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Home Obituary

Former sheriff Clary dies

Vince Tweddell by Vince Tweddell
December 2, 2025
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Former sheriff Clary dies

Dennis Clary (From Tomblinson Funeral Home website)

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Former Henderson County Sheriff Dennis Clary was the right sheriff at the right time and moved the department forward, say former colleagues and associates.

Clary died Saturday at Deaconess Henderson Hospital. He was 86.

Bill Mills worked for Clary for 10 years and credits him with helping him reach success in his career. Soon after Mills started working at the sheriff’s office, he began working on drug cases, which led to working alongside the federal Drug Enforcement Administration,  the Bureau of Alcohol, Tobacco, Firearms and Explosivesand the Pennyrile Narcotics Task Force, an agency he later joined after retiring from the sheriff’s office.

“He helped me kind of get things going,” Mills said. “My success started out with him.”

Mills said Clary pushed for his sheriff’s office to reach out and work with other law enforcement agencies, as evidenced by the number he teamed up with.

And Mills said Clary moved the local sheriff’s office out of an old style of doing things and into a more modern, professional form of law enforcement.

“He kept things more consistent, more professional,” Mills said. “He was very professional about our deputies, how we worked and what we did.”

Former Henderson County Sheriff and Henderson Police Chief Ed Brady said
Clary was always easy to work with and a great communicator.

But it wasn’t the communication of making a lot of speeches, Brady said. Clary’s strength was in meeting with people one-on-one and hearing their problems and then looking for solutions, Brady said.

It must have resounded with Henderson County residents, Brady said, because the people kept re-electing him.

He was likeable, down-to-earth and people felt like he could be trusted, Brady said.

“He was the right sheriff at the right time,” Brady said.

Clary served as sheriff from 1986 to 2006. In the 2006 election, Brady defeated him and took over the next year.

He said it wasn’t a contentious campaign and the two remained friends after the election. Brady said he’d stop in at Clary’s house from time to time when he was sheriff to check in on him.

Keith Berry, now a magistrate on the Henderson County Fiscal Court, worked as a deputy under Clary for numerous years.

He said Clary hired him in 1993 and he was able to move up in Clary’s tenure. Berry said Clary was a good politician and a good communicator with his constituents.

“I was with him a long time,” Berry said.

Mills said he was able to visit Clary a couple days before his passing and thanked him for helping him in his career.

“He’s one of the better sheriffs they’ve had,” Mills said. “We’ll miss him. His family is going to miss him.”

Read Clary’s obituary here.

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Vince Tweddell

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Vince Tweddell is the founder, publisher and editor of the Hendersonian.

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