Tipsword to run for Woodford Sheriff
- Kent Casson
- Jul 29
- 2 min read
With the surprise decision by Woodford County Sheriff Matt Smith not to seek re-election in 2026, Dennis Tipsword is announcing he will run for sheriff in 2026, no longer seeing re-election as a state representative.
Tipsword currently serves simultaneously as State Representative for the 105th District and Chief Deputy Sheriff of Woodford County.
Tipsword is expected to serve out the remainder of his current term as State Representative. He had previously announced he would seek re-election as State Representative but that was based on his belief that current Woodford County Sheriff Matt Smith would seek re-election in 2026. Tipsword and Sheriff Matt Smith are both Republicans.
“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,” said Tipsword. “While it has been a high honor to serve the people of the 105th District in every way, my heart is in law enforcement and with Sheriff Smith’s decision not to seek re-election, I am compelled to step up to run for Woodford County Sheriff next year.”
Tipsword has been in law enforcement for 31 years and been with the Woodford County Sheriff’s Office for 18 of those years while serving as Chief Deputy Sheriff for the past 11.
Tipsword has a B.S. Degree in Law Enforcement Administration from Western Illinois University. He is also a graduate of the Police Training Institute of the University of Illinois, and a graduate of the School of Police Staff and Command from Northwestern University. He has also served as an undercover officer for the Multi County Narcotics Enforcement Group for Woodford, Peoria, Tazewell and Knox Counties.
Dennis and his wife Betsy have three grown children and eight grandchildren with one more on the way. They all live in Woodford County where Dennis was born and raised himself.
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