Re-Elect Sheriff
Les R. Taylor

Moving the Winchester City Sheriff’s Office forward for all.

About Les R. Taylor


Sheriff Les R. Taylor traveled the world with his parents while his father served his country in the United States Army. Les Taylor moved to Winchester in 1996 and instantly fell in love with the area and its people. 

Les Taylor served proudly in the Army National Guard here in Winchester and in the Army Reserves for 10 years total with his last two years as Military Police. 

Les Taylor’s career in Law Enforcement started as a reserve deputy in 2001 with the Frederick County Sheriff’s Office. He became a fulltime deputy with Frederick County in 2002. Sheriff Taylor was assigned to the Northwest Regional Drug Task Force in 2006 and spent the next five years working with other jurisdictions in the war on drugs. He then went onto Criminal Investigations in 2011 until his election as the Winchester City Sheriff in November 2013.

Les Taylor has served in his community one way or another since he moved here in 1996. He volunteered as an Emergency Medical Technician for Greenwood Fire and Rescue, he taught CPR and First Aide classes at the local Red Cross. Les volunteered as a youth camp councilor for five summers. 

Les Taylor also attended Lord Fairfax Community College and received a Police Science certificate.


Since day one in office, Sheriff Taylor has improved safety in the Joint Judicial Center. Just a few examples of this; We have implemented a Special Response Team in place inside courthouse that quickens response time to in-house alarms and issues as well as added security for high profile cases and high profile prisoner movement. We have installed a total systems upgrade to JJC security to include cameras, access readers and panic alarms. We have implemented safer protocols for the handling and transportation of prisoners to and from court. We have implemented yearly active shooter training. Added electronic security procedures at the courthouse. 

We have been fiscally responsible; Negotiating corporate accounts at local parts stores for the acquisition of lower priced parts and negotiating corporate accounts at local oil changing station reducing the cost of that service and saving the time that the Deputy spends waiting. We have updated in-house in-service training thus saving time that the deputies would be spending on travel to and from the academy.

We have become a more professional agency even obtaining State accreditation by the Virginia Law Enforcement Professional Standards Commission. 

Community Involvement

Sheriff Taylor stated that being in law enforcement is not a 9 to 5 job, rather a 24 hour a day commitment. What he means by that is that you protect and serve, serve being a very important part. Being active in your community is not a job its just simply being a good community leader. 

Sheriff Taylor has partnered with local schools and libraries having deputies read to children. Sheriff Taylor has partnered with the SPCA to help get animals find forever homes. Created Shop with a Sheriff, taking children shopping for Christmas. Started a youth Explorer post, mentoring kids from ages 11 to 18 and teaching them about all aspects of law enforcement. Started a non-profit for better involvement between law enforcement and the community, Helped restart the Winchester/Frederick TRIAD Seniors and Law Enforcement Together program. Co-writing a childrens book "Deputy Knowles Knows" for charity. Installed a narcotics take back box inside the courthouse for community members to conveniently dispose of dangerous narcotics. Becoming more involved in community events, such as the yearly safety fair, National Night Out, Literacy Day and the Frederick Douglas Park Club Family Day.  


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Fundraiser For Friends of Les Taylor

July 24th 2017 630pm to 830pm 

El Centro Restaurant 

1 N Loudoun St, Winchester, VA 22601

25 dollars per person

Appetizers and Ice provided  

Frederick Douglass Park Family Day August 6th

9am- Youth Basketball Tournament  

12pm- Concession Stand & Vendors Open, Resource Fair 

1pm- Children's Games, Entertainment & Children's Free Lunch (lunch served 1-2:30) 

5pm- Conclusion of Resource Fair & Children’s Games

7pm- The Conclusion of Douglass Park Family Day 

No upcoming events.


Your support and contributions will enable us to keep Sheriff Les R. Taylor working for us, the citizens. 

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Senator Jill Vogel 

Sheriff Carlos Turner Surry Co Virginia

Sheriff  Robert P. Mosier Fauquier Co Virginia 

Delegate Chris Collins ​29th District

Jay Foreman Author and Frederick County School Board Shawnee 

Site Content

City Sheriff’s Office receives accreditation

By CHRISTOPHER EARLEY Winchester Star Jan 7, 2017  

City Sheriff’s Office receives accreditation

NORFOLK — The Winchester Sheriff’s Office was approved for accreditation, the Virginia Law Enforcement Professional Standards Commission announced Thursday.

It’s a designation that could pave the way for grants and discounts on the agency’s insurance policies.

