Democrats in Southeast Virginia Endorse “Pro-Trump, Pro-ICE” Sheriff

The Democratic Party in Chesapeake, Virginia’s second-largest city, has embraced and endorsed the local sheriff who proclaimed his office “pro-Trump, pro-ICE,” and who campaigned as a Republican this year as “Detain ‘Em Dave Rosado.”

This comes after Rosado lost the June 17 GOP primary to Wallace Chadwick, a local police lieutenant who pitched himself as an even more loyal ICE ally than Rosado.

Following his loss, Rosado vowed to stay in the race and promptly launched a write-in campaign for the November general election, asking local Democrats for their support. 

Chesapeake is a purple city that has often voted for Democrats, including in four of the past five presidential elections. But no Democrat or independent had filed to run for sheriff in advance of a mid-June deadline, to the immense frustration of local immigrant rights advocates who’d hoped to have an alternative to rally around. “It blows my mind that there’s no opposition,” Maida Dooley, an organizer in the region, told Bolts in early June, calling local party leadership complacent. “Maybe they don’t care,” she said. 

In the ensuing weeks, rather than recruit a challenger of their own to Rosado or identify an alternative write-in candidate who’d take advantage of GOP divisions, the local Democratic Party decided to support “Detain ‘Em Dave Rosado.”   

On July 10, the Chesapeake Democratic Party’s leadership committee voted overwhelmingly to endorse Rosado. The party, which now plans to advertise his write-in campaign and include his name on sample ballots it’ll send out to voters, also approved Rosado joining the leadership committee.

“He was the candidate that was in line with our values,” local party chair David Washington told Bolts. 

The Democratic endorsement stings for local immigrant rights organizers not just because of Rosado’s rhetoric during the GOP primary but also due to his actions in office to collaborate more closely with ICE.

Rosado announced in June he’d signed a new contract with ICE to allow it to house some of its detainees inside the Chesapeake jail—a key convenience for ICE, which has no detention facility of its own in that area. 

And not long before that, in March, Rosado updated his office’s internal policy to begin honoring so-called ICE detainers, which are requests from federal immigration agents to keep incarcerating people days beyond their scheduled release date, giving ICE more time to arrest them. Chadwick has not named any policies he’d pursue beyond those Rosado has already implemented this year.

Washington, the local Democratic party chair, told Bolts that Chadwick was an “unacceptable” pick for sheriff and specifically cited his loyalty to ICE as a leading reason why his party must now support Rosado. In an interview, Washington also said he opposes local law enforcement cooperation with ICE: “Police are being deputized into snatching people up because of the color of their skin, and we don’t support that.”

But when asked how he squares these positions with Rosado’s actions in office, including the fact that the sheriff signed a new detention contract with ICE just last month, Washington said he was unaware of those details. “This is my first time hearing about any signed contract,” he said. “That’s something I’m going to have to follow up with him about and get clarification on.”

The next day, Washington emailed Bolts an updated statement of unequivocal support for Rosado, calling him “the right choice to continue leading with professionalism, accountability, and a steadfast commitment to justice.”

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Blaizen Buckshot Bloom, a vice chair of the local Democratic Party, regrets that Democrats did not compete in this race to start, though they echoed a point that Washington also made about the party’s recruitment challenges: Would-be Democratic candidates, Bloom told Bolts, were scared to challenge a law enforcement power structure that, in Chesapeake and nationwide, leans hard to the right.

But Bloom said that embracing Rosado should be a step too far for local Democrats.

“Voters can go for who they think is the best candidate, and if there are two conservatives and you’re going to vote for one because you think they’re the lesser evil, that’s fine,” Bloom said. “But his [Rosado’s] views, his values are incompatible with the party, and I don’t think the Democratic Party should be playing favorites in the conservative-versus-conservative election.”

Jeff Staples, who joined the Chesapeake Democratic Party’s leadership committee in 2005 but then left in 2011 out of frustration at party heads, says he was not surprised by its decision to endorse Rosado given his own observations over many years. “They’re doing nothing to build any ground game in Chesapeake,” he said, adding that the party has a history of embracing staunch conservatives.

Virginia has no requirement for local write-in candidates to file paperwork by a particular deadline. So even with no Democrat filing by the June primary, Chesapeake Democrats could have still tried to find a candidate more supportive of immigrant rights to run as a write-in against Chadwick and Rosado. The party committee did not discuss that option at its July 10 meeting, attendees told Bolts.  

To the contrary, party leaders were eager to anoint Rosado, and multiple local elected officials, including state Delegate Cliff Hayes, spoke publicly on his behalf, according to several people on the committee who spoke with Bolts. (Hayes’ office did not return a request for comment.)

When it came time for the committee to vote on whether to endorse Rosado, members were asked to hold up a voting card—green for support, red for opposed.

“I saw a sea of green, and myself as the only red,” said D.J. McGuire, a committee member and an advocate for immigrants’ rights. Just two days prior, McGuire had spoken to Chesapeake’s city council to urge it to cut off any local cooperation with ICE.

