He may be the best-known man in Frederick County.
Chuck Jenkins, nearing the end of his fifth four-year term, has been in office longer than any other sheriff in county history.
As an elected Republican in a place that gets rapidly more liberal each election, though, Jenkins, nearly 70, is also something of an endangered species.
Sitting in his super-sized Ford Expedition SUV outside a local American Legion post on a recent Tuesday, Jenkins tried to explain his long-running appeal.
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“I’m a regular guy that just happens to be sheriff.”
That means lunches like the one he’s about to have — a regular meeting with buddies where they’ll talk about the weather, make hunting plans and opine occasionally about the ways the country is going to hell.
He’s a Miller Lite man. He likes nights out at the Elks Club or dinner with his girlfriend, somewhere locally owned. Never a chain. A buddy cuts his hair — silver, in a neat crew cut — in a garage. He watches “The Andy Griffith Show” reruns every day. His beloved Frederick County is his very own Mayberry.
Even Jenkins’ views, previously on the fringe of the Republican Party, are now the norm.
He is an immigration hard-liner. Fox News once named him the second-toughest sheriff on immigration in the country, after Arizona’s Joe Arpaio. Last fall, at a candlelight vigil for the victims of the Oct. 7, 2023, terrorist attack in Israel, Jenkins likened undocumented immigrants to Hamas and suggested that there were terror cells hiding in America ready to do similar violence.
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Jenkins is cozy with top Immigration and Customs Enforcement (ICE) officials — he considers President Donald Trump’s border czar, Tom Homan, a friend. In 2008, Jenkins made Frederick County one of the first jurisdictions in the U.S to partner with ICE. Now, three other counties in Maryland participate in so-called 287(g) programs.
And that’s just immigration. He has also said the 2020 presidential election was stolen. And, like Trump, Jenkins believes he himself was the target of the kind of deep-state governmental conspiracy that the new FBI director and other Trump allies have railed about for years.
In 2023, Jenkins was indicted on federal charges that he helped a gun dealer illegally acquire machine guns. The case was dropped in November, right after Trump’s win, and after the other defendant was acquitted. Jenkins believes his prosecution was politically motivated, brought on after he posed for a picture with U.S. Rep. Lauren Boebert at the Mar-a-Lago Club — the president’s Florida enclave. Boebert was wearing a dress printed with “Let’s Go Brandon,” a euphemism bashing former President Joe Biden.
“That’s what put the target on my back,” Jenkins said.
His term ends next year. Jenkins eked out his last election victory, winning by fewer than 3,000 votes in a race where more than 105,000 were cast. Today, the county — a kind of exurban oasis about equally north of Washington and west of Baltimore, and growing in population thanks to migration from both — has more registered Democrats than Republicans. Five of the seven County Council members, the county executive and its congressional representative are now politically blue.
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Red-hot Jenkins said he’s running for a sixth term. Will he win? Who knows. But one thing is certain: While the world around Chuck Jenkins is changing, he says he won’t.
Glad-handing Chuck
Frederick County was a more bucolic place when Jenkins decided he should be its law-and-order man.
It was 2006, and the county was solidly Republican. Voters had not picked a Democrat for president since Lyndon B. Johnson in 1964.
Picture rolling farmland dotted with small towns on the edge of Appalachia — an increasingly bygone place where a low-level sheriff’s deputy who volunteered to fight fires, but hadn’t gone to college, could win election.
“He’s a good ole boy,” said Kai Hagen, a former Democratic county commissioner who also ran for office in 2006. “He’s good at retail politics.”
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Now, 19 years later, Jenkins is so renowned that random people stop him in public or approach him at restaurants. Even inmates do it.
On a recent tour of the county jail, Jenkins and acting warden Michael Cronise were explaining how they screen the immigration status of recent arrestees to determine if they need to alert federal officials. That’s when one man, wearing an old-timey striped jumpsuit, ambled over to interrupt with a simple greeting of, “Sheriff.”
Then he shook Jenkins’ hand.
Accessibility is part of Jenkins’ appeal. During their first campaigns, Hagen said, he would regularly run into Jenkins at town halls, community meetings, chicken barbecues or volunteer fire company benefit dinners.
Hagen said he and Jenkins weren’t friends, but they got along OK — until the sheriff checked out an Obama bumper sticker on Hagen’s car.
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“And it’s been downhill ever since,” Hagen said.
Like many Democrats in Frederick County, Hagen is a sharp critic of Jenkins, regularly faulting his close association with Trump, his immigration policies, the resulting lawsuits against the county, the sheriff’s inflammatory rhetoric and the federal prosecution that nearly cost Jenkins his freedom.
When the feds’ case went bust, Jenkins celebrated with a giant fundraiser at the Lewistown fire hall, and he estimates more than 800 people showed up. Chad Wolf, a former acting secretary of homeland security under Trump and current vice president of the America First Policy Institute, gave the keynote address.
