was home working and raising a family. She had to overcome adversity as a teenager and young adult and was never afraid of hard work or accepting a difficult challenge. She learned journalism by practicing it day after day after day, first in photography and then as a writer. Debbie took on every assignment and learned from her mistakes as we went over her stories in my office each day. I doubted we’d ever find as good a police/court reporter as Lisa Carnahan, but Debbie soon became one of the best in this part of the state while also developing into a tremendous photographer in the days when we already had a ridiculously good group of photographers led by Chris Jones, Jeff Drummond and Russell Burkhart.

There were quite a few days when Debbie would produce photos of University of Kentucky and high school games for the sports page while writing enough stories to fill the entire front page. She never worried about hours or schedules, just getting the story and photo and making our paper the best it could be.

She was always great with people and soon developed many sources who trusted her with sometimes delicate information. For members of the Enterprise staff, she was at times a doctor and counselor who always seemed to know the right answer and could get her point across in humorous ways that made everyone comfortable.

She eventually became our news editor and then succeeded me as managing editor while also leading the Middlesboro and Claiborne, Tenn., papers as regional editor. Health issues started to mount, but Debbie continued to push forward until she finally decided it was best for her to finally start taking care of herself and retire. She plans to move to Florida where she and her husband are building a home.

It’s hard to believe Debbie won’t be in the office in the weeks and years to come. It’s hard for me to remember a time she wasn’t. You can be sure that both Harlan County and the Enterprise will miss her.