My name is Bobby O’Shea, and I am honored to be a candidate in the 2025 Annapolis mayoral race.
I recognize that I entered this race late, filing on July 15th, and my name may not be as recognizable as my opponent’s — but my love for this city is unparalleled. My decision to run was driven by my opponent’s silence on recent events that deeply concern me and many residents of our city. I am reaching out to voters, sharing my concerns, and asking for their support as I work to earn their trust and their vote.
One catalyst for my campaign was the city’s decision to demolish the Harbormaster Building. After Historic Annapolis filed an appeal challenging the approval process for the new Maritime Welcome Center — which lacked secured funding or federal grants — the city proceeded to tear down the building without awaiting the court’s response. This move appears designed to force the construction of an overpriced modern glass structure that clashes with the historic character of City Dock.
More importantly, without funding in hand, taxpayers could be left on the hook for the cost. Since its destruction six months ago, the city has had no public restrooms, broken roadways, lost parking spaces, and no rebuilding. Because of this, our local businesses are suffering. My opponent remained silent.
The citizens of Annapolis have come out in force against a high influx of short-term rentals (STRs), high-density housing, neighborhood zoning changes, the ban on drive-thrus, and a height variance for a proposed hotel at City Dock. Downtown parking and garages are a nightmare for residents and tourists alike.
Our fire department is pleading for an additional rescue unit to address critical coverage gaps. Our police department is understaffed and underfunded. Residents in public housing are living in mold- and roach-infested apartments and have been forced to sue the city to demand action.
My opponent remains silent on these issues.
“If silence is consent,” then my opponent has agreed with the failed policies of Mayor Buckley and wants to preserve the status quo. I want to be the voice of the people and deliver the change our city so desperately needs.
As your mayor, my main objectives will be to:
• Enhance public safety
• Reduce excessive taxes and fees
• Ensure our city’s infrastructure meets the highest standards
• Improve living conditions in public housing
• Address downtown flood mitigation by maintaining the pumps and untethering their funding from the Maritime Welcome Center
Every Annapolis family deserves safe neighborhoods. Parents should feel confident that their kids can walk to school or play outside without fear. My administration will partner with police, fire, and EMS to cut crime, strengthen community policing, and build trust with residents — ensuring everyone, especially children, enjoys public spaces worry-free.
Annapolis residents face a high tax burden following a 10% property tax increase. I’m committed to cutting it to 2% — matching the county rate — to deliver relief for homeowners and keep our city affordable.
As mayor, I’ll cut $20 million from the city budget: $10 million in direct savings and $10 million reallocated to police, fire, EMS, and proactive maintenance. I will meet with the county executive to discuss opportunities for shared services that result in additional savings while ensuring high-quality services without placing undue burden on residents.
Our streets, sidewalks, and parks affect us daily. As mayor, I will shift from reactive repairs to proactive maintenance of all city infrastructure. Routine upkeep will prevent costly fixes, keep public spaces in top shape, boost quality of life, support businesses, and build community pride.
I will also partner with residents of Public and Section 8 housing to protect our most vulnerable citizens. Their voices will be heard, their pleas answered, and poor living conditions won’t be tolerated. We’ll hold property owners accountable to ensure every Annapolitan has a safe, livable home.
These priorities, shaped by the needs and expectations of Annapolis residents, will build a safer, more equitable, and well-maintained city. Residents deserve confidence that their voices matter and that government serves them.
Together, we will advance community-driven initiatives to enhance life for all in Annapolis.
My name is Bobby O’Shea, and I’m asking for your vote on Tuesday, November 4th, for Mayor. Together, we can make a real difference in the city we call home.
https://www.eyeonannapolis.net/2025/11/opinion-my-commitment-to-responsible-leadership/
About the Author
