Immigration enforcement at heart of divisive Chesapeake sheriff's race

CHESAPEAKE — One of the region's most divisive races in this election cycle is between two Republicans vying to be Chesapeake's fourth elected sheriff.
At the heart of the division in the race is the city's immigration enforcement and cooperation with U.S. Immigration and Customs Enforcement, or ICE. Sheriff Dave Rosado said the city is following all ICE best practices and has even expanded its partnership. But his opponent, Chesapeake police officer Wallace Chadwick III, argues Rosado only began to hold inmates in custody on ICE detainers after Chadwick criticized the sheriff's office for not doing so.
Chesapeake Republican party members on the local, state and federal level are not a united front, and have split support among the two men.
The Republican primary is June 17. No other candidates have filed to run as Democrats or Independents, so whoever wins the primary would be the presumptive winner in the fall and secure a 4-year term. The sheriff's office handles jail security, courthouse security, civil enforcement and the school resource program, among other duties.
Rosado took the reins in November to fulfill the remaining term for former Sheriff Jim O'Sullivan, who retired after more than a decade. Rosado worked in the Chesapeake Sheriff's office for more than 20 years and became the city's first Hispanic undersheriff in 2022. In the office, he's overseen jail operations, expanded the school resource officer program for elementary schools and led anti-bullying initiatives for students.
'I've been with the office for 20 years, worked all sections of the jail, and I truly love what I do. And I want to continue serving the city,' Rosado said. 'There's no trying to get to know the job. I'm ready today because I've been doing the job.'
Chadwick is a U.S. Marine Corps veteran and currently serves as a lieutenant and executive officer of the police's Special Operations Division and oversees the maritime operations unit. He's thrown his hat in the race to push against what he said is a tradition in Chesapeake of grooming someone internally within a 'good ole boys' network to step up and take over. He said he was compelled to run to change the 'culture' of the sheriff's office and give deputies 'a voice.'
'We've only had three elected sheriffs since 1963 and those elected sheriffs have been generationally passed down to the next guy,' Chadwick said. 'So essentially, they're grooming someone to take over their position and doing everything they can to assure that that way of life goes on.'
If elected, Chadwick said he also wants to boost recidivism and rehab programs in the jail as well as change and update data systems for more communication between the sheriff's office and the police department.
At the heart of Chadwick's campaign, however, is his criticism of how he said the sheriff's office has failed to cooperate with ICE under Rosado's leadership.
ICE detainers are requests to local law enforcement to hold a person in custody for 48 hours past their scheduled release to give federal authorities time to pick them up them for possible deportation proceedings. In the past, federal courts have found some local law enforcement agencies liable for unconstitutional detentions under ICE detainers. Last year, New York City agreed to pay $92 million in damages to immigrants who were unlawfully detained beyond scheduled release dates.
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Chadwick alleges the Chesapeake Sheriff's Office was not honoring ICE detainer requests under O'Sullivan or Rosado — at least until he pointed it out and made it a talking point of his campaign. Chadwick's campaign website includes a host of documents he said he received through Freedom of Information Act requests, including emails and memos regarding the city's immigration enforcement policies. Chadwick slams Rosado for releasing a 'convicted child sex predator' instead of holding him for 48 hours before releasing him into ICE's custody.
'The right thing for him to do would have been to take full accountability and say, 'You know what? This was pointed out. We are now changing our policy. We are now in full compliance,'' Chadwick said. 'I would not have had an argument after that, because he came out, took accountability and said, 'Yes, we're doing it.' Instead, he doubled down. He said, 'We've always complied with ICE.''
Rosado denies those assertions. He said he adopted all existing policy when he assumed the role in November, and then policy was reviewed and updated in March following an executive order from Gov. Glenn Youngkin in February requesting sheriffs certify compliance with ICE.
The primary update was the implementation of a 48-hour detainer hold, which wasn't part of the policy in November. But after talking with other sheriffs about the executive order, Rosado said Chesapeake implemented the 48-hour hold, deemed an ICE best practice.
He explained that when someone is jailed for a charge, ICE is contacted if it's an undocumented immigrant, then contacted again five days before release and each subsequent day until release.
And as of this week, the city's ICE partnership was expanded to allow 72-hour holds, which Rosado said gives ICE extra time to process detainers without needing to travel hours away. Rosado said it was possible due to decreased restrictions under the federal administration.
'If (ICE) cannot come or make arrangements for transport at that time or prior, then legally, I cannot keep someone in our facility if the judge has released them, or their time is up, or if they make bonds,' he said.
Rosado said when he took over in November, 24 people in the Chesapeake jail had ICE detainers. He said ICE has since picked up most of them, two were transferred to another facility, and four remain in custody.
'It doesn't happen a lot. We are very fortunate that Chesapeake doesn't have those issues,' Rosado said. 'We don't have illegal immigrants running (rampant) in the city … and we do not have dangerous criminal illegal aliens being released by me or this jail into our community. So that is not true, and we work closely and have a great partnership with ICE.' ']
Rosado said he believes the attacks from his opponent are politically motivated.
'That's a narrative that someone who doesn't have their strategy is just to be negative when they have nothing to stand on or nothing to represent,' Rosado said. 'My opponent, he's a good cop, and I'm sure that in his role as traffic lieutenant, he's doing a good job, but I couldn't do that job. I don't know what makes him think that he can do my job.'
Local, state and federal Republicans are split on who they're backing in the race. Rosado touts endorsements from U.S. Rep. Jen Kiggans, Virginia Sen. Christie New Craig, Virginia Del. Barry Knight, Mayor Rick West, former Chesapeake Sheriffs John Newhart and O'Sullivan, the Chesapeake Fraternal Order of Police and council member Jeff Bunn. Rosado also boasts the endorsement of Tony Pham, assistant secretary for border and immigration policy in the U.S. Department of Homeland Security.
Meanwhile, Chadwick has in his corner former Congressman Randy Forbes and wife Shirley, outgoing Virginia Del. Baxter Ennis, Virginia Sen. Bill DeSteph, Vice Mayor John de Triquet, former Commonwealth's Attorney Nancy Parr, council members Amanda Newins and Daniel Whitaker and the Chesapeake firefighters' union.
As for money in the race, Rosado boasts a more powerful war chest of $218,131 in campaign donations as of March 31. Among his biggest donations are $2,000 from New Craig's campaign committee, $1,000 from Historic Greenbrier Farms owner Kent Basnight and $5,000 from Collins Machine Works.
Chadwick has received $75,664 in donations as of March 31, including a $4,743 loan from himself. Donations include $1,000 from Newins' campaign and $1,000 from her individually, $1,000 from Whitaker, $300 from Triquet and a $7,500 in-kind donation from DeSteph.
Natalie Anderson, 757-732-1133, natalie.anderson@virginiamedia.com

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