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Annapolis 2025 voter guide: Bobby O’Shea, candidate for Mayor of Annapolis

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Bobby O’Shea

Candidate in Nov. 4 general election Republican Murray Hill

Age: 66 on day of General Election (Nov. 4)

 

Occupation: Business Consultant to the Defense and Medical Industry

 

Education: Canandaigua Academy

 

Previous political experience: Ran in the Annapolis Mayoral and House of Delegate 30A as Candidate

Why are you running for office?

Annapolis needs a mayor who will listen to the residents’ concerns and values. A mayor who will put the city’s needs over his own personal gain. Annapolis needs a mayor whose vision fits the character of our great community and establishes a path forward that fits this unique place we call home. That’s me! I will work to gain the trust of the public and create a city that all will be proud of. Every neighborhood has its own character, history, and goals. My administration will respect and preserve it. I will establish rapport with community leaders and receive input on their vision moving forward to better their neighborhood for all involved. As mayor, I will be Transparent, Accessible and Accountable for all.

Gun violence has been on a downward trend since 2023. What is your plan to keep that trend?

Some studies indeed report a downward trend in gun violence since 2023, returning to pre-pandemic levels. The problem lies in varying methodology. Data excluded in one study may be recorded in another, leading to different interpretations. An example would be shots fired, a crisis across our city. While some incidents of violence are trending down, through Aug. 20, incidents involving homicide, shootings, or shots fired were up 54% year over year, from 24 to 37, according to the city’s Annapolis Homicide & Gun Violence Dashboard. My administration will host regular community walks and resident listening sessions to build trust. Mentorships and after-school programs will be two of the avenues I plan to implement to promote prevention. Creating hot-spot foot patrols and working closely with prosecutors and probation officers to identify repeat violent offenders. Every neighborhood has a right to safety. As mayor, I will report all data honestly, invest in prevention, and have a visible, respectful police presence that reduces crime and protects residents.

The spending plan for the city has increased its operating expenses by roughly $17.2 million since fiscal year 2024. Do you believe the city is spending too much? Why or why not?

Yes. Annapolis is overspending. The budget has risen from 106 million in 2017 to nearly 200 million today. Public safety is underfunded. Our streets are lined with potholes and unfinished bike lanes. Our kids play on fields that turn to mud after rain. The pumps downtown have not been maintained. Too many dollars are tied up in administrative layers and redundancy, not in neighborhood needs. As mayor, I will freeze non-essential administrative growth and conduct a top-to-bottom efficiency audit. Then redirect the savings to paving, parks, stormwater, and facility upkeep. My vision will move from reactive repairs to a proactive schedule with clear timelines. My administration will hold the line on taxes by controlling overhead and prioritizing core services first. Annapolis residents deserve visible, reliable results for every tax dollar. As mayor, I will cut waste and invest in maintenance, prevention, and community needs. I will reduce the budget for the residents who fund it.

Many Annapolis residents are concerned about the affordability of living in Annapolis and several city council candidates want to improve affordable housing in the city. What do you plan to do to address this? What are your thoughts on the city’s current property tax rates?

The city’s property tax is excessive. I support a maximum 2% assessment rate of increase for the Homestead Property Tax Credit. I am the only candidate who supports a property tax cap. Housing is affordable when the tax burden no longer cripples the homeowner. My administration will protect generational homes through property tax freezes or assessment increase limits. Less than 10% of the city is undeveloped. I’ll protect that asset. I oppose high-density development that diminishes our quality of life. I will not allow development that overburdens our schools and infrastructure. As mayor, I’ll establish a registry of abandoned and neglected properties, create public-private partnerships to transform them into unique and affordable homes. Reduce permit fees on ADUS and first-time homeowners restoring properties. I’ll enforce inspections for public housing. Establish a “quality of life” for all the rentals. It does not matter if the home is affordable if it is not livable.


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The Capital Gazette’s voter guide allows candidates to provide their background, policy and platforms on issues, in their own words. Any questions or feedback can be emailed to elections@baltsun.com, or read more about the questionnaire process.

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