Sheriff endorsement photo

Former Frederick County Sheriff Robert Williamson (left) is endorsing Allen Sibert for sheriff in the Nov. 5 election, despite supporting current Sheriff Lenny Millholland in the 2015 election.

WINCHESTER — Former Frederick County Sheriff Robert T. Williamson has endorsed Winchester Sheriff’s Office Maj. and Chief Deputy Allen Sibert for county sheriff in the Nov. 5 election.

Sibert, the Republican nominee, is challenging incumbent Sheriff Lenny Millholland, who is running for a second four-year term as an independent.

Williamson served as the county’s sheriff from 1992 until his retirement in 2015.

In the November 2015 election, Williamson, a Republican, endorsed Millholland over Republican candidate Terry Bohan, saying he believed Millholland had a better knowledge of the community and the Sheriff’s Office.

But a Friday post on Sibert’s campaign Facebook page showed that Millholland has lost Williamson’s support.

“I’m endorsing Allen Sibert because he is who is needed for the challenges our county faces,” Williamson said in the post. “I believe in Allen, his vision and ability to lead is why I brought him to Frederick County. I supported Lenny in 2015, but he has not lived up to the expectations that the Sheriff’s Office needs. I truly believe Allen is the effective manager we need now.”

“It’s a phenomenal endorsement which is just one of many to come,” Sibert said in a phone interview. “I’m very humbled to get Sheriff Williamson’s endorsement. I can’t say enough and I can’t thank him enough for supporting me. It sends the message that I am the leader that the Frederick County Sheriff’s Office needs.”

Williamson could not be reached for further comment.

Over the weekend, Sibert also was endorsed by Winchester Sheriff Les Taylor, who is his boss.

— Contact Josh Janney at

(11) comments


What is the largest financial budget that Mr. Sibert has managed during his 29+ years in law enforcement and where was that?

Also, during Mr. Sibert's law enforcement career, what is the largest number of associates that has been under his supervision and where was that?


In reference to the military vehicles ask Lenny to go on camera saying the vehicles were not "quickly" repaired for the video. The few vehicles he showed were only a few of the 2.8 million he said he received. I wish the VSP (since they are the official monitoring agency) would inventory all the items he received from the military to see if they are still there.

Gary Williams

I never thought I’d see corruption in Frederick County politics. Folks, it is here. Former Sheriff Bob Williamson has endorsed Al Sibert for Frederick County Sheriff. Sibert is seeking to be Sheriff of a department he was once asked to resign from, under former Sheriff Williamson. Williamson has made a mockery of his oath of office. Can Al Sibert really be trusted to manage a $15 million budget?

I’ve known Lenny Millholland since he was a rookie Officer with the City of Winchester Police Department. He has always upheld and enforced the law fairly. His integrity and commitment to his community are exemplary. Let’s continue his record of trust and Re-Elect Sheriff Millholland. And also, show this to your neighbor and ask them to vote for Sheriff Millholland.


Corruption?, Really? Why don't you just say my wife is Lenny's secretary and she doesn't want things to change.


Gary weren't you asked to resign or were you fired by Sheriff Williamson, sour grapes.


I don't know either one personally. I would like to see a comparison of law enforcement training and investigation experiences--a resume of sorts.


Mr. Sibert has much of his training and assignments on his Facebook Page - Sibert for Frederick County Sheriff and on his website he is very transparent.


Someone probably tried to share it in your group but you disagreed and banned them!


I don't know Mr Sibert other than from the previous article with him bashing Sheriff Milholland over the military equipment the county received.Disasters happen and being prepared for anything is important.As for the equipment being worn out,the military follows a strict maintenance schedule and yes they are going to need repairs like any other vehicle but these vehicles may save someone life some day so how about you tell is what you bring to the table and not rely on bashing your opponent to make yourself look good.

As for Kenny Milholland,I don't live in the area anymore but during a tragic family event my family got to know Lenny when he was a detective with the City and I can tell you that he is an honest man that truly cares about people.Let's all remember that we are voting for the man not who endorses them.

Steve Cunningham

It has been 25 years ago when Kenny was a detective and things change over time. You are bashing Al over one video, but all of his videos are telling what he brings to the table, you need to take the time to watch all of his videos so that you are well informed especially since you 'don't live in the area anymore'


Who is this Kenny you speak of. His name is Lenny. Lennard If you want to see the vein bulge in his forehead.

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