The lackluster Democratic campaign to defeat Frederick County’s MAGA sheriff

If there were ever an election for MAGA die-hard and five-term Frederick County Sheriff Chuck Jenkins to lose, this year’s would be the one.

Republicans are underwater across the country thanks to President Trump’s unpopular agenda, from tariffs to war to immigration enforcement. Jenkins, a controversial figure and immigration hardliner, eked out a victory in his last election by fewer than 3,000 votes. And since then, the GOP’s registration deficit in the fast-growing county has increased.

Polls show Democrats nationwide are fired up and ready to send a message. Karl Bickel, their nominee for sheriff in Frederick County? Less so.

“I hate campaigning,” Bickel said. “I am not a good campaigner. I never do enough when it comes to campaigning.”

Bickel, 72, has run against Jenkins on three previous occasions. While he’s gotten closer each time, he’s never been able to get it over the finish line, even when other Democrats, like County Executive Jessica Fitzwater, have won.

Part of Jenkins’ success can be ascribed to his entrenchment in Frederick County politics. Another reason is that Bickel is hardly on the trail. Bickel does little door-knocking and attends few in-person events. He told The Banner he doesn’t like public speaking and prefers small groups. Bickel won a three-way primary in June.

At an October meeting of the South Frederick County Democrats, candidates for county and General Assembly offices were clear about the opportunity offered by this political climate and the need to run through the finish line. They’re knocking on doors, hosting fundraisers, and trying to meet voters wherever they are. Optimism for a local blue wave — some of the legislature’s top Republicans represent Frederick County — was prevalent.

But what about the guy running against Jenkins?

“I’m tired of having the only Karl Bickel sign north of Highway 40,” one attendee, Gary Bauleke, told the crowd of about 30 people. Bickel’s campaign has raised just $13,684 since its inception. As of Oct. 18, it had $6,571 in the bank. He has not purchased any advertisements and does not have a plan to do so.

“I’ve been a public official in Frederick for a decade and I’ve only seen this guy maybe once in person,” said Del. Jesse Pippy, a Republican and chair of the Frederick County legislative caucus. “Even folks on his side of the aisle have said to me privately that they’re not sure he can win.”

It’s not that Bickel doesn’t understand what he’s supposed to campaign on. A mustache-shaped piece of Bickel campaign literature, only a rough approximation of the candidate’s own facial hair, calls Jenkins an “extremist” who bases decisions on “conspiracy theories.” Jenkins has said that the 2020 election was stolen and that his 2023 federal indictment for gun running — the charges were later dismissed — was politically motivated due to his support for Trump.

Bickel even recognizes his biggest asset is that he’s the other guy. His aversion to campaigning may not matter.

“So many times I go out and people are saying, ‘Anybody but Jenkins, anybody but Jenkins.’ Well, it’d be nice to be something other than the anybody but Jenkins because I do bring a lot to the table,” he said.

Jenkins recognizes he’s vulnerable. In an interview, he acknowledged Democrats’ numbers advantage and said the county, once reliably Republican, has become “hard to read.” But unlike his opponent, Jenkins loves campaigning.

His yard signs, more than 3,200 handed out, are everywhere. He is a regular at American Legion halls and ribbon cuttings and cookouts. He can get MAGA stalwarts like Chad Wolf, a former United States secretary of Homeland Security, to fundraise with him.

Jenkins’ campaign has spent eight times as much as Bickel’s has raised, and his ads are on local radio and in the local newspaper.

“I feel, guardedly, good,” he said. “My campaign is boots on the ground. I wear out shoe leather. I’m out in public every day.”

Even their personalities could not be more different. Bickel, a former policy analyst at the Department of Justice, takes an intellectual approach, pointing the public and reporters to white papers he’s written or op-eds in which he lays out his ideas for reforming the sheriff’s office. One local Democratic activist described him as an “introvert.” His campaign’s only messaging tool is a Facebook page that publishes AI-generated content and sees mixed engagement.

Jenkins is a brash good ole boy who’s not afraid to be outspoken on virtually any topic, much like Trump. Once he likened immigrants living in the country illegally to Hamas, saying he believed there were terror cells lying in wait inside the U.S. In an interview earlier this year with Bolts magazine, he called Bickel, who was a sheriff’s office supervisor in the ’90s and oversaw Jenkins, a “treacherous prick.”

“I’m going to tell you what, man to man: I’d kick his ass, personally,” Jenkins told Bolts. “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.”

In his interview with The Banner, he acknowledged he got “carried away” and “probably shouldn’t have” said that. He claimed he was just responding to repeated online attacks by Bickel and that he was sick of personal attacks.

When Bickel posted a section of Jenkins’ fiery quote on his campaign page, many commenters supported Jenkins. But Bickel, who said he doesn’t think Jenkins is “very smart,” said he doesn’t feel similarly violent.

“I feel sorry for Jenkins,” he said.

Local Democratic sentiment is less sympathetic.

Concerns about heightened activity by U.S. Immigration and Customs Enforcement came to a head in September after immigration agents clashed violently with residents in the city of Frederick’s Taskers Chance neighborhood. Some connect the ramp-up directly to Jenkins, who forged a longstanding relationship with the agency.

Tom Homan, Trump’s border czar, is a personal friend of Jenkins. In 2008, Jenkins made the Frederick County Sheriff’s Office one of the first in the country to formally partner with ICE. When the General Assembly outlawed these partnerships earlier this year as a response to ICE activity nationwide, Jenkins warned that it could result in more aggressive enforcement in places like Frederick County.

At the South Frederick Democrats’ meeting, candidates for every office told those in attendance that the best thing they could do for public safety, especially around immigration, was to “vote for Karl.”

In response to Taskers Chance, Bickel recirculated a policy proposal he wrote in January that, in part, calls for sheriff’s deputies to document encounters with ICE agents to see if people’s civil rights were violated and determine whether there could be prosecution as a result.

That response, and much of Bickel’s messaging, is being shaped in part by an analytical model from Wellspring Digital, a Frederick-based digital marketing agency that hasn’t worked in politics previously. Called Strawberry, the model, according to its creator, Wellspring CEO and founder Karl Hindle, captures public sentiment across platforms, crunches voter data and produces simulations of how the election will turn out.

Hindle, who has rebuilt Strawberry four times, said every run shows Bickel will beat Jenkins — the only question is by how much.

“I think he’s going to wipe the floor with Chuck Jenkins,” said Hindle, who is doing the work pro bono. Of course, there’s a world where Strawberry is entirely wrong, which is something Hindle has considered.

“This is going to be a big acid test,” he said.

Bickel touted the analytics at the South Frederick County Democrats meeting but admitted he isn’t entirely certain of Strawberry either. Similarly rosy polls and predictive models showed Democrats with massive advantages before they lost to Trump.

“When I hear the good news, I get nervous,” Bickel said.