CHESAPEAKE – Elections will be held next November to fill a vacancy once Sheriff Jim O’Sullivan retires next month and will coincide with the general election.

Chesapeake Circuit Judge Marjorie T. Arrington ruled Monday that no special election is necessary and ordered that the sheriff’s election be held on Nov. 4, 2025, the date of next year’s general election, when other constitutional officials will be up for re-election. The failure comes later a formal request from the Chesapeake City Council, who voted last week to ask the court for an election date of November 4, 2025.

However, council members were divided and some pushed for a special election in April. Most voted in favor of an election in November, particularly to save the city the extra money it would cost to open the polls for a special election for sheriff.

O’Sullivan, who led the sheriff’s office since 2012, announced his retirement in September and will resign on November 1. His term will expire on December 31, 2025, and his deputy, Colonel David Rosado, will temporarily fill the position. Rosado is a 23-year veteran of the Chesapeake Sheriff’s Office and became Chesapeake’s first Hispanic deputy sheriff in 2022.

Natalie Anderson, 757-732-1133, [email protected]