Charles Lollar’s campaign imploding; Changes on the way?


There have been numerous signs of disarray in the campaign of Charles Lollar in recent weeks and months.

All the signs point to the disarray being a result of the mismanagement of the campaign by Lollar’s campaign manager, Karen Winterling. There had been rumors in the past that Winterling was on the way out, and I’ve also heard that she was originally supposed to leave after the kickoff tour but just couldn’t let go.

I’ve been told within the past few days that Karen Winterling is indeed on the way out the door now due to the campaign’s recent foundering. I’ve heard it could come as early as this week, if Lollar has the spine to actually fire anyone for a change.

Winterling’s business, Dealer’s Greatest Assets (DGA), paid at least two people who were travelling on the Lollar bus during the kickoff tour. One of those DGA employees was Jason Boisvert, whose primary election day activities in 2012 sent him to jail. Boisvert confirmed to me that DGA paid him the week that he was on the Lollar bus tour.

Additionally, the Lollar campaign has been using DGA facilities for campaign meetings. Are they running the whole campaign out of DGA’s office? Throw in that and the use of DGA employees on the bus tour and there are clearly some financial questions that need to be raised. Will the use of DGA offices and employees show up on Lollar’s campaign reports as an in-kind contribution? What other activities are being performed by DGA employees or happening using other DGA resources?

Lollar’s campaign office in Annapolis, with a big corner office for Winterling next to Lollar’s, is running behind schedule  for its opening. Why does a candidate even need a dedicated space in a campaign headquarters? Have a small office with a desk and a phone for interns, volunteers, or other staff to use and let the candidate use that when he’s in the office. No candidate should be spending much time at all sitting at a desk in an office. When candidates do, it should be only to have a place to sit and make personal fundraising appeals (and cell phones have made that less of an issue now.)

Of course, there have already been plenty of instances of proven mismanagement in the Lollar campaign.

Most recently, the Lollar campaign chose to totally skip the Maryland Republican Party’s Oktoberfest Saturday night. Both announced opponents (David Craig and Ron George) were there and one presumptive candidate (Larry Hogan) was also there. Their excuse – Lollar went to an event in Somerset County that started at 3. Lollar still could have conceivably made both events, but, even putting that aside, it’s no excuse for there being no stickers, signs, or volunteers for Lollar at the MD GOP event.  (Yes, I know he went to the Gaithersburg Oktoberfest Saturday as well but that would have been before headed to Somerset County since Gaithersburg Oktoberfest ended at 5 p.m.) Lollar also skipped the Prince George’s County Lincoln Day Dinner last week, while both the Craig and George campaigns had a presence there. Poor decision-making has reared its head in other issues for the Lollar campaign.

The campaign got off to a bumpy start on the kickoff tour when it was discovered the bus they were using had out of state tags. Regardless of why and any of the other spin on the issue, it’s not the image a credible campaign wants to put out there.

Then there was the issue with Lollar paying himself a salary on his failed Congressional campaign. Regardless of the Lollar response, you just need to look at the credibility issues all the other candidates who have done this, both here in Maryland and other states. It’s not something a candidate who wants to be taken seriously does.

Additionally, Lollar’s campaign recently admitted to not knowing when the Maryland State Education Association convention was, or even what the MSEA is. That’s not something a competent campaign staffer would tell a reporter. The Lollar campaign also recently sent out an email that was a graphic pasted into the body of the message with no actual text copy. This resulted in an untold amount of money being left on the table by the campaign because the donate links in the message were not clickable.

There have been other reports of disarray and people leaving the campaign. One was Mike Phillips, as previously reported by Red Maryland.

Here are some things Phillips said about the Lollar campaign from the Red Maryland story:

I resigned from the Lollar Campaign today. I can work with slimeballs called Democrats – but I can’t work with slime on my same team, mistreating volunteers – It was all I could do to keep from puking before I got out of the building where the campaign team meets. How Lollar handles this will determine whether or not he even still has my vote…and that’s not to say I want brought back in…Karen just needs to be handled. She does not represent the Charles Lollar people want elected and she will cost him the election.


In Short – Charles’ campaign manager does not represent who Charles is. I’m not sure Charles understands the depth of her lack of ethics and how she treats people.
As of today – 2 more people were fired – how do you fire volunteers? And one of those two men were doing the job they were asked to do. Karen took a man’s idea and ran with it but told the guy that Charles wanted on the campaign that we didn’t need him…of course Charles doesn’t know this yet – not that it would make a difference.
I’ve always known that politics was dirty and sometimes sleazy. I came in with eyes wide open. But never in a million years would I have thought that Charles Lollar would allow it to take place in his campaign, but when he refuses to listen to all those complaints he’s received, and all of the advice from friends now off and some still on the campaign – he keeps letting Karen Winterling act the way she does – it reflects on him.

