Eastern Shore Undercover Endorsement for Wicomico County Council District 2

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October 26, 2026

In the Wicomico County Council District 2, we have Mr. James Winn, who is a Republican and currently sits on the council, running against Jim Adkins, a Democrat, in the general election on November 3, 2026.

First, let's start by looking at Mr. Winn. I sat down and looked at the votes Mr. Winn has cast and the decisions he has made. From my view, he has been very reasonable, Not only with his votes, but also with his public comment at each council meeting.

He does not just go along with the group on every topic, and I think that is very important. We don't want constant bickering but we also don't want council members who are just going to agree and go along with the crowd.

Mr. Winn sees both sides of an issue. He thinks about what is best for the community before he votes. That matters on a council that often votes the same way.

One example is the Lord's Prayer. When the council removed it from meetings, Mr. Winn spoke up. The easy move was to go along with the others and avoid trouble, but he did not do that.

During that conversation, we had several people message us and explain they were not happy with the Lord's Prayer being removed from the council meeting. Our recommendation was to reach out to the council members and express their displeasure about what was happening.

I personally know of several people that reached out to Mr. Winn. Mr. Winn defended the community's voice, which is what should always happen.

Mr. Winn believed many people in Wicomico County liked having the prayer at council meetings. He stood his ground, and some people tried to put him down for it. I have come to know him as a very faithful man and in my opinion, handled the situation professionally and accordingly.

Another example is the vote on two extra county employee holidays in February 2024. Mr. Winn explained that the holidays were already planned for and the money was already in the current budget. That meant no extra cost to taxpayers, and it showed thanks and appreciation to hard working county employees.

This should have been an easy decision. Some council members still debated it and did not want employees to get the extra holiday at Christmas time. Mr. Winn used common sense, which I would think most leaders would in that situation knowing it wasn't going to cost taxpayers any additional money, but that just wasn't the case.

Then there is the legal fight from November 2023. The council and the County Executive's office went to court against each other. The council spent somewhere between $50,000 and $60,000 on legal fees, and taxpayers paid that bill.

The council wanted to keep fighting to get a win and spend even more. Mr. Winn objected to that. In my opinion, he has been on an island by himself, because most of the council has been against the County Executive and let personal feelings drive their decisions.

Mr. Winn has not gone down that road. I am sure he has disagreed with the County Executive at times. They are both professional, and he has not let that get in the way of his decisions.

Now let's talk about Mr. Adkins. I believe a vote for Jim Adkins is a vote to keep the same council we have now. I encourage you to go to the PAC 14 videos from the last four years and listen to any one of the public comment sections.

Mr. Adkins has been very vocal in his complaints about County Executive Julie Giordano. He has complained about many things she has done, and it has gotten harsher with each council meeting.

At this point, it's certainly much more than just a disagreement, it's become a personal issue and vendetta against the county executive.

The past four years have shown what happens when county leaders focus on fighting each other instead of governing and working together for the Citizens of Wicomico County. Projects get delayed and budgets turn into battles. Public trust drops and staff morale suffers.

Residents are the ones left waiting. They just want their roads fixed, their services delivered and their tax dollars spent wisely. Meanwhile, the arguing goes on about who is right and who gets to put a chalk mark on the win/loss column.

Mr. Adkins has shown us, publicly and often, how he views the County Executive and her office. I do not see a reasonable way that electing him would lead to a county government that works better together and cohesively. I believe it would bring more of the same, if not worse.

That means more grandstanding and more roadblocks on routine work. It means more wasted council sessions, while citizens watch their elected officials perform for social media and podcast audiences instead of serving the public.

Mr. Adkins has also been a vocal opponent of the Barren Creek Road project. Many people may not know that he lives on that street. For many years, that road has been a long driveway for Mr. Adkins and his family. But many others in that area use that road and believe it should be rebuilt.

By now, I'm pretty sure you know who I am going to recommend. I believe James Winn is the best choice for this seat. He has shown he can work with the County Executive and with other council members, and he can steer the council in the right direction for the citizens of Wicomico County.

Eastern Shore Undercover proudly endorses James Winn for Wicomico County Council District 2.