May 30, 2024
Annapolis, US 57 F

Crystal Balling the Annapolis City Election–Our Predictions

Over the past few months, people have asked my predictions on the Annapolis City elections.  Eye On Annapolis has never done endorsements in any race; however, predictions are another story.

This year is a strange election with little civic involvement and to be honest a very boring slate of races. With mail-in voting, we will likely not know the official winners in any race until November 9, 2021.

With that said, here are my predictions (winners in bold) and reasoning for each of the races.

Ward One

Elly Tierney (D). Elly is running unopposed and to be honest, served her constituents very well over the past four years. She even sold her business (a bed and breakfast) to advocate for her constituents. That may not have been the only reason, but it was one. Look for Elly to make a run for Mayor in 2025.

Ward Two

Scott Gibson and Karma O’Neill (D). This will be a tight race and the residents of Ward Two would be ably served by either candidate. I believe this is going to come down to voter registration and the democrats far outnumber the republicans in this ward. Yes, the ward was represented by Alderman Paone (a republican) for many years, but over the past two election cycles, he faced credible threats from democrat Kurt Reigel. The demographics have changed and new families have moved into the area and I believe Karma O’Neill will win this office.

Ward Three

Rhonda Pindell-Charles (D). Rhonda is running unopposed and will obviously win this race. She has ably represented the ward since the retirement of Classie Hoyle and has incredibly deep roots in the community. I am constantly impressed with her ability to reason every side of an issue and the depth of her knowledge of the issues. I was surprised that her primary challenger, Keanuu Smith-Brown did not do better; and I honestly thought the youth vote might have a shot at winning that race, but Pindell-Charles won in a landslide.

Ward Four

Sheila Finlayson and Toni Strong-Pratt (D). This may be one of the upsets we see. Strong-Pratt ran against Finlayson in the primaries of 2017 and 2021 and after narrowly losing both times mounted a write-in campaign. She lost the primary by only 5 votes and that is a tight margin. Stong-Pratt seems determined to get this seat and I suspect she found the votes to win the election. With that said, write-ins can be tricky and depending on how technical the Election Board wants to be, it could go to Finlayson.

Ward Five

Brooks Schandelmeier (D) and Monica Manthey. Schandelmeier is a political machine and a fundraising machine and likely will not be in local Annapolis politics for too long. He has represented the ward well after being appointed to the seat earlier in the year and will handily win his first election. His opponent, Monica Manthey just moved to the area and entered the race very late in the game as the republican central committee struggled to find candidates. With Annapolis (and the ward) favoring democrats, her attendance at the January 6th rally to support former President Trump certainly did not help her case.

Ward Six

DaJuan Gay (D) and George Gallagher.  This will be a historic race I believe. Gay raised zero dollars for this race and spent zero dollars. He quietly campaigned among his constituents and I believe he will win in a landslide. His opponent, George Gallagher ran against Gay in the special election in 2019 and lost.  And while we are not sure what Gay’s platform might be, we do know that Gallagher’s is basically “Gay stinks” and a bunch of hashtags vomited over social media.

Ward Seven

Rob Savidge (D). Savidge is running unopposed.  Savidge represented his ward well for the past four years despite having a nearly singular focus on the environment–not that that is bad. He is the perpetual environmental voice on the council with a green focus that will serve the City well.  Like Tierney, I would not be surprised to see Savidge toss his hat into the Mayor’s race in 2025.

Ward Eight

Ross Arnett (D) and Rock Toews (R). Like ward two, this will be a close race. Alderman Arnett drew a primary opponent in Kati George who did very well and had the support of Mayor Buckley. I suspect that many of her supporters will either slide to the republican side or sit the election out and give the slight advantage to Toews. This is very similar to when former Mayor Cohen drew a primary challenger and ended up losing to former Mayor Pantelides.


Gavin Buckley (D) and Steven Strawn (R). Buckley has served the city well over the past four years despite several missteps. He promised to not raise taxes and he did. The stopping of inspections at HACA properties. And then that whole bike lane thing. He has learned to be a politician in the past four years and I am not sure if that is a good thing or not. Like prior Mayors before him, he blamed his predecessor for the inflated budget. And like his predecessors, he switched up the way the budget is done so there can not be a valid comparison.  However, there have been a number of successes including expanding the biking trails, additional recreation opportunities, improvement over bond ratings (although they are not a real good indicator of much), and perhaps most significantly starting the process to re-build HIllman garage and re-develop City Dock including the establishment of the resilience authority.

His opponent, Strawn, disclosed to The Capital in his first interview that he did not want to run and he was only there because no one else filed. And throughout the campaign, refused to participate in most voter-information opportunities. Like Gallagher in ward six, the bulk of his platform was “Buckley stinks” without offering any substantive message about why he would be the better choice.

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