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A Trump Favorite For His Hardline Anti-Immigration Stance, Maryland Sheriff Now Faces Re-Election

Frederick County Sheriff Chuck Jenkins seeks a fourth term as critics blast him for a record that includes poor jail conditions, in-custody suicides, and the deaths of two young people at the hands of his deputies.

Frederick County Sheriff Chuck Jenkins
Photo illustration by Anagraph/Photo by Mark Wilson/Getty

A Trump Favorite For His Hardline Anti-Immigration Stance, Maryland Sheriff Now Faces Re-Election

Frederick County Sheriff Chuck Jenkins seeks a fourth term as critics blast him for a record that includes poor jail conditions, in-custody suicides, and the deaths of two young people at the hands of his deputies.


The Appeal is spotlighting sheriffs across the country who are seeking re-election on Nov. 6. The rest of the series is available here.

On Oct. 7, 2008, Roxana Orellana Santos sat down on the curb to eat lunch outside her workplace in Frederick, Maryland, when she was approached by two Frederick County sheriff’s deputies. When they learned that Santos, who is from El Salvador, had an outstanding ICE warrant, she was arrested and transported to the Frederick County Adult Detention Center and then turned over to ICE; she remained in the agency’s custody for a little more than one month.

About one year later, Santos filed a federal civil rights lawsuit against the sheriff, the Frederick County Board of Commissioners, and several individuals with ICE and the Department of Homeland Security. She claimed that her Fourth Amendment rights—the right to be free from unreasonable seizure—were violated and that she was targeted because of her national origin, a violation of the Fourteenth Amendment. According to the lawsuit, the incident caused Santos “to suffer humiliation, emotional distress, physical pain and monetary damages” as well as fear that deputies would unlawfully arrest her or her family in the future.

The lawsuit also accused Frederick County Sheriff Chuck Jenkins of devoting “an increasingly greater share of [the county’s] resources to the enforcement of federal immigration laws,” specifically through its participation in the 287(g) program that allows deputies to carry out functions of federal immigration officers. Jenkins, the lawsuit alleged, created “a climate of fear among immigrants, Latinos, and those perceived to be of either or both groups.” In August 2013, the U.S. Court Court of Appeals for the Fourth Circuit ruled in Santos’s favor. Last month, a judge ruled that Jenkins and Frederick County are liable for damages in Santos’s arrest and detention.

Jenkins’s hardline anti-immigrant stance has helped him become a national figure in his 12 years as Frederick County sheriff. In 2014, after returning from a trip to the U.S.-Mexico border funded by the Federation for American Immigration Reform (labeled a hate group with white supremacist links by the Southern Poverty Law Center), Jenkins called for military deployment on the border. He’s now a go-to guest on Fox News to blast critics of ICE, and the conservative network included him in a 2011 list of “America’s Top 10 ‘Toughest’ Immigration Sheriffs,” second only to Joe Arpaio of Maricopa County, Arizona. In September, Jenkins was part of a group of sheriffs who President Trump feted at the White House. It was Jenkins’s second visit this year: In February, he joined Trump to discuss immigration policy and the Salvadoran gang MS-13.

But Jenkins faces re-election on Nov. 6. Under his leadership, Frederick County, home to about 200,000 people of whom 10 percent are Black and 9.5 percent are Latinx, was the first in Maryland to join 287(g). Jenkins’s record also includes poor jail conditions, multiple in-custody suicides as well the deaths of two young people at the hands of his deputies. In 2013, deputies sporting SWAT gear and night-vision goggles killed 19-year-old Daniel Vail while raiding the home he lived in with his mother. The same week, three off-duty deputies working a security detail wrestled Robert E. Saylor, a 26-year-old man with Down syndrome, to the ground after he wouldn’t leave a movie theater. Saylor died after he was handcuffed and forced from the theater.

Jenkins’s challenger is Karl Bickel, a veteran of both the Department of Justice’s Community Oriented Policing Services and the Frederick County Sheriff’s Office. Bickel has blasted Jenkins for what he says is the sheriff’s inattentiveness to the opioid crisis, but he has not come out definitively against 287(g); instead, he has simply called for an audit of the program.

Organizers with groups such as the ACLU of Maryland, Safe Haven Frederick, and the RISE Coalition of Western Maryland, meanwhile, have called for the shutdown of 287(g) in Frederick County. Safe Haven Frederick told The Appeal that immigrants traveling through the area know that they have to be careful, and that they are more likely to be asked of their immigration status or potentially arrested for something that they might not be arrested for elsewhere.  

