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Candidate Profile: R. G. “Ron” Montgomery (York Poquoson Sheriff)

R. G. “Ron” Montgomery is a candidate for the York Poquoson Sheriff. His name will appear on the ballot on November 7, 2023.

Montgomery is currently finishing the term of former Sheriff Danny Diggs. Montgomery is running against Scott Williams.


The first day of in-person early voting at your local registrar’s office for this election is Friday, Sept. 20, 2024. Click here to see who is on your ballot.

10 On Your Side reached out to all of the candidates running in this race with specific questions. The responses below came directly from the candidate and are unedited. If you do not see the candidate listed with a profile, we did not receive one.

Name: R.G. “Ron” Montgomery

Age: 69

Race: York-Poquoson Sheriff

Party: Republican

Website: https://www.facebook.com/MontgomeryForSheriff

Biography: Ron Montgomery is the Sheriff of York County and the City of Poquoson. He was appointed to this position by the Circuit Court Judge Richard Rizk on January 1, 2023, to fulfill the remainder of the term of retired Sheriff J.D. Diggs.

Sheriff Montgomery started his law enforcement career with the Sheriff’s Office in January of 1975. During his career he has been a patrol deputy, Major Crimes Investigator, Commander of the Major Crimes Division and has served as the Chief Deputy for the Sheriff’s Office since March of 2000. Sheriff Montgomery’s training and education includes a Bachelor of Arts Degree in Criminology from St. Leo University, the Police Executive Leadership School at the University of Richmond, leadership courses from the Southern Police Institute and numerous training courses through the Federal Bureau of Investigation and the Commonwealth of Virginia.

Sheriff’s Office Philosophy

Sheriff Montgomery is a strong proponent of community policing and has a history of establishing strong working relationships between the community and the Sheriff’s Office. Sheriff Montgomery established the Sheriff’s Office Citizen’s Advisory Committee in 2020 and this committee has been successful in establishing an even more effective means of collaboration and communication between the Sheriff’s Office and the community.

Other Areas of Service

Sheriff Montgomery is a member of the Virginia Sheriff’s Association, the National Sheriff’s Association, and the International Association of Chiefs of Police. He coached middle school football and baseball in York County and was the head baseball coach at Bruton High School for two years. He is a member of the York County Chamber of Commerce and is also on the Chamber’s Board of Directors. In addition, he is a member of the Grafton Kiwanis Club and serves on the Executive Board of the Boys and Girls Club as well as their Security Committee.

Personal Information

Sheriff Montgomery is a lifelong resident of York County and graduated from York High School. He and his wife Terri live in the Bruton area of York County and have five children and three grandchildren.

Why are you running for this office?

I have spent my entire career working for the York-Poquoson Sheriff’s Office. From the time I started with the Sheriff’s Office my goal was to someday become the Sheriff. I have worked for three Sheriff’s in my career, and I advanced in rank and responsibility under each. While working for my first Sheriff, A.S. “Sid” White, I served as a patrol deputy for four years and was promoted to the position of Major Crimes

Investigator. After four years of service as an Investigator, I was promoted to the rank of Captain of the Major Crimes Division. As Captain, I initiated the first case management system in the Sheriff’s Office. Under my second Sheriff, P.S. “Press” Williams, I was placed in charge of all law enforcement operations, which included the Uniform Patrol Division and the Investigations Division. I was also given the responsibility of Internal Affairs, overseeing the hiring process for the Sheriff’s Office, and preparing the annual Sheriff’s Office budget. Under the third Sheriff, J.D. “Danny” Diggs, I was promoted to the rank of Chief Deputy, where I supervised the daily operation of all five of the Sheriff’s Office Divisions, Administration, Uniform Patrol, Investigations, Community Services, and Courthouse Security/Civil Process. I continued to be the Internal Affairs officer and I coordinated the annual budget preparation and submission to the County. I was also responsible for presenting the budget to the County Finance Committee for consideration.