Two days after Red Maryland reported on Phillips resigning the campaign, the Lollar camp put out a release implying he had been canned. That’s not really a surprise when you look at all the other mismanagement issues I’ve detailed and the personnel issues I’m about to detail.

Karen Winterling is apparently the cause of most of the problems the Lollar campaign is experiencing. It is unclear exactly how much aid her business is giving the campaign and whether that aid will be included on campaign finance reports.  This includes two people who her business, DGA, paid on the campaign’s bus tour as well as the use of meeting space.

Of course, a DGA employee and Lollar “volunteer”, Jason Boisvert, admitted that he was paid by DGA to be on the bus tour and I’ve heard he was one of the volunteers Winterling has reportedly mistreated. As you may recall, Boisvert was arrested and charged with interfering with an election official and not obeying a lawful order from law enforcement as well as other charges on primary day 2012. After being found guilty of assault and spending time in jail, he appealed and pleaded guilty to trespassing.

Winterling, who is the campaign manager, not just some low-level staffer or volunteer, recently devoted a large amount of time and energy to posting in various places online a call for people to vote in Red Maryland’s most recent online poll. Instead of just telling them to vote for Lollar she was also telling them to  vote “yes” on the question about whether candidates should draw a salary. All of this resulted in at least one post being made by a disgruntled Lollar supporter on the campaign Facebook page regarding this practice.

I’ve also been told by one GOP observer that, when it comes to politics, Winterling has a “black conservative fetish.”

Winterling and her employee Boisvert are not the only issues with the campaign personnel selection. Charlie had his Angels and it could be said that Charles Lollar has his Harpies.

Charles Lollar’s Harpies are Winterling, Julie Brewington, and Ginny Meerman.

Brewington is a county chair for the Lollar campaign and acts publicly on behalf of the campaign as well as online. She’s no shrinking violet and she lords overs the one Facebook group  for the Wicomico Society of Patriots she administers with an iron fist to make sure nothing the least bit negative gets said about Lollar. Additionally, she browbeats, threatens, and tries to shut up anyone who says anything she disagrees with. Because of one legal situation in which she dealt with one Salisbury blogger, Joe Albero, reportedly caused her to get a peace order against him she thinks she can hold legal threats (both criminal and civil) over the head of anyone who too vehemently disagrees with her in online arguments. She may want to check with a lawyer before she continues to spew this verbal diarrhea. I have shown that I am not intimidated by baseless legal threats on multiple occasions before. I did find this old article on Brewington cached online and I found it interesting reading.

Of course, while Brewington threatens anyone who disagrees her and makes all sorts of obnoxious and combative posts late at night  before later deleting them (hmm, I wonder why?), she isn’t above name-calling and invective herself. She implies Brian Griffiths has a mental illness just because he talked to the Baltimore Sun for a story. Her flunky on the Lollar campaign Matthew Adams also jumped in. Meerman, who has is also a county chair for Lollar, has made many over the top posts online about various subjects, some of them that aren’t that smart for someone trying to influence votes for Lollar.

I have just scratched surface of things I could talk about related to the Lollar campaign’s issues right now. I’m sure this will do enough to get the Harpies and the rest of the sorehead Lollar supporters online foaming at the mouth, so I’ll stop for now.

I expect to get hate mail and lawsuit threats. Be sure to send those messages to I’d also welcome any comment from Karen Winterling or anyone else with the Lollar campaign. I know they’ve been warned not to say anything bad about bloggers who write things they don’t like about the campaign, but, as Julie Brewington has proven, they aren’t always capable of following those instructions.

As I said before:

Most of the responsibility for the above mismanagement and lapses in judgement falls on Karen Winterling, the campaign manager.

A few months ago, Greg Kline  said that Lollar’s campaign “raises doubts in my mind that Mr. Lollar and his many loyal and hard working supporters really have an adequate understanding of the intricacies of running a statewide electoral campaign.  While Mr. Lollar is an intriguing candidate, I have to report my candid opinion that he does not seem ready to be a serious contender for the Office of Governor of Maryland.”

I would say the above assessment remains valid. Despite the enthusiasm and fervor of his supporters and the fact that Lollar is a dynamic speaker, he has to do something about his campaign structure so that it’s well-run in a professional manner. Otherwise, his credibility is going to continue to slide and his campaign will not be an effective one.

The Lollar campaign needs to make some staffing decisions that make it a professional and credible campaign. I don’t expect Lollar to drop out. I’ve heard from reliable sources that his pride and ego won’t allow that to happen. However, mistreating volunteers and abusing people online whose support you presumably would count on if your candidate were to somehow get the nomination is not a constructive process.