A recent affidavit filed in Santos’s lawsuit shows that her experience of profiling by Jenkins’s deputies was not an anomaly. In July, Sara Medrano said that while driving home with her daughter, deputies stopped her and said she had a broken tail light. After the deputies inquired about Medrano’s citizenship, they attempted to call immigration officials to detain her but eventually let her go after officials did not answer the call.

Jenkins’s cooperation with ICE is not limited to 287(g); his office also has an agreement with ICE to house the agency’s detainees in Frederick County Detention Center, which has been criticized for its unconstitutional conditions. And in August, Maryland Public Defender Paul DeWolfe said the adult jail has been holding children under 18 in isolation for 23 hours per day while they await transfers to the juvenile detention center. Numerous studies have found that the trauma of solitary is particularly acute in young people because their brains are still developing.

Suicide has also been prevalent in the detention center. In 2013, two families sued Jenkins based on the treatment their loved ones received in Frederick County jails before they committed suicide. In October 2010, Valerie Miller, who had bipolar disorder and opioid use disorder, killed herself after being incarcerated for two days while experiencing withdrawal. The sheriff’s office refuses to provide drugs like Methadone and Suboxone that help those with opioid use disorders manage their addiction and alleviate withdrawal symptoms. Three months earlier, William John Hanlin died by suicide in the jail while being held in a solitary confinement unit. Hanlin also experienced severe withdrawal symptoms and his family’s lawsuit argued that the jail failed to provide him with proper treatment for his mental health issues or his substance use disorder.

When contacted by The Appeal, Sheriff Jenkins declined to comment on his office’s participation in the 287(g) program, Santos’ lawsuit, or the deaths in his jail.

Bickel, however, told The Appeal that people with substance use disorders should receive treatment, instead of jail time and a criminal record. For Bickel, Jenkins’s anti-immigrant stance is a distraction from serious issues plaguing Frederick County like fatal opioid overdoses.

“His focus on the immigration issue is for political reasons—trying to garner some votes from certain segments of the population by fearmongering,” Bickel said.

Rethinking prosecutors’ ‘second bite at the apple’ during parole proceedings

Rethinking prosecutors’ ‘second bite at the apple’ during parole proceedings


What you’ll read today

  • Spotlight: Rethinking prosecutors’ ‘second bite at the apple’ during parole proceedings

  • Solitary confinement, jail deaths rock race for sheriff in California

  • Louisiana judge threatens to appoint every eligible lawyer to death penalty case

  • Cooperation with ICE is on the ballot for the elections

  • Former guards allege abuse and mismanagement at a North Carolina jail

  • Edmund Zagorski’s attorney must have access to a phone before execution proceeds

  • Money is pouring in on both sides of marijuana ballot initiatives

In the Spotlight

Rethinking prosecutors’ ‘second bite at the apple’ during parole proceedings

This year, Debbie Sims Africa became the first member of the ‘MOVE Nine’ released on parole. Last week, her husband Michael Africa Sr. became the second. [Samantha Melamed / Philadelphia Inquirer] The couple, along with the five other surviving members of the group, was serving 30- to 100-year sentences for the death of a police officer who was fatally shot during a 1978 standoff in Powelton Village in Philadelphia. All nine maintained their innocence. (The 1978 incident was followed seven years later by the police department’s bombing of the MOVE compound that killed five children and six adults.) The couple was reunited with their son, born in Sims Africa’s jail cell, after 40 years.

In Sims Africa’s case, Martin Horn, a former corrections commissioner provided written testimony to the parole board about her “record of growing maturity, improved judgment and the assumption of personal responsibility,” and said he did “not believe that Debbie Sims is today a threat to the community.” [Ed Pilkington / The Guardian] In Michael Africa Sr.’s case, a retired guard told his attorney that “he had a spare room, and he would open up his home to Mike if needed, because of how much he trusted and respected him.” Africa had been denied nine times before his release. [Samantha Melamed / Philadelphia Inquirer]

