Clarke County Sheriff Tony Roper (right) has endorsed Frederick County Sheriff Lenny Millholland’s re-election bid.

WINCHESTER — Clarke County Sheriff Tony Roper has endorsed Frederick County Sheriff Lenny Millholland in the Nov. 5 election.

Millholland is seeking a second four-year term as an independent. He is being challenged by Republican nominee Allen Sibert, who has been endorsed by Winchester Sheriff Les Taylor and former Frederick County Sheriff Robert Williamson.

“I have known Lenny Millholland since I became involved in law enforcement some 40 years ago,” Roper said in his written endorsement. “In his early days with the Winchester Police Department, [Millholland] was known for his relentless pursuit of criminals. He seemed to understand just how important his chosen profession was, always understanding that he worked for people who came to him when they needed an advocate. His genuine feelings for others was clear, and I watched him navigate successfully a criminal justice system with compassion for victims, integrity when dealing with other members of the prosecution teams, and even suspects.”

Roper, who has been Clarke County’s sheriff for 16 years, described Millholland as “well-respected by his peers” and said he understands the office.

“I have found in life that the strongest indicators of what a person will do in the future in any given circumstance is how they have performed in the past,” Roper’s endorsement said. “We do not have to guess how Lenny Millholland will proceed in this role — we need only look at his body of work. The people of Frederick County have the luxury of a large body of the sheriff’s successful work to examine.”

In response to Roper’s endorsement, Millholland said: “I am honored that Sheriff Roper felt that as a sheriff I have made a difference for the citizens of Frederick County and those of the Commonwealth.”

— Contact Josh Janney at

(5) comments

Joe Crane

Sheriff Roper, please keep your opinions within the boundaries of Clarke County.


I guess John Baker wasnt available?!


Another Democrat Endorsing Millholland

Sheriff Millholland says he is an Independent and that Sheriff’s should not be involved in politics But Actions speak louder than words.

In 2013 AND 2017 Sheriff Millholland used the weight of his office to Endorse Democrat Mark Herring for Attorney General in 2017 he endorsed Ralph Northam for Governor.

I personally believe if an elected official uses the weight of his office to endorse candidates and influence voters then the candidates need to have views most aligned to his constituents. Mr. Millholland must agree with their policies or he wouldn’t have endorsed them.

I hope every voter realizes that a vote for Millholland is a vote for Democratic ways especially in reference to our Gun rights and Sanctuary Counties (There are 3 counties in Va already that are sanctuary Counties – Fairfax, Arlington & Chesterfield) and two of those Sheriffs joined Millholland in endorsing Northam for Gov. in 2017.

I can see Frederick County being added to that list especially since Millholland said he’s confident most sheriffs would need to hear a good reason before aiding in ICE operations. Local law enforcement isn’t going to help round up people who haven’t broken any local laws. “It’s not going to happen in Frederick County,” he said. “Not so long as I’m sheriff.” (Does someone need to become a victim before he might act)

When you endorse someone and help them get into office you are partially responsible for their decisions. Mr. Millholland should remember Virginia Democratic Gov. Ralph Northam is facing backlash after he voiced his support for a state measure that would significantly loosen restrictions on late-term abortions.

Learn more about Siberts Platform on Facebook “Sibert for Frederick County Sheriff” and I am sure you will agree with me.

Take time to VOTE Nov. 5th - Sibert for Frederick County Sheriff


You should always vote for the BEST person to do the job. Not just vote a ticket. The Democrats of today are not what they were when I was growing up. Sam Irving and Strom Thurman are turning over in their graves at what the Democrats have become.


I agree, Vote for the BEST man and this time it is NOT Mr. Millholland.

Along with many local officers I am livid that Mr. Millholland is so desperate that he would bring Ricky Timbrooks murder into the campaign. He apparently did this to try to explain why he chose to be a Democrat instead of a Republican. Since he brought this up in his post I think he needs to clarify this timeframe to the voters.

Millholland ran as a democrat for 12 years, (no problem – own it), he then switched to an independent in 2015 BUT then in 2017 in his official role as the Sheriff he fully and enthusiastically endorsed and influenced voters to vote for Governor Ralph Northam and Attorney Gerenal Mark Herring. Actually Lenny probably pushed AG Herring over the winning line since he only won by 165 votes (or 85 swing votes) out on 2.2 million votes in the entire State. Life in Va has changed for the worse with many of his rulings since 2013 when Lenny first endorsed Herring.

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