“It was probably one of the largest, most largely attended events, maybe, in the political history of Frederick County,” Jenkins said.
Where Democrats see controversy, Jenkins’ supporters see not an extremist sheriff, but a hard-nosed cop who tells it like it is.
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“He’s 250 pounds and 245 of them are common sense,” one of Jenkins’ American Legion lunch companions said. Jenkins said he’s more like 230 pounds and the common sense came from his strict father.
Even though his last election was close, Jenkins won by a larger margin, and received more votes, than Democratic County Executive Jessica Fitzwater, who declined to comment for this story.
Law enforcement officials are typically judged by statistics. Is crime going up or down? How many murders were there last year?
Compared with places like Baltimore and Washington, there just isn’t that much crime in Frederick County. The sheriff’s office investigated 104 car thefts in 2023, the most recent year for which crime stats were available online. Baltimore Police investigate that many in a given week.
Frederick County is considered a safe place, and even the staunchest Democrats give Jenkins props for that.
“I give him a lot of credit for a lot of things,” said Carol Antoniewicz, a former social worker and local Democratic activist. “But his politics are ancient and prejudiced.”
The fight over 287(g)
In addition to appearances with some of the nation’s most conservative commentators, Jenkins makes time to interview with National Public Radio (NPR) and lobby the state’s liberal-leaning legislature. In a January NPR interview, Jenkins was asked whether enforcement would get more intense in Frederick County under Trump.
“I don’t believe it will,” he said.
Maybe that’s because it’s already been intense.
For 17 years, Jenkins has operated almost alone in Maryland in close cooperation with federal immigration officials now newly charged with stepping up the detention and deportation of people living in the U.S. without proper authorization.
The vehicle is the 287(g) program at the Frederick County Detention Center.
When a person is booked into the Frederick County Detention Center, a specially trained corrections officer asks a series of questions to determine whether they’re a citizen, and, if not, whether they’re here with appropriate documentation. If they aren’t, ICE can ask the jail to detain the person for 48 hours beyond when they would have otherwise been released.
A progressive group called Resources for Immigrant Support and Empowerment (RISE) has gone toe-to-toe with Jenkins over the 287(g) program in recent years, and worked to rally Democrats to their cause.
They say the local-federal cooperation unfairly targets Frederick County’s immigrant community, increasing the likelihood of deportation. Of the nearly 300,000 residents, about 1 in 10 are Hispanic and 1 in 5 speak a language other than English at home, according to U.S. Census data.
“Folks are very aware that something has felt different in Frederick as soon as you enter here,” said Sebastian Brown, a RISE member and strategist with the ACLU of Maryland.
On a recent morning in Frederick District Court, Judge Dino Flores Jr. worked through the criminal docket, a largely bilingual affair. Flores, a public defender and two private defense attorneys toggled between Spanish and English; a translator was also available.
Most defendants were there for misdemeanors, but one didn’t show up for a DUI sentencing. His attorney didn’t know where the client was.
The defense and prosecution approached Flores for an off-the-record conversation, but fragments could be heard. “Donald Trump being sworn in?” Flores asked.
The gist of their conversation was clear: The man didn’t show because he was scared he’d be deported after serving his sentence. The attorney didn’t return a request for comment.
In Trump’s America, administration officials regularly spotlight undocumented immigrants with violent crime backgrounds. In fact, overall, those cases tend to be rare, including in Frederick. The majority of deportation cases that originate from 287(g) programs in Maryland stem from misdemeanor or driving-related charges, like DUI, according to figures from the ACLU.
Jenkins, in several conversations, both plays up and plays down the risks posed by undocumented immigrants.
One moment, he might warn of the extreme dangers they pose to the community; how weak border security and ICE policies under Biden allowed murderous thugs, violent rapists and sinister gangs into Maryland to prey on innocent people.
In another, he will minimize the importance of his once-unique level of federal cooperation, saying 287(g) is “only a tool,” part of a general public safety mission. Of the 2,938 people who came through Jenkins’ jail in 2024, 71 had ICE detainers placed on them, according to the sheriff’s office.
“It’s such a very small part of what we do,” he said.
Even individuals with legal status to stay in the U.S. are concerned about being booked into Jenkins’ jail.
One man, who requested not to be named for fear of retribution, said he is fearful of being pulled over anytime he drives through Frederick. The man is otherwise living the American Dream: in his 30s, owns property in Frederick, has a family. But having been previously pulled over in Frederick County, and then deported, he said he doesn’t want to risk staying too long.
“I will return to Frederick when 287(g) is gone,” he said.
This year, lawmakers in Annapolis weighed a bill to outlaw 287(g) programs in the state, and activists testified extensively about the fear people have about increased enforcement. The bill did not pass. A separate bill blocking ICE from entering private areas of public schools and hospitals without a warrant did pass.