The dispositive factor in the parole board’s change of heart may have been the support from District Attorney Larry Krasner’s office. In a letter supporting Sims Africa’s release, the first assistant district attorney wrote: “While Ms. Sims Africa’s crimes were very serious, her continued incarceration does not make our city safer. I am confident that she will not pose a threat to the Philadelphia community to which she wishes to return.” The parole board cited that letter in its decision. Two MOVE members who were also up for release at the same time were denied, and their denial letters cited the “opposition of the prosecuting attorney.” (The DA’s office said it had sent letters in support of their release as well. The parole board refused to provide clarification to media outlets, leaving it unclear whether it considered the DA’s recommendation or overlooked it and relied on old letters from the DA’s office opposing release.) [Sam Newhouse / Metro] Michael Africa Sr.’s lawyers said his parole was won thanks to a host of factors, including parole recommendations from the Philadelphia district attorney’s office. [Sam Newhouse / Metro]

Several Black Panthers and members of Black political movements remain in prison, serving decades-long sentences that began in the 1970s and 1980s. A few people have been released in the last year, despite virulent opposition from police unions and even elected officials. In Philadelphia, where Krasner has set out to make his office the “best progressive D.A.’s office in the country,” as Jennifer Gonnerman put it in her New Yorker profile, the office’s support for the couple’s release is consistent with that vision. But it is the rare exception among prosecutors who, even in an era when lengthy sentences are attracting new scrutiny, often oppose release on parole almost reflexively.

“What we see in New York State and across the country is prosecutors intervening in the parole release process in punitive ways,” Laura Whitehorn, a community organizer with the Release Aging People in Prison Campaign, told the Daily Appeal. “Having pursued the heaviest possible level of conviction and punishment during the trial and sentencing—the front-end of the legal process—prosecutors often get a second bite at the apple by recommending that incarcerated people be denied parole.

“This is even true in cases where there were plea deals,” Whitehorn continued. “The prosecutor negotiates a conviction and sentence that doesn’t carry the maximize prison time, but then years—often decades—later, they push to maximize prison time through parole denials. If the new wave of so-called progressive prosecutors really want to help end mass incarceration, they should seriously change the ways in which they intervene in the parole release process.

“Shockingly, this also happens in what’s called ‘compassionate release,’” said Whitehorn. “Across the country, elderly and ill people are denied release—even when they are within months of death—because the final decision rests with prosecutors and police, who continue to seek more punishment.”

In an article forthcoming in the Ohio State Journal of Criminal Law, professor Michael Cassidy calls for prosecutors to play little to no role in parole proceedings. He asks: “What is the ‘truth’ that a parole board is attempting to ascertain at a release hearing, and does the prosecutor play any legitimate role in that inquiry?” Cassidy believes that a prosecutor’s input at a parole hearing must typically be of “limited value,” given that much of what they can share will already be contained in the parole file. This question is of increased pertinence now for two reasons: First, the Supreme Court’s decisions in Graham v. Florida and Miller v. Alabama that have given people once sentenced to life without parole as young people the possibility of release. Second, the reckoning with the human and financial costs of mass incarceration that has led some states to reintroduce parole and others to consider it. [Michael Cassidy / Ohio State Journal of Criminal Law]

In Cassidy’s view, once outside the trial process, prosecutors must “eschew adversarialism and behave as ‘ministers of justice.’” Instead, he notes, there are numerous examples of prosecutors putting their “thumbs on the scale” of parole decisions, sometimes “offering a prediction of future behavior that as a professional matter [the prosecutor] is simply unqualified to make.” He advocates a two-part solution: action by state legislatures to limit the role of prosecutors in parole hearings and restraint on the part of prosecutors. Cassidy writes: “Each of the 38 states now providing some form of discretionary parole for adult prisoners allows prosecutors to give input in some fashion to the parole board. Unless prosecutors in those jurisdictions possess highly relevant, post-conviction information unavailable from documentary materials or the testimony of victims, I urge prosecutors to stay home and keep quiet.” [Michael Cassidy / Ohio State Journal of Criminal Law]

Stories From The Appeal

Santa Clara County Sheriff Laurie Smith and challenger John Hirokawa.
[Photo illustration by Anagraph/Photo via County of Santa Clara Office of the Sheriff/ Photo via John Hirokawa]

Solitary Confinement, Jail Deaths Rock Race for Sheriff in California. In Santa Clara County, incarcerated people, and a former undersheriff challenging six-term sheriff Laurie Smith, have turned conditions of confinement into a potent electoral issue. [Victoria Law]

Louisiana Judge Threatens to Appoint Every Eligible Lawyer to Death Penalty Case. After the state cut funds for capital defense, there’s a growing wait list of people in jail without a lawyer. [Emma Whitford]

