Annapolis City Council Aldermanic Candidate Profile: Jack Papaleonti, Ward 5

Report Annapolis News has asked various candidates currently seeking office on the Annapolis City Council to participate in a question and answer profile ahead of the general election on Tuesday, Nov. 4, 2025. In this profile, our readers are introduced to Jack Papaleonti, Ward 5 Aldermanic Candidate.

Email Address: jack@academyrealty.com
P.O. Box 6519, Annapolis, MD 21401

Mailing Address: P.O. Box 6519, Annapolis, MD 21401

Vision and Priorities

What is your long-term vision for Annapolis, and how will you address its main challenges and opportunities, particularly regarding City Dock redevelopment?

My long-term vision for Annapolis is to preserve the charm, history, and waterfront character that make our city so special while ensuring it remains a safe, thriving, and financially responsible place to live, work, and visit. The City Dock redevelopment is an opportunity to protect our waterfront from flooding and improve public spaces, but it must be done carefully—with fiscal discipline, respect for small businesses, and a focus on maintaining our historic identity as a boating and maritime community.

What are the most important issues facing Annapolis residents, and how will you prioritize them?
Public safety, fiscal responsibility, infrastructure, and maintaining the city’s character are my top priorities. We must ensure our police and fire departments are fully staffed and equipped, that taxpayer money is spent wisely, and that development enhances—not erodes—our small-town charm.

If elected/re-elected, what would you aim to achieve in your first six months on the council?
In my first six months, I’ll focus on building strong relationships with the Mayor, Council, and department heads, while meeting with residents and business owners in Ward 5 to understand their priorities. I’ll also review the city’s budget closely to identify areas where spending can be better managed or redirected toward public safety and essential services.

How will you improve the quality of life for residents and their families?
By ensuring safe neighborhoods, well-maintained parks, responsible growth, and efficient city services. Families should feel secure and proud to call Annapolis home. I’ll advocate for balanced budgeting that supports core services while protecting taxpayers.

How will you prioritize improving the quality of life for marginalized communities?
Every resident deserves to feel valued and heard. I’ll work to ensure city resources are allocated fairly, focusing on safety, education, and access to opportunities for all neighborhoods. A strong, united community benefits everyone.

What action will you take to address concerns related to reparative justice and creating an Office of Freedmen Affairs?
I believe history should be remembered and respected, and that all communities deserve equal access to opportunity. I’d want to fully understand the fiscal impact and purpose of any new office before supporting it. My focus will remain on fairness, equal treatment, and using taxpayer dollars responsibly.


Local Issues and Policy

What are your solutions for housing affordability, including homeownership, rental costs, and workforce housing?
We need to encourage responsible development that fits within our infrastructure, supports workforce housing, and protects existing neighborhoods. As a Realtor, I understand the importance of balancing supply and demand. Streamlining permitting, encouraging mixed-use projects, and maintaining reasonable taxes can all help make housing more attainable.


Transportation and Parking

Given traffic congestion and limited parking, how will you improve public transportation and address downtown parking issues?
We need common-sense solutions—such as better use of existing parking garages, improved signage, and stronger partnerships with private parking providers. I support exploring shuttle systems and better transit links from outer lots to downtown, especially during peak tourism seasons. The goal is to keep traffic moving while making downtown accessible for residents, workers, and visitors.


Public Safety

What is your philosophy on public safety, and how will you address growing crime and concerns with police transparency and accountability, while also promoting community well-being?
Public safety must be our top priority. That starts with supporting our police officers and firefighters through competitive pay, proper training, and strong leadership. Transparency and accountability are essential, but so is morale. We need to build trust between first responders and the community—rooted in respect and communication.

What will you do to address the critical shortages of emergency personnel and lifesaving equipment within the fire department, as recently expressed by the Annapolis Professional Firefighters union?
I support ensuring the Fire Department is staffed and equipped to meet NFPA 1710 standards. That means looking closely at the budget to identify where funds can be reallocated and determining whether proper staffing can reduce costly overtime. I have full confidence in Chief Remaley’s leadership and believe promoting from within helps maintain a strong culture of professionalism and pride.


Environment and Resiliency

As a coastal city prone to flooding, what are your plans for environmental protection, climate change resiliency, and stormwater management?
We need practical, science-based solutions to manage flooding and protect our waterfront. That means maintaining storm drains, investing in infrastructure upgrades, and ensuring redevelopment projects include strong flood mitigation measures. Protecting our environment goes hand-in-hand with protecting property values and public safety.


Economic Health and Small Business

What strategies do you propose to help Annapolis businesses thrive, especially small businesses?
As a small business owner myself, I know the challenges local entrepreneurs face. The city should streamline permits, reduce unnecessary regulations, and make it easier for businesses to operate. We should also promote tourism and local events that drive foot traffic while maintaining the character that makes Annapolis a destination.


Collaboration and Governance

How will you handle controversial issues, especially if the council is divided?
I believe in respectful debate and fact-based decision-making. I’ll listen to all sides, seek common ground, and make decisions that serve the city’s long-term best interests—not short-term politics.

What is your approach to collaborating with other council members, and state and county agencies, to achieve city goals?
Collaboration is key. I’ll maintain open communication and look for partnerships that benefit our residents—especially in areas like transportation, education, and public safety. Effective government depends on teamwork and shared goals.

How will you balance the needs of your ward's residents with the city's overall interests?
Ward 5 will always be my first responsibility, but what’s best for the ward often aligns with what’s best for the city. I’ll advocate strongly for my constituents while keeping an eye on the broader health and sustainability of Annapolis.

How will you manage public criticism as a City Council member?
By listening respectfully, staying transparent, and focusing on facts. Constructive criticism is part of leadership. I’ll stay grounded in my values and decisions I can defend with integrity.


Experience and Community Engagement

Describe your plan to work with and engage community stakeholders (residents, businesses, non-profits).
I’ll continue building relationships with local organizations, businesses, and civic groups. My involvement in the Annapolis Optimist Club has shown me the value of community partnerships. Listening, showing up, and being accessible will guide how I lead.

How will you engage with and gather feedback from residents, particularly those who feel disconnected from the city council and various departments across the city government?
Communication is key. I’ll hold regular town hall meetings, maintain an active online presence, and make myself available to residents. People should feel their voices matter—and that their elected officials are listening.

How do you plan to manage the significant time commitment of City Council duties alongside other obligations?
I’ve built my business on organization, discipline, and time management. I’ll dedicate the time necessary to serve effectively and responsibly represent Ward 5.

What values will guide your decisions as a council member?
Integrity, accountability, fiscal responsibility, and community. I believe in protecting public safety, supporting small businesses, respecting taxpayer dollars, and preserving the historic, small-town character that makes Annapolis the place we all love to call home.

Vision and Priorities

What is your long-term vision for Annapolis, and how will you address its main challenges and opportunities, particularly regarding City Dock redevelopment?
My long-term vision for Annapolis is to preserve the charm, history, and waterfront character that make our city so special while ensuring it remains a safe, thriving, and financially responsible place to live, work, and visit. The City Dock redevelopment is an opportunity to protect our waterfront from flooding and improve public spaces, but it must be done carefully—with fiscal discipline, respect for small businesses, and a focus on maintaining our historic identity as a boating and maritime community.

What are the most important issues facing Annapolis residents, and how will you prioritize them?
Public safety, fiscal responsibility, infrastructure, and maintaining the city’s character are my top priorities. We must ensure our police and fire departments are fully staffed and equipped, that taxpayer money is spent wisely, and that development enhances—not erodes—our small-town charm.

If elected/re-elected, what would you aim to achieve in your first six months on the council?
In my first six months, I’ll focus on building strong relationships with the Mayor, Council, and department heads, while meeting with residents and business owners in Ward 5 to understand their priorities. I’ll also review the city’s budget closely to identify areas where spending can be better managed or redirected toward public safety and essential services.

How will you improve the quality of life for residents and their families?
By ensuring safe neighborhoods, well-maintained parks, responsible growth, and efficient city services. Families should feel secure and proud to call Annapolis home. I’ll advocate for balanced budgeting that supports core services while protecting taxpayers.

How will you prioritize improving the quality of life for marginalized communities?
Every resident deserves to feel valued and heard. I’ll work to ensure city resources are allocated fairly, focusing on safety, education, and access to opportunities for all neighborhoods. A strong, united community benefits everyone.

What action will you take to address concerns related to reparative justice and creating an Office of Freedmen Affairs?
I believe history should be remembered and respected, and that all communities deserve equal access to opportunity. I’d want to fully understand the fiscal impact and purpose of any new office before supporting it. My focus will remain on fairness, equal treatment, and using taxpayer dollars responsibly.


Local Issues and Policy

What are your solutions for housing affordability, including homeownership, rental costs, and workforce housing?
We need to encourage responsible development that fits within our infrastructure, supports workforce housing, and protects existing neighborhoods. As a Realtor, I understand the importance of balancing supply and demand. Streamlining permitting, encouraging mixed-use projects, and maintaining reasonable taxes can all help make housing more attainable.


Transportation and Parking

Given traffic congestion and limited parking, how will you improve public transportation and address downtown parking issues?
We need common-sense solutions—such as better use of existing parking garages, improved signage, and stronger partnerships with private parking providers. I support exploring shuttle systems and better transit links from outer lots to downtown, especially during peak tourism seasons. The goal is to keep traffic moving while making downtown accessible for residents, workers, and visitors.


Public Safety

What is your philosophy on public safety, and how will you address growing crime and concerns with police transparency and accountability, while also promoting community well-being?
Public safety must be our top priority. That starts with supporting our police officers and firefighters through competitive pay, proper training, and strong leadership. Transparency and accountability are essential, but so is morale. We need to build trust between first responders and the community—rooted in respect and communication.

What will you do to address the critical shortages of emergency personnel and lifesaving equipment within the fire department, as recently expressed by the Annapolis Professional Firefighters union?
I support ensuring the Fire Department is staffed and equipped to meet NFPA 1710 standards. That means looking closely at the budget to identify where funds can be reallocated and determining whether proper staffing can reduce costly Vision and Priorities

What is your long-term vision for Annapolis, and how will you address its main challenges and opportunities, particularly regarding City Dock redevelopment?
My long-term vision for Annapolis is to preserve the charm, history, and waterfront character that make our city so special while ensuring it remains a safe, thriving, and financially responsible place to live, work, and visit. The City Dock redevelopment is an opportunity to protect our waterfront from flooding and improve public spaces, but it must be done carefully—with fiscal discipline, respect for small businesses, and a focus on maintaining our historic identity as a boating and maritime community.

What are the most important issues facing Annapolis residents, and how will you prioritize them?
Public safety, fiscal responsibility, infrastructure, and maintaining the city’s character are my top priorities. We must ensure our police and fire departments are fully staffed and equipped, that taxpayer money is spent wisely, and that development enhances—not erodes—our small-town charm.

If elected/re-elected, what would you aim to achieve in your first six months on the council?
In my first six months, I’ll focus on building strong relationships with the Mayor, Council, and department heads, while meeting with residents and business owners in Ward 5 to understand their priorities. I’ll also review the city’s budget closely to identify areas where spending can be better managed or redirected toward public safety and essential services.

How will you improve the quality of life for residents and their families?
By ensuring safe neighborhoods, well-maintained parks, responsible growth, and efficient city services. Families should feel secure and proud to call Annapolis home. I’ll advocate for balanced budgeting that supports core services while protecting taxpayers.

How will you prioritize improving the quality of life for marginalized communities?
Every resident deserves to feel valued and heard. I’ll work to ensure city resources are allocated fairly, focusing on safety, education, and access to opportunities for all neighborhoods. A strong, united community benefits everyone.

What action will you take to address concerns related to reparative justice and creating an Office of Freedmen Affairs?
I believe history should be remembered and respected, and that all communities deserve equal access to opportunity. I’d want to fully understand the fiscal impact and purpose of any new office before supporting it. My focus will remain on fairness, equal treatment, and using taxpayer dollars responsibly.


Local Issues and Policy

What are your solutions for housing affordability, including homeownership, rental costs, and workforce housing?
We need to encourage responsible development that fits within our infrastructure, supports workforce housing, and protects existing neighborhoods. As a Realtor, I understand the importance of balancing supply and demand. Streamlining permitting, encouraging mixed-use projects, and maintaining reasonable taxes can all help make housing more attainable.


Transportation and Parking

Given traffic congestion and limited parking, how will you improve public transportation and address downtown parking issues?
We need common-sense solutions—such as better use of existing parking garages, improved signage, and stronger partnerships with private parking providers. I support exploring shuttle systems and better transit links from outer lots to downtown, especially during peak tourism seasons. The goal is to keep traffic moving while making downtown accessible for residents, workers, and visitors.


Public Safety

What is your philosophy on public safety, and how will you address growing crime and concerns with police transparency and accountability, while also promoting community well-being?
Public safety must be our top priority. That starts with supporting our police officers and firefighters through competitive pay, proper training, and strong leadership. Transparency and accountability are essential, but so is morale. We need to build trust between first responders and the community—rooted in respect and communication.

What will you do to address the critical shortages of emergency personnel and lifesaving equipment within the fire department, as recently expressed by the Annapolis Professional Firefighters union?
I support ensuring the Fire Department is staffed and equipped to meet NFPA 1710 standards. That means looking closely at the budget to identify where funds can be reallocated and determining whether proper staffing can reduce costly overtime. I have full confidence in Chief Remaley’s leadership and believe promoting from within helps maintain a strong culture of professionalism and pride.


Environment and Resiliency

As a coastal city prone to flooding, what are your plans for environmental protection, climate change resiliency, and stormwater management?
We need practical, science-based solutions to manage flooding and protect our waterfront. That means maintaining storm drains, investing in infrastructure upgrades, and ensuring redevelopment projects include strong flood mitigation measures. Protecting our environment goes hand