Rosado, McGuire added, hardly renounced his approach to ICE cooperation. “He gave vague statements about upholding the law, keeping the citizens safe, blah blah blah,” McGuire said. He was frustrated that Democratic leaders in the room who supported Rosado seemed to look past his record: “I got the feeling that for a lot of folks there, especially some of the local elected officials, they felt this [scrutiny] was all a distraction.”

In a June Facebook post in which he boasted about his ICE partnership and Trump loyalty, Rosado wrote, “Want to know where I stand? Call me directly at [his phone number] — I’m happy to talk.”

Bolts has called and texted Rosado many times since May, both before and after the primary. He has never responded.

McGuire, who used to be a Republican but quit the party after Trump emerged as its leader last decade, says he was one of only a few people to press Rosado at the July 10 meeting.

In answer to one of his questions, McGuire said, Rosado did promise that he would not support ICE raids at local schools or courthouses and that he would not sign a 287(g) agreement with ICE. The 287(g) program formally deputizes sheriff’s officials to act on ICE’s behalf; hundreds of sheriffs around the country, including 19 in Virginia alone, have rushed to join the program since Trump returned to office.

Chadwick and Rosado never debated during the GOP primary and have no debate planned as of now. It’s unclear what daylight currently exists between them in terms of immigration enforcement policy, which has been the focus of Chadwick’s campaign; in an interview with Bolts, Chadwick did not propose any specific actions in that area to build upon Rosado’s recent record or say whether he would sign a 287(g) agreement, telling Bolts only that he would evaluate department policies if and when takes office.

Chadwick said of Rosado, “I find it very hard to believe now that he’s adopting Democratic values and that’s the party he wants to go with. That says a lot about someone who will change their fundamental values to keep their job.”

Washington, the local party chair, said the Democrats did not seek any policy concessions from Rosado in exchange for the endorsement. 

He also said that Rosado explained to him that the “pro-Trump, pro-ICE” rhetoric of his primary campaign was designed at the advice of GOP consultants. 

“According to him, the people in charge of his campaign said some things he didn’t necessarily agree with, in terms of what the messaging was,” Washington told Bolts. “That’s his position. All we can do is respect that.”

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Virginia Beach, the largest city in the state, has its own sheriff race this year, with some striking similarities to the situation in neighboring Chesapeake: Virginia Beach Democrats also failed to nominate anyone to run against their Republican sheriff, Rocky Holcomb, despite the city also being winnable ground for Democrats. (Trump lost in Virginia Beach in 2020 and 2024).

One local Democrat mounted a last-ditch effort to challenge Holcomb last month: Having read a Bolts story published in early June on the lack of competition in sheriff races across Virginia, Fergie Reid, a longtime political organizer who has worked on recruiting Democratic candidates in Virginia, attempted to find a Democrat to run for sheriff in Virginia Beach, and, within days, he connected with Amber Phelps, who leads a local organization opposing prison labor. 

Phelps decided she wanted to jump into the race, telling Bolts ahead of the primary that she hoped to at least present voters a vision of decarceration. 

But the regular deadline for candidates to file for local office had long since passed, so Phelps needed the approval of local party leadership by June 17. Virginia Beach Democratic Party leaders declined to call a last-minute caucus meeting to consider nominating Phelps, saying they lacked the ability to do so within seven days of that date; Phelps says she approached party leaders 10 days before the deadline. 

As a result, Holcomb will run in November with no Democratic opponent, though he’ll face independent Aldo Dibelardino, who talks of jails as “soul hospitals” and whom Holcomb already defeated easily in a previous election. 

Phelps told Bolts this week that Democrats missed an opportunity by failing to place a sheriff candidate in Virginia Beach, but that Democrats’ endorsement of Rosado in neighboring Chesapeake is a particular insult to anyone opposed to Trump’s deportation agenda. 

“This guy has clearly stated what his values are, and we’re going to completely ignore that and put the Democratic endorsement on him?” Phelps said. “It honestly hurts my heart as a Democrat. When your own party is failing you, where do you go?”

This fall, voters in southeast Virginia and across the state will have plenty of other chances to weigh in on races affecting immigrant rights. Most notably, Virginians will decide who will replace Republican Governor Glenn Youngkin and also decide every seat in the state House. 

Immigration has been a hot topic in the governor’s race: Democratic nominee Abigail Spanberger has criticized Trump’s approach to deportations and argued that local law enforcement should not be enlisted to support ICE. Her opponent, Republican Winsome Earle-Sears, says Virginia law enforcement should become more active in assisting ICE, telling Fox News that she would “deputize state police” for that purpose.

If Spanberger wins and Democrats hold the state House, the party would gain control of the state government, and they’d thus have power to regulate local governments’ collaboration with ICE.

But potential Democratic gains in Richmond are cold comfort to those in southeast Virginia who are frustrated by the lack of competition in Virginia Beach and by Democrats embracing Rosado in Chesapeake.

Said Phelps, “We need people we can believe in right now, candidates we can support without wondering if they’re going to flip.”