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Virginia Sheriffs' Institute
Supporting Virginia’s Sheriffs & Deputies

Fresh from graduating from the FBI National Academy, Chesapeake Undersheriff David Rosado took on a new challenge in June. On June 12-13, 2023, he completed a two-day Executive Management Leadership Training course with the Virginia Sheriffs’ Institute (VSI) in Lynchburg. The skill-based training focused on diversity, inclusion, and unconscious bias. Undersheriff Rosado now brings his new skills and certifications back to Chesapeake to help improve safety and communication throughout all of the local communities.


Shaping the children of today into the leaders of tomorrow: On June 13, 2023, Sheriff Jim O’Sullivan presented college students Jailyn Riddick and Emma Compton with a $1,000 scholarship certificate from the Virginia Sheriff’s Institute. The Virginia Sheriff’s Institute scholarship is open to college students majoring in criminal justice and political science at any Virginia university.



Sheriff Jim O’Sullivan and the Chesapeake Sheriff’s Office would like to congratulate Undersheriff Rosado on graduating from the 286th session of the FBI National Academy (FBINA) on June 8, 2023!

Undersheriff Rosado is a 22-year veteran of the CSO with a passion for community service, crime prevention, and protecting the elderly. Sheriff O’Sullivan appointed him to the position of Undersheriff in 2022.

Internationally known for its academic excellence, the National Academy offers 10 weeks of advanced communications, leadership, and fitness training. Participants must have proven records as leaders within their agencies to be admitted.

238 officers from around the world graduated from the prestigious law enforcement leadership academy. The 286th session of the National Academy consisted of men and women from 47 states and the District of Columbia. The class also included members of law-enforcement agencies from 25 countries, five military organizations, and six federal civilian organizations.

“I am so proud of David for completing this momentous achievement, “said Sheriff O’Sullivan. “I know firsthand the strength, fortitude, and determination needed to complete this program. I also know how invaluable the training was to make me the professional I am today. I look forward to Undersheriff Rosado bringing his new knowledge and expertise back to Chesapeake to help guide the Chesapeake Sheriff’s Office into the future.”


On June 9, 2023, CSO deputies volunteered at the swimming competition of Special Olympic Virginia’s Summer Games in Richmond. Deputies helped award medals to the recipients and congratulate all the participants. We had a blast supporting our SOVA athletes. Undersheriff David Rosado even issued the swimmers tickets for “swimming over the speed limit.”

Would you look at that, another state record shattered!


More than 80 CSO deputies pounded the pavement on June 8, 2023, for the Law Enforcement Torch Run for Special Olympics Virginia (SOVA)! Elite Unit Deputies Chad Allen and Kaitlin Dykes led the way with the Flame of Hope from the Chesapeake City Park to Chesapeake City Hall. With your help, the Chesapeake Sheriff’s Office raised a record $15,395 for the non-profit. This is the most money raised by a single agency in Torch Run history, a record we so proudly broke last year. We are so thankful to be a part of such a fantastic community and look forward to topping this record again next year.


The Hampton Roads Chamber held its annual Valor Awards at the Virginia Beach Convention Center on June 7, 2023. The chamber recognized first responders from all over Hampton Roads for their bravery, quick thinking, selflessness, and willingness to go above and beyond the call of duty.

This included our very own Investigator Scott Chambers who received the Ultimate Valor Award. Investigator Chambers was shot three times while attempting to arrest a homicide suspect with the US Marshals Task Force in January. After eliminating the threat, Inv. Chambers skillfully applied his own tourniquet. He is also a certified EMT. Sheriff Jim O’Sullivan proudly supported Inv. Chambers whom he called “not only his friend, but his hero”.

Congratulations to all the recipients! Sheriff Jim O’Sullivan along with the entire Chesapeake Sheriff’s Office thank you for your commitment to serving our community.