Many of Lollar’s activists point out they’d rather have a non-professional campaign, as a badge of their anti-establishment sentiment. However, having a campaign that’s such a disaster like the Lollar one is now is not anything to brag about. It is a sure sign of a campaign that will be circling the toilet bowl into last place on primary day in 2014 unless something is done soon. Lollar’s Harpies and others like them need be thanked for their past help and then put out to pasture.

Too many people in this situation are looking to get on a path to power themselves and the anti-establishment route is the way to get there (e.g. Jason Boisvert encouraged people to give to a Lollar moneybomb on Facebook so he could be “friends with an elected governor.) Can you imagine what would happen in a general election in Maryland with Lollar as the nominee and his Harpies and some of his other “volunteers” involved in his campaign? The media would have a field day.

I will continue to look into the Lollar campaign’s staff dysfunction as well as other topics related to how his campaign and personal finances , plus a look at some 1344.10 issues.

Jeff Quinton

Jeff Quinton

Jeff Quinton is an award-winning blogger who has been aggregating and blogging since 1998. He has worked as a reporter, in government, and as a communications professional in Columbia, SC and Washington, DC.

Quinton is a native South Carolinian who has lived in Baltimore since 2006. He is a recent convert to the Catholic Church and is active in the Knights of Columbus. He has been involved in the pro-life movement nationally and locally since 2010.

Quinton is a veteran who served as an intelligence analyst in the Army National Guard. He is also an Eagle Scout.
Jeff Quinton

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  1. Heard from who? I thought you weren’t talking to Mike Philips.

    With how much people are talking to you about me, you’d think *I* was running for office.

  2. To paraphrase Carly Simon, you’re so vain you even think this post is about you.

    This post is about the Lollar campaign and you’re just a bug on the windshield of the Edsel that is the Lollar campaign.

  3. You know, I was gonna explain that Facebook posting, but then I remembered that I named my blog “A Horrible Monster” for a reason.

    And it really seems that you’ll go after anything, including Facebook postings, from anyone associated with the campaign in the old Leftist trick of taking anything and trying to kill the opposition.

    So bias, blah blah, agenda, blah blah.

    Just… why?

  4. And you’re here reading every bit of it (along with lots of other people) and declaring yourself a “minor celebrity” over it.

    It’s pretty funny that all you’ve got is accusing me of a leftist trick and name-calling. That’s another leftist trick to use when the truth isn’t on your side. No comment on this whole story? Like I said, you’re just the turd in the punchbowl at a very disorganized large dinner party that is the Lollar campain. What do you think of the whole dinner party as written above?

  5. Dude, you *named* me. You can’t pretend this isn’t about me, at least in part.

    For the record, you named Winterling 13 times in direct reference, Lollar ~10 times in direct references to the man, and me 6 times.

    To name me that often, to the point of including the summary of your previous article on me, and then claim this isn’t related to me is ridiculous. *You* decided to make me part of The Main Event when you could’ve left me out, but so far, you keep plugging my name into your attack articles on Lollar (I’ve noticed that you’ve picked up the torch that The Unprofessional and Unserious Brian Griffiths had to abandon after making potentially defamatory statements about Lollar). You don’t have to include me, but you *single me out by name* and expect me to what? Run away? Shut up?

    I spent five months in jail for trying to stand against corruption. If that is your goal, you need to re-evaluate.

  6. I told you in the very beginning I was a nobody, and warned you in advance that you’d be disappointed. So here’s the disappointment: I’m not high enough in the campaign to know whether your source has his head screwed on straight. I can’t confirm whether your rumors have any basis in reality.

    I do, however, doubt it. Politics is bloodsport after all, and unnamed sources are the traditional go-to for spreading mischief.

    You know I was reading your blog for about a month before I posted and thought you were a pretty decent guy? Then I commented (Negatively, to be fair) on a post you made and you went after me. This is how you treat your readers? Be careful, ladies and gentlemen of the audience, disagree with your host and he will make every effort to go after you personally, if I am any example.

  7. Oh hi Brian, I thought I wasn’t relevant. 🙂

    “Obsession” is a word that is over-strong. I just find it interesting that a friend of yours picked up your entire line of attack against someone after you dropped it is all.

    But hey, if it makes you feel important, roll with it.

  8. […] Aside from the laughable “robust organization” comment, the fact that Lollar tried to change the subject and declined to say whether Karen Winterling is still “on the job” shows that things aren’t as rosy as Lollar and his partisans are trying to make them out to be. Is Lollar looking for a new campaign manger? Will Winterling be fired or reassigned? If that ends up being the case, remember where you heard it first. […]