Chesapeake City Sheriff election, 2025
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| 2025 Chesapeake elections |
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| Election dates |
| Filing deadline: April 3, 2025 (primary); June 17, 2025 (general) |
| Primary election: June 17, 2025 General election: November 4, 2025 |
| Election stats |
| Offices up: Commissioner of revenue, commonwealth's attorney, sheriff, and treasurer |
| Total seats up: 4 |
| Other municipal elections |
| U.S. municipal elections, 2025 |
Incumbent Sheriff Dave Rosado (Write-In) and Wallace Chadwick III (R) are running in the general election for Sheriff of Chesapeake, Virginia, on Nov. 4, 2025. According to the sheriff's office official website, the office's "primary responsibilities include operating the Chesapeake Correctional Center, transporting inmates, providing security for all courts within the city, and serving as the law enforcement arm of the courts."[1] Sheriffs are elected to four-year terms and do not have term limits.[2]
Chadwick defeated Rosado 58% to 42% in the Republican primary on June 17, 2025. Following the primary, Rosado announced his campaign as a write-in candidate.[3] According to WTKR News 3's Maddie Miller, a write-in campaign is the only way Rosado can participate in the general election since Virginia law states that "if a candidate loses a primary race, their name cannot be printed on the general election ballot for that office."[3]
Since no Democrats are running in the general election, the Chesapeake Democratic Party's leadership committee voted on July 10, 2025, to endorse Rosado.[4] According to Bolts' Alex Burness, "Chesapeake is a purple city that has often voted for Democrats, including in four of the past five presidential elections."[4]
The Virginian Pilot's Natalie Anderson wrote, "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. [...] Rosado said the city is following all ICE best practices and has even expanded its partnership. [...] Chadwick, argues Rosado only began to hold inmates in custody on ICE detainers after Chadwick criticized the sheriff's office for not doing so."[5]
Rosado started working at the Chesapeake Sheriff's Office in 2001.[6] During his tenure, he held multiple positions, including director of training, chief of administration, and director of corrections.[6] In 2022, then-Sheriff Jim O'Sullivan (R) selected Rosado as undersheriff.[6] After O'Sullivan left the office in 2024, Rosado became sheriff.[6]
On the election, Rosado said, "I am running for the office of Sheriff because I have dedicated my career to serving and protecting the people of Chesapeake, and I am committed to continuing the steady, proven leadership our community deserves."[7] Rosado said his priorities would include "strengthening public safety, expanding programs that help reduce recidivism, protecting our seniors and youth, and making sure our staff have the resources and leadership they deserve."[7]
Chadwick started working at the Chesapeake Police Department in 2000.[8] In 2009, he founded Law Enforcement United, Inc., which, according to its website, works to "raise awareness of law enforcement officers who have died in the line of duty."[8][9] Chadwick also served in the U.S. Marine Corps from 1995 to 1999.[8]
On the election, Chadwick said, "For too long, the Chesapeake Sheriff's Office has operated under a system of nepotism and succession, leaving voters without a true choice in leadership. But this year is different. I am stepping forward to give Chesapeake voters a real option—one that puts integrity, accountability, and experience first."[10] Chadwick said his priorities would include "end[ing] catch-and-release permanently," "bring[ing] full transparency to the Sheriff's Office," and "keep[ing] our neighborhoods safe."[10]
Chesapeake is also elections for commissioner of revenue, commonwealth's attorney, and treasurer. Click here for more on those elections.
Candidates and elections results
General election
General election for Chesapeake City Sheriff
Incumbent Dave Rosado and Wallace Chadwick III are running in the general election for Chesapeake City Sheriff on November 4, 2025.
Candidate | ||
 | Dave Rosado (Independent) (Write-in) | |
 | Wallace Chadwick III (R) | |
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 = candidate completed the Ballotpedia Candidate Connection survey. | ||||
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Republican primary election
Republican primary for Chesapeake City Sheriff
Wallace Chadwick III defeated incumbent Dave Rosado in the Republican primary for Chesapeake City Sheriff on June 17, 2025.
Candidate | % | Votes | ||
| ✔ | | Wallace Chadwick III | 58.3 | 7,385 |
| Dave Rosado | 41.7 | 5,292 | |
| Total votes: 12,677 | |||
| = candidate completed the Ballotpedia Candidate Connection survey. | ||||
| If you are a candidate and would like to tell readers and voters more about why they should vote for you, complete the Ballotpedia Candidate Connection Survey. | ||||
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Voting information
- See also: Voting in Virginia
Candidate comparison
Candidate profiles
This section includes candidate profiles that may be created in one of two ways: either the candidate completed Ballotpedia's Candidate Connection survey, or Ballotpedia staff may compile a profile based on campaign websites, advertisements, and public statements after identifying the candidate as noteworthy. For more on how we select candidates to include, click here.
Party: Independent
Incumbent: Yes
Political Office:
- Chesapeake Sheriff (Assumed office: 2024)
Biography: Rosado started working at the Chesapeake Sheriff's Office in 2001. During his tenure, Rosado held multiple positions, including director of training, chief of administration, director of corrections, and undersheriff.
Show sources
Party: Republican Party
Incumbent: No
Political Office: None
Biography: Chadwick received a bachelor's degree from the University of Phoenix. His career experience includes serving as a police lieutenant in the Chesapeake Police Department and as the chief executive officer of Law Enforcement United, Inc. Chadwick also served in the U.S. Marine Corps from 1995 to 1999.
