Woodford County Sheriff Matt Smith to retire, endorses Chief Deputy Tipsword

In a news release, Matt Smith said “it has been my great honor and privilege to serve three terms as Sheriff of Woodford County,” and the decision not to run has been hard.

“I have developed so many friendships as well as professional and community partnerships. I will continue to work hard as your Sheriff, the remainder of my term for the people of Woodford County,” he said. “Thank you to my wife and family for standing by me through it all. And thank you to the great people of Woodford County for the opportunity to serve as your Sheriff.”

Smith started working for the sheriff’s office in 1984 as a part-time dispatcher. Over the years, he said, he’s moved around within the office, on both the patrol side and the corrections side. He’s been an operations captain and chief deputy before winning his first election as sheriff in 2024.

To replace him, he endorsed Chief Deputy Dennis Tipsword to take over, saying he’s “most qualified and an outstanding choice for your next Sheriff.”

Tipsword has indicated he’ll run in the 2026 election as a sheriff and not as a state representative for the 105th district, which includes Woodford County. He’s been in law enforcement for about 31 years and has been with the sheriff’s office for 18 years, with 11 of those being as the chief deputy.

“I am fulfilled that I have injected a lot more insight regarding law enforcement issues into the House of Representatives in Springfield during my service there, particularly regarding the real world consequences of the SAFE T ACT which passed into law just before I became a State Representative,” he said.

Tipsword is married and has three grown children, all of whom live within the county.

Smith has said he will finish out his term in office as well as Tipsword.