Some of my major accomplishments during my career are:

Establishing successful coalitions between the business community and the Sheriff’s Office to address specific crime trends

Establishing the Sheriff’s Office Citizens Advisory Committee

The selection, purchase, and installation of the Sheriff’s Office first computerized Report Management System

Addition of a Mobile Command Center to assist the office in dealing with major events

Adding In-Car Video systems to the Uniform Patrol Division

Adding Body Worn Cameras to the Uniform Patrol Division an Investigations Division

Developing a partnership with York County Fire and Life Services to start the County’s Drone Team.

Developing a partnership with the Autism Society of Tidewater to provide training to the deputies on how to interact with persons diagnosed with autism.

Developing a training program to educate the deputies on how to interact with person that have been diagnosed with Parkinson’s disease.

Developing a program with the York County School Division that allows deputies to read to and interact with elementary school students to foster positive relationships and enhance school security.

Adding technology to the Sheriff’s Office that greatly enhances the ability to investigate major crimes and provide critical evidence for the prosecution of these cases.

Meeting regularly with citizen and business groups to listen to concerns and develop programs to further assist the community and solve problems.

What is the most important issue facing law enforcement?

I feel the most critical issue facing law enforcement today is developing and maintaining a relationship with the community that we serve. Community policing is only successful if law enforcement and the community work together to identify problems, and work collaboratively to solve those problems. I believe that such a relationship exists between the York-Poquoson Sheriff’s Office and the citizens that we serve. When I interview law enforcement applicants that work for other agencies in the area, I am often told that the reason they want to work for this agency is the reputation we have for encouraging the deputies to take the time to interact with the community. Our deputies are encouraged to stop by the schools and meet both the principal and staff. In our elementary schools, the deputies take time to read to the students or eat lunch with them. Not only does this enhance school security, more importantly, it creates positive interactions between the Sheriff’s Office and these young children. that I believe these relationships will pay dividends as the children grow. I tell newly hired deputies to expect me to ask them occasionlly, what did you do to make York County a better place today for our citizens? It may not be that they made an arrest, or solved a crime, it may be as simple as changing a tire, or just listening to someone who needed a person to talk to. I call it the “Small Things Matter” program and I emphasize the importance of this philosophy to every member of the Sheriff’s Office. I understand how important our relationship with the community is, and I will build on the trust that the community has in this agency as your Sheriff.

How will you still value constituents and politicians with whom you disagree?

During my law enforcement career, I have often deliberately reached out to citizens and politicians that do not share the same opinion I have on assorted topics of public safety. After the George Floyd tragedy, I attended several community discussions in the county that were designed to bring the Sheriff’s Office and the concerned citizens together to talk about how this situation could have been prevented. There were many people at these functions that fully supported the York-Poquoson Sheriff’s Office, and that support is appreciated and not taken for granted. But I soon learned that engaging the people that did not share those same views was enlightening and led to some very productive conversations. I have told many people that I learned as much, or more, from those conversations than I did from many of the specialized classes I have attended. It was these discussions that led me to establish the Sheriff’s Office Citizen’s Advisory Board in York County. I approached two of the people that had been hosting these community talks and asked if they would be interested in serving as the co-chairpersons for this board. They accepted the roles and our Citizen’s Advisory Board was born. We received more than seventy-five applications to serve on the board. After the applications were reviewed, I had the two co-chairpersons select the board members. I asked specifically to make this group as diverse as possible because I wanted people on the board that were not necessarily proponents of law enforcement. I want to hear and understand their concerns. This board has been a success and it plays a significant role in the Sheriff’s Office’s community relations success.

I have found that when dealing with politicians, differing views are not necessarily an obstacle to working together. I have had success in my career discussing law enforcement issues with politicians and I have found that we find common ground when it comes to making the people, we serve feel safe and secure in their homes, work and school environments. I will continue to pursue these conversations as your Sheriff.