For the first time in two decades, Frederick County will have a new sheriff.

Republican Chuck Jenkins, known for his vigorous campaigning and brash public image, had cruised to victory in election after election, even as Frederick County turned increasingly blue.

His Democratic opponent, Karl Bickel, known as a bookish introvert, has described himself as a poor campaigner, saying “I hate campaigning.” Jenkins had already beaten Bickel in three prior elections.

Yet on Tuesday, amid an anti-Trump wave and increasing frustration with their MAGA sheriff, Frederick County voters picked Bickel.

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Jenkins, an immigration hardliner, was indicted on federal charges in 2023 that he helped a gun dealer illegally acquire machine guns. The case was dropped in November 2024, right after Trump’s second presidential victory. Jenkins believed his prosecution was politically motivated.

His loss Tuesday night marked the end of an era in Frederick County, and it was a stark reversal of a prediction Jenkins made earlier this fall.

“I’m going to tell you what, man to man: I’d kick his ass, personally,” Jenkins told the publication Bolts in September. “Someday, he’s got an ass-kicking coming. I don’t like the son of a bitch. Personally, politically, he’s no good. He can read all the books he wants.”