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.” Sheriffs are elected to four-year terms and do not have term limits.
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. 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.”
Since no Democrats are running in the general election, the Chesapeake Democratic Party’s leadership committee voted on July 10, 2025, to endorse Rosado. 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.”
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.”
Rosado started working at the Chesapeake Sheriff’s Office in 2001. During his tenure, he held multiple positions, including director of training, chief of administration, and director of corrections. In 2022, then-Sheriff Jim O’Sullivan (R) selected Rosado as undersheriff. After O’Sullivan left the office in 2024, Rosado became sheriff.
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.” 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.”
Chadwick started working at the Chesapeake Police Department in 2000. 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.” Chadwick also served in the U.S. Marine Corps from 1995 to 1999.
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.” 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.”
Chesapeake is also elections for commissioner of revenue, commonwealth’s attorney, and treasurer. Click here for more on those elections.