Jenkins, who testified in opposition to the legislation to bar local ICE agreements, has said he understands the fear, but concerns about discriminatory enforcement are misplaced because 287(g) is a jail-based program. However, there have been instances where the federal courts have found that Jenkins’ deputies engaged in discriminatory practices while out in the community.
On an evening in July 2018, Sara Medrano, a Latina woman who worked as a housekeeper, was driving to a friend’s house with her daughter and two infant grandchildren when a deputy pulled her over for a broken taillight — except Medrano’s taillights weren’t broken.
Speaking little English, she was detained for an hour while deputies tried to contact ICE. They wound up letting her go with only a citation because they couldn’t get in touch with federal agents, according to court records.
Medrano, with the help of the ACLU and RISE, sued Jenkins, the county and the deputies involved in federal court in 2019. The county settled the case in 2021 for $125,000. As part of the agreement, Jenkins apologized to Medrano in writing.
A separate case against Jenkins’ office was also settled in 2021. Sheriff’s deputies unlawfully arrested a woman from El Salvador while she was eating lunch on a work break and transferred her to ICE custody in 2008.
Jenkins didn’t apologize for that one.
Bingo night
After lunch with his American Legion buddies (he had a grilled cheese and soup), Jenkins embarked on a driving tour of the county, which was nostalgic and also not.
As he drove his Expedition through Woodsboro and Walkersville and Thurmont, he spoke glowingly of walking in parades or holding raffles to support a cause with guns for the winners. These little towns have changed little, and he likes that.
Those towns are on the north end of Frederick County. On the south end is Urbana, a newly developed area with gleaming townhomes, shopping centers and schools. Jenkins used to hunt on this land. Now you can walk, in a few steps, from the library to an Indian restaurant.
“None of us ever really want our homes and hometowns to change, I don’t think. And you know, towns can grow and things can change, but you don’t have to change the flavor of a community,” Jenkins said as he drove through it all. “Obviously, you get a big development like this or a community builds out, it’s going to change the flavor of the county, the look of the county.”
The flavor has changed most in the town of Frederick, where Jenkins was born and raised. The town is as liberal as liberal gets — Jenkins remarked that if you were to go into a coffee shop there, you’d be hard pressed to find a fan of his.
Some people don’t see that as a bad thing.
Frederick Mayor Michael O’Connor also grew up in the town and welcomes change. With more than 85,000 residents, Frederick is Maryland’s second-largest city, a place where people of all kinds want to live.
“Clearly, the political demographic shows more of those people are Democrats,” O’Connor said.
The town recently adopted all-resident voting for municipal elections, meaning anyone who lives in Frederick can vote in elections for the mayor and City Council regardless of where they live.
Jenkins is aware that this demographic change might suggest that his time as sheriff could be coming to an end. The Democrats are likely to run a stronger candidate against him in 2026 than they have for the last three elections. Should he lose, Jenkins expects 287(g) will go with him.
“I think anybody else that would ever be elected sheriff would get rid of it,” he said. “They don’t want the controversy that goes with it.”
The sheriff’s tenure over the last two years was nothing but controversy. The indictment was, start to finish, 587 days of “pure hell,” Jenkins said. Legal bills stacked up, his honor was tarnished. The feds even took his guns away during the case, an embarrassment for the gun-proud sheriff walking around in his uniform, forcibly disarmed.
“I had some pretty dark days, and I thought,‘Is it really all worth it?,‘” Jenkins said. “But at the end of the day, you gotta stand for something.”
Jenkins is now thinking about making a new stand. If he wasn’t indicted, he said, he would have run for Congress in 2024 in Maryland’s 6th District, which includes Frederick County, and the solidly Republican Washington, Allegany and Garrett Counties.
At the big party last fall celebrating his charges being dismissed, Jenkins asked the crowd what office he should run for next.
“Sheriff?” he asked to cheers. “County Executive?” More cheers. And then he asked about Congress
That got a cheer, too.
Neil Parrott, the Republican nominee, almost beat Rep. April McClain Delaney in the general election. Jenkins believes he could’ve beaten both.
In addition to his strong views on immigration, he’s got equally strong views on gun rights and government spending. It is easy to see Jenkins joining Andy Harris, Maryland’s lone Republican in Congress, in the Freedom Caucus.
And if Jenkins won, his life would be largely the same. He could do the same glad-handing and back-slapping at local community events that he loves, just with a different title.
The sun was getting ready to set when Jenkins ended his hourslong driving tour. But instead of heading home to Lewistown, the sheriff said he was off to the Elks Lodge.
It was his night to call bingo.
Correction: This article has been updated to correct that state legislation blocks ICE from private areas of public schools and hospitals without a warrant.
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