Stories From Around the Country

Cooperation with ICE is on the ballot: In major counties nationwide, voters will decide next Tuesday the extent to which their local law enforcement agencies will cooperate with federal immigration authorities. ICE partners with local jurisdictions through different sorts of contracts, agreements, and grants. While the 287(g) program, which “allows local deputies to act as federal immigration agents,” is the most visible, some other types of agreement are more subtle and less transparently tied to immigration enforcement. In New Mexico’s Doña Ana County, for instance, the sheriff denies playing an immigration role despite the county’s participation in Operation Stonegarden, “a program through which the federal government provides localities with a grant in exchange for their assistance in border activities.” The Appeal: Political Report explores 10 counties—including Hennepin in Minnesota (Hennepin),  Wake in North Carolina (Raleigh), and Anne Arundel in Maryland (Annapolis)—where cooperation with ICE is on the ballot because of challengers who have pledged to reform it. [Daniel Nichanian / The Appeal: Political Report]

Former guards allege abuse and mismanagement at a North Carolina jail: Two former sheriff’s deputies at the Cherokee County Detention Center allege a culture of using some incarcerated people as “enforcers” to beat up others held at the jail. They also described a culture of mismanagement at the jail under the current sheriff, elected in 2014. There are two state investigations into violence at the jail underway, one involving a death in July of a man booked for marijuana possession and resisting officers. In June, Carolina Public Press published a report on allegations of excessive force by two guards. Since then, multiple community residents, former sheriff’s office employees, and people formerly held at the jail have contacted the publication regarding conditions at the jail. [Jordan Wilkie and Frank Taylor / Carolina Public Press]

Edmund Zagorski’s attorney must have access to a phone before execution proceeds: A federal judge has issued a temporary restraining order, ruling that Tennessee cannot proceed with Edmund Zagorski’s execution on Thursday unless his attorney is allowed access to a phone leading up to and during the execution. Prison officials can either comply with the order or appeal it to the Sixth Circuit Court of Appeals. The ruling came in response to a motion filed by Zagorski’s federal defender Friday in which she argued that it was necessary to have access to a phone during the execution to alert a judge in case anything went wrong. [Adam Tamburin / The Tennessean] See also If the state kills him on Thursday, Zagorski will be the first person executed by electric chair in Tennessee in 11 years.

Money is pouring in on both sides of marijuana ballot initiatives: An analysis by Marijuana Moment of the latest campaign finance data shows large contributions to political action committees that support or oppose marijuana ballot initiatives in Michigan and Missouri. In Michigan, the largest committee opposed to the legalization initiative has received over a million dollars from a national prohibition organization as well as $100,000 from Dow Chemical Corporation. Both the pro- and anti-legalization committees saw donations in the last nine days equal to a third of everything raised in the previous two months. [Polly Washburn / Marijuana Moment]

Thanks for reading. We’ll see you tomorrow.

Have a tip for The Appeal? Write to us at tips@theappeal.org. A good tip is a clear description of newsworthy information that is supported by documented evidence.

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Rural Oregon Sheriffs Lead Charge to Repeal State's Sanctuary Law

More than one dozen sheriffs support Measure 105 that would allow for cooperation with federal authorities even when an immigrant suspect has not been apprehended for any crime.

An immigrant identifying herself only as Vioney, who spent six months in an ICE detention facility, holds her grandson for the first time while being reunited with family members at Portland International Airport in Portland, Oregon, in September.
Photo Illustration by Anagraph / Photo by Mario Tama/Getty Images

Rural Oregon Sheriffs Lead Charge to Repeal State's Sanctuary Law

More than one dozen sheriffs support Measure 105 that would allow for cooperation with federal authorities even when an immigrant suspect has not been apprehended for any crime.


In 1977, Delmiro Treviño was sitting in a restaurant in Independence, Oregon, when police entered and began questioning him. Treviño was born in Texas, but officers harassed him about his ethnicity and his accent, and demanded proof of citizenship.

Treviño was humiliated in front of his friends, family, and the restaurant’s patrons.  He was also angry.

“Usually people backed down, because this kind of treatment was just a way of life,” said Rocky Barilla, an attorney who sued Independence on Treviño’s behalf. “They didn’t want to be in the crosshairs of local law enforcement. This guy complained.”

