Democratic Dilemma

Steven Leibowitz
4 min readJun 11, 2024


In 2018, I ran and failed to unseat a Republican incumbent for the First Barnstable State Representative seat. No regrets, I am glad I had a chance to raise many important issues and appreciate the support I received. That day has come and gone for me, I’m more interested in raising up people who have the same core values I still have. Government should reflect the best of us.

In 2022, the seat opened up and sure, I was thinking about it. On Columbus Day weekend, I sat down with another potential candidate, then Dennis Select Board member Chris Flanagan. I spoke pretty openly about what I learned from 2018 and that the Democrats should avoid a primary and that there was someone else whom I thought would be pretty viable, that person should be in the discussion also.

The following Tuesday, having said nothing to me, Chris took out papers to run. I said nothing publicly at the time, but in hindsight see a connection to future events.

Chris won the seat by a couple thousand votes, doing significantly better in my own town of Brewster, than his of Dennis. We were amicable, I work on a lot of issues still and want my state rep on board. I did not see him as setting the world on fire up there, but I figured ok, first term. Though several times he would say let’s do coffee, but that never happened. And he seemed very reluctant to co-sponsor legislation. I consider myself fairly progressive and Chris co-sponsored relatively few of the bills Progressive Mass deemed important, his voting record slightly better than the average Democrat.

In April, The Commonwealth Beacon reported that Rep Flanagan had been the focus of a lengthy investigation that revealed he sent out a mailer under the guise of Conservatives for Flanagan to Dennis voters. A complaint was filed to the MA Office of Campaign and Political Finance (OCPF)after the election. OCPF attempted to determine who authorized and paid for this political mailing. Rep. Flanagan was not responsive to OCPF, who even had to threaten it would be referred the Attorney General’s office unless he spoke to them. Rep. Flanagan told OCPF he met this person a campaign event who said she wanted to help and that this person “Jean Louise”, whom he had no other information about, coordinated the mailer.

As Flanagan stuck to the story, even describing Jean Luise, OCPF attempted to locate this person. Flanagan finally admitted he lied to OCPF and this person did not exist.

As you can imagine, OCPF was not happy and in a six page letter summarizing the events, levied nearly $40,000 in penalties to Flanagan and the campaign. The Speaker of the House used harsh language in describing his reaction to this. House Republicans may attempt to bring this to the Ethics Committee.

Ironically, the Republicans had not fielded a candidate to run against Flanagan, and had no time to do so when this broke. They are supposedly trying to find someone to run as write-in for the September primary and if that person receives 150 votes, would appear on the November ballot. I cannot imagine they won’t field someone and it will be months of voters hearing about this.

After all these fines, Flanagan has a paltry less than $2,000 in the bank, a startling low amount and reluctant activists willing to donate. I found it odd, again in hindsight, that Flanagan had a fundraiser in Late March, shortly before this was all public, but surely he was aware of what was coming. I remarked to people that he had even referenced that the Republicans might run a write in candidate. It made me think he needed to raise money because of what was coming from OCPF and before people knew.

The email Flanagan sent out to his email list after this came out was less than helpful. He called this incident a “mistake”. If I have a typo in this article, that is a mistake. OCPF was clear that intentional acts of deception were conducted. An attempt to underplay this, falls flat.

Flanagan has met with the Dennis and Brewster Democratic Town Committees. There remains among these most active of people, a significant amount of anger and disappointment. I am certainly among those.

You see, not only do Democrats on Cape Cod have to worry about this seat, presumably, but supporting Flanagan cedes any high moral ground across the region. I am disappointed at the silence of other elected Democrats. Doing so simply invites questioning their silence and whether they hold two moral standards. It is exactly why people are cynical about politics.

Unfortunately, it does not seem the local Democrats have a deep bench that anyone would have decided to run what would be a difficult primary write in campaign against Flanagan. But that is just a guess that it would be difficult, I can’t imagine voters wanting to support someone that consciously deceived them and the state agency in charge of reviewing campaigns. But I would find it easy to support a different Democrat.

Flanagan could have taken his name off the ballot by May 31. Obviously, he thinks he can ride this out. At the meeting with the Brewster Dems, he mentioned not being able to answer some questions because of potential litigation that might occur. Oh great.

So here we are. Is Flanagan permanently damaged goods with voters and in the House? Personally, it would take a long time and significant effort on many fronts to feel comfortable. If there is a Democrat out there that is thinking, we deserve better than to deal with this, there will be people that will take that ride with you.

Like I said, we deserve a government and elected leaders that reflect the best of us.



Steven Leibowitz

I dabble with things. Easily amused, sometimes amusing. Trying to heal the world.