Show sources
Ballotpedia's Candidate Connection survey responses
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No candidate in this race has completed Ballotpedia's Candidate Connection survey. Ballotpedia is seeking 100 percent participation so voters can learn more about all the candidates on their ballots.
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Campaign advertisements
Election competitiveness
Polls
- See also: Ballotpedia's approach to covering polls
We provide results for polls that are included in polling aggregation from RealClearPolitics, when available. We will regularly check for polling aggregation for this race and add polls here once available. To notify us of polls available for this race, please email us.
Endorsements
Click the links below to see official endorsement lists published on candidate campaign websites for any candidates that make that information available. If you are aware of a website that should be included, please email us.
Election spending
Campaign finance
Candidates in this election submitted campaign finance reports to the Virginia Board of Elections. Click the links below to access those reports.
About the city
- See also: Chesapeake, Virginia
Chesapeake is a city located in the Commonwealth of Virginia. It is considered a county equivalent. As of 2020, its population was 249,422.
City government
- See also: Council-manager government
The city of Chesapeake uses a council-manager system. In this form of municipal government, an elected city council—which includes the mayor and serves as the city's primary legislative body—appoints a chief executive called a city manager to oversee day-to-day municipal operations and implement the council's policy and legislative initiatives.[11]
Demographics
The following table displays demographic data provided by the United States Census Bureau.
| Demographic Data for Chesapeake, Virginia | ||
|---|---|---|
| Chesapeake | Virginia | |
| Population | 249,422 | 8,631,393 |
| Land area (sq mi) | 338 | 39,481 |
| Race and ethnicity** | ||
| White | 59.7% | 66.3% |
| Black/African American | 29.7% | 19% |
| Asian | 3.4% | 6.7% |
| Native American | 0.2% | 0.3% |
| Pacific Islander | 0% | 0.1% |
| Other (single race) | 1.8% | 2.8% |
| Multiple | 5.2% | 4.8% |
| Hispanic/Latino | 6.5% | 9.5% |
| Education | ||
| High school graduation rate | 93.2% | 90.3% |
| College graduation rate | 34.6% | 39.5% |
| Income | ||
| Median household income | $81,261 | $76,398 |
| Persons below poverty level | 7.5% | 10% |
| Source: population provided by U.S. Census Bureau, "Decennial Census" (2020). Other figures provided by U.S. Census Bureau, "American Community Survey" (5-year estimates 2015-2020). | ||
| **Note: Percentages for race and ethnicity may add up to more than 100 percent because respondents may report more than one race and the Hispanic/Latino ethnicity may be selected in conjunction with any race. Read more about race and ethnicity in the census here. | ||
Election context
Chesapeake, Virginia Sheriff election history
2021
General election
General election for Chesapeake City Sheriff
Incumbent Jim O'Sullivan won election in the general election for Chesapeake City Sheriff on November 2, 2021.
Candidate | % | Votes | ||
| ✔ | Jim O'Sullivan (R) | 97.3 | 79,008 | |
| Other/Write-in votes | 2.7 | 2,167 | ||
| Total votes: 81,175 | |||
| = candidate completed the Ballotpedia Candidate Connection survey. | ||||
| If you are a candidate and would like to tell readers and voters more about why they should vote for you, complete the Ballotpedia Candidate Connection Survey. | ||||
Do you want a spreadsheet of this type of data? Contact our sales team. | ||||
Republican primary election
The Republican primary election was canceled. Incumbent Jim O'Sullivan advanced from the Republican primary for Chesapeake City Sheriff.
2025 battleground elections
- See also: Battlegrounds
This is a battleground election. Other 2025 battleground elections include:
- City elections in San Jose, California (2025)
- City elections in Washington, D.C. (2025)
- New Jersey gubernatorial and lieutenant gubernatorial election, 2025 (June 10 Democratic primary)
See also
| Chesapeake, Virginia | Virginia | Municipal government | Other local coverage |
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External links
Footnotes
- ↑ The Chesapeake Sheriff's Office, "Who We Are," accessed Sepetmber 14, 2025
- ↑ Code of Virginia, "Article 3. Sheriff. § 15.2-1609. Sheriff.," accessed September 15 2025
- ↑ 3.0 3.1 WTKR News 3, "Chesapeake Sheriff Rosado continues election campaign as write-in candidate after primary defeat," June 24, 2025
- ↑ 4.0 4.1 Bolts, "Democrats in Southeast Virginia Endorse “Pro-Trump, Pro-ICE” Sheriff," July 18, 2025
- ↑ The Virginian-Pilot, "Immigration enforcement at heart of divisive Chesapeake sheriff’s race," June 5, 2025
- ↑ 6.0 6.1 6.2 6.3 WTKR News 3, "Chesapeake swears in first new sheriff in 12 years," Noevmber 1, 2024
- ↑ 7.0 7.1 WAVY TV 10, "Candidate Profile: Dave Rosado (Chesapeake Sheriff race)," May 14, 2025 Cite error: Invalid
<ref>tag; name "WAVY TV 10 Rosado" defined multiple times with different content - ↑ 8.0 8.1 8.2 LinkedIn, "Wallace Chadwick," accessed September 14, 2025
- ↑ Law Enforcement United, Inc., "About Us," accessed September 14, 2025
- ↑ 10.0 10.1 WAVY TV 10, "Candidate Profile: Wallace W. Chadwick III (Chesapeake Sheriff race)," May 22, 2025
- ↑ City of Chesapeake, "Plan of Government," accessed August 26, 2014
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