The case against the city was settled within a year, but Barilla saw racial profiling as a statewide problem. In 1986, Barilla became the first Latinx elected to Oregon’s legislature, where he drafted legislation to prevent state and local law enforcement from enforcing federal immigration laws as well as aiding in the apprehension of undocumented immigrants.

Oregon became the first state in the nation to pass a law limiting cooperation between local officials and immigration authorities, often described as a “sanctuary law,” a measure that has been adopted by an increasing number of politically left-leaning municipalities in the absence of federal immigration reform.

Oregon’s law passed in 1987 with bipartisan support. It was enacted soon after the Immigration Reform and Control Act of 1986, signed into law by President Ronald Reagan, offered a path to citizenship for millions of undocumented immigrants.

But Oregon’s law is now facing a repeal effort, in part because of tensions around immigration inflamed by President Trump, who has promised a crackdown on “sanctuary cities,” new restrictions on legal immigration, and a wall at the U.S.-Mexico border.

The group leading the effort, Oregonians for Immigration Reform (OFIR), was listed as a hate group by the Southern Poverty Law Center because of its ties to border vigilantes including one who has referred to immigrants as “Mexican Nazis.” OFIR has found success at the polls in the past, helping pass a statewide initiative in 2014 that prevented undocumented immigrants from obtaining driver’s licenses. And the repeal effort has financial support from anti-immigrant group Federation for American Immigration Reform, a leader behind the scenes in shaping Trump’s immigration policies.

Oregon law enforcement is divided on the state’s sanctuary law. But 16 sheriffs from rural counties, led by Clatsop County Sheriff Tom Bergin, who is also the former president of the Oregon State Sheriffs’ Association, signed a letter calling for its repeal. In the Trump era, sheriffs like Bergin are among the most prominent voices on immigration policy; in early September, a group of sheriffs met with the president at the White House to “re-establish the rule of law” on illegal immigration. In an interview with The Appeal, Bergin said that two more sheriffs later added their support to his letter, totaling half of the state’s 36 sheriffs.

In the letter, Bergin dismissed the idea that the sanctuary law’s repeal would “unleash a wave of profiling of Hispanics” because law enforcement undergoes anti-profiling training; he also assured Oregonians that “I have never witnessed an instance of racial profiling from any of my deputies.”  And Bergin wrote about the July murder of Iowa student Mollie Tibbetts, allegedly at the hands of Cristhian Bahena Rivera whom Trump described as a “horrible person who came in from Mexico.” Despite the fact that Rivera’s immigration status is unknown, Bergin insisted in the letter that Oregon’s sanctuary law “compounds” the “neglect” that led to Tibbetts’s murder.

“This has nothing to do with being prejudiced,” Bergin said. “It boils down to the rule of law.”

The repeal effort, known as Measure 105, would allow for cooperation with federal authorities even when an immigrant suspect has not been apprehended for any crime. Under current law, ICE can still seek criminal warrants to keep suspects detained locally. Some law enforcement agencies in Oregon regularly turn over jail booking reports and mugshots to federal immigration agencies.

In May, the American Civil Liberties Union and the National Immigrant Women’s Advocacy Project released a survey in which law enforcement reported increasing difficulty in obtaining cooperation from crime victims who are undocumented immigrants. According to the report, which connects such mistrust to the immigration policies of the Trump administration, 67 percent of participating officers said they believe immigrants’ fear has hindered their ability to help victims of crimes.

In August, Washington County Sheriff Pat Garrett and District Attorney Kevin Barton released a statement opposing Measure 105, saying a repeal of Oregon’s sanctuary law would lead to “a patchwork of inconsistent ordinances and rules from various cities and counties.”

“Immigrant communities and families may become greater targets for criminals because they may be less likely to come forward or appear in court to testify,” they wrote. “These are not hypothetical concerns; we have already seen these issues occur.”

Measure 105 appears likely to fail on Nov. 6, but polling suggests that there are a significant number of undecided voters. A poll conducted by Oregon Public Broadcasting from Oct. 4 to 11 shows 45 percent of voters opposed to Measure 105 and 32 percent in support, with almost one quarter undecided.

Immigrant rights advocates caution that in a midterm-year voter turnout may be unpredictable. “A growing majority of Oregonians oppose Measure 105, but we are not taking any vote for granted,” Peter Zuckerman, a “No on 105” campaign spokesperson, told The Appeal. “We are canvassing, phone banking, holding house parties. The bottom line lesson for us is we can’t take any vote for granted.”

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