Wills Celebrates 50 Years At Harbor Towing & Fleeting

Debbie Wills first began helping in the front office at Harbor Towing & Fleeting LLC as a high school student in the early 1970s alongside company founder Gerald D. Clower. On June 1, 1976, Debbie officially began working at the company full-time.

Fifty years later, Wills is still at her desk, serving as Harbor Towing’s office manager.

Over the years, she has watched both the company and the maritime industry change dramatically. Since 1976, Harbor Towing has evolved through three generations of family leadership, embraced successive waves of new technology and rebuilt after Hurricane Katrina destroyed its facilities.

“I went from carbon paper and typewriters to computer screens in front of me, so, I’ve learned a lot,” Wills said. “You’ve got to go with the flow and go with the progress of the company and the industry.”

A Career Anchored In Family

Clower and Wills quickly formed a close bond that extended beyond the workplace. Their relationship became especially meaningful during one of the most important moments of her life.

“He actually gave me away at my wedding because my father had passed away six months before my husband and I were getting married,” Wills said. “I looked up to him as a father figure.”

That sense of family remains central to the company today.

Wills is the sister-in-law of Harbor Towing President Gerald “Jerry” Clower and the aunt of owner and CEO Todd G. Clower. Todd Clower said her decades of experience and institutional knowledge remain among the company’s greatest assets.

“She is an integral part of our success and our longevity,” he said. “People sometimes say, ‘She knows where the bodies are buried,’ but what that really means is that she remembers what we’ve encountered before. We may be dealing with an issue today, and she can tell us that we faced something very similar 20 years ago and explain how it was handled.”

Adapting To A Changing Industry

When Wills began working at Harbor Towing, communication relied on landline phones, handwritten vessel logs and paper invoices on carbon paper.

As new technology became available, Wills often pushed the company to modernize, although convincing G.D. Clower sometimes required persistence.

“I had to fight him to get a push-button phone and a fax machine, and we really had to fight him when we went to our first computer,” she said with a laugh. “Back then, he used to get on the phone to do vessel traffic and write it all down by hand, so he’d be on the phone with customers for an hour.”

Through each transition, Wills adapted alongside the company.

“She’s been on board with every system change,” Todd Clower said. “Things have moved ahead quite quickly, especially over the last 15 years, and she’s stayed on top of all of it.”

One thing that has remained constant is Wills’ close relationship with Harbor Towing’s crews on the river.

“I have great relationships with the guys at the fleet and on the boats,” she said. “The Mississippi River is very unforgiving, especially in high water. Every time I talk to one of them, I always tell them, ‘Be safe out there.’ “

That type of care and concern has earned her the reputation of being a “Mother Hen” among crew members, who know they can reach out to Wills for just about anything.

“It’s not unusual for a deckhand to call her about an insurance issue or a personal situation,” Todd Clower said. “She’s very well connected and very vocal with the crew members, and they get to know her pretty well.”

Looking Ahead

Outside of work, Wills also recently celebrated another 50-year milestone, her wedding anniversary with her husband, Al. Although she joked that their children, Craig and Heather, would like her to continue working, Wills might finally be looking at taking her well-deserved retirement.

“I told Todd I’ll probably retire next year, but I’m going to see how I feel at that point,” she said. “Maybe I’ll just work fewer days, but I haven’t decided yet. I’ve been loyal to them, but they’ve also been very loyal to me.”

Whenever Wills decides to officially retire, her impact and presence will be greatly missed.

“She’s certainly not just an office manager,” Todd Clower said. “She’s integral to the company and everyone in our team. Around here, everyone does a little bit of everything, and she’s always been a part of it all.”

Nowadays, spending five decades with one company has become increasingly rare. When asked what’s kept her at Harbor Towing for so long, Wills’ answer was simple: family.

“Why have I stayed so long? Working for family, and you can quote me on that,” she said. “That is what kept me here.”

Editor’s Note: Chase Pray joined The Waterways Journal for an internship in the summer of 2026. He is a rising junior at the University of Missouri and is pursuing a bachelor’s degree in journalism with an emphasis in reporting and writing. Chase is a state government reporter for the Columbia Missourian and was also the former editor-in-chief of Mizzou’s student newspaper, The Maneater. The Waterways Journal is pleased to be introducing young aspiring writers and editors to the barge industry, and we hope to continue this practice in future summers.

Featured photo caption: Debbie Wills, Harbor Towing & Fleeting’s office manager, works at her desk. Wills began working full-time for Harbor Towing in 1976, and she recently celebrated 50 years of service. (Photo courtesy of Harbor Towing & Fleeting)