Sheriff Les Taylor and Maj. Allen Sibert made the trip to Norfolk, where they appeared before the commission and answered questions about the office’s assessment, which included a three-day visit from commission officials.

“It was a long and tedious process,” Taylor said Friday. “And we had to prove we were doing everything to a professional standard.”

Sibert, who served as accreditation manager for the office, explained previously that the process began initially in 2014, when Taylor was voted into office.

What followed was an extensive, painstaking process that included making certain the office specifically followed the more than 600 procedures and standards set by the commission.

The office will now be required to re-apply every four years for re-accreditation

“It was one of the proudest moments of my career as Winchester Sheriff,” Taylor said of the accreditation, which he said combined the greatest efforts of all the deputies and administrative staff.

“We wanted to accomplish this and become accredited for the citizens of Winchester. They hired me to do a job and I wanted to do the best job for them, as they deserve a professional sheriff’s office.”

— Contact Christopher Earley at

City sheriff's office takes children Christmas shopping

Christopher Earley The Winchester Star Dec 11, 2016  

WINCHESTER — The city sheriff’s office on Sunday morning helped to make Christmas wishes come true for eight children living at the Henry & William Evans Home for Children during its second “Shop with a Sheriff.”

Funded by donations from citizens and businesses, Sheriff Les Taylor said four of his deputies teamed up with Target at 2340 Legge Blvd., where children ranging in age from 8 to 17 were taken on a shopping spree.

Taylor said donations were doubled from last year’s event, which helped to make the holidays that much brighter for children living at the Winchester home. One boy was able to buy a much-wanted electric guitar.

The nonprofit Evans Home provides a safe home for children who are in need. Each year, it serves an average of 25 children.

Taylor hopes to expand the event next year to include even more children.

“It warms my heart every time we can go out and do something for the community and youth any time, but especially this time of the year.”

— Contact Christopher Earley at

City Deputies help build trust with basketball hoop

Christopher Earley Mar 22, 2016 

WINCHESTER — All it took to spring Donald Finley Jr. into action was seeing a battered basketball hoop in the city’s North End neighborhood.

Located along a curb on East Street’s cul-de-sac, children flock to it daily, playing pickup games and putting up shots.

During a recent trip to the neighborhood to serve court papers, Finley, a Winchester sheriff’s deputy, saw the hoop as an opportunity.

First, the 33-year-old jumped into the mix with the kids — uniform, equipment and all — in part to bridge a gap he said often exists between children and law enforcement.

“They don’t see the badge anymore when we’re playing,” he said.

When the game was over, Finley decided to try and raise money for a new hoop.

It began with a Facebook post, Finley said, and grew from there.

At the Joint Judicial Center, a judge offered nearly $200 to buy the hoop, and several court employees chipped in to buy two basketballs, a pump and sand to fill the base of the portable hoop.

After Allen Sibert, a sheriff’s major, spent Tuesday afternoon assembling the hoop, he and Finley brought it to East Street.

It didn’t take long for a group of kids to put it to use.

“I’m feeling blessed,” said 13-year-old R.J. Britton, who lives nearby.

R.J. said that Finley’s visits have shown him and others that they can trust police officers.

But the new hoop is just the beginning for Finley, who said the community support was so generous that he plans to start a fund to be used as needed, whether it’s for new sports equipment, or simply water for kids playing outside during the summer.

As the son of a former Winchester city councilman and as a longtime resident, community service comes naturally to Finley.

“I’m just trying to build some trust with them,” Finley said, adding he hopes his interactions with kids will make them feel comfortable approaching officers when they’re in need.

“I still believe kids are the future,” Finley said. “But sometimes people don’t treat them that way.”

— Contact Christopher Earley at

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Goals for the next four years

Body Worn Camers

We have “body worn cameras” coming in the near future. This initiative will help with transparency and accountability.

Master Deputy Program

We have written new job descriptions for a “Master Deputy” program, another step in the deputies career development, advancing the quality of our deputies. 

Paper Service

We will be asking for new “paper service” software. We serve approximately 16,000 papers a year, the new software will streamline paper service for the deputies and admin saving time and saving money. 


We will continue to work hard to keep the sheriff’s office an accredited professional agency.

Continued Professional Service

We promise to continue moving the City Sheriff’s Office in a positive forward direction. 

To continue providing you with professional service. 

To continue excelling in safety and security of the courthouse and the citizens. 

To continue to provide strong community involvement. 

To continue to work with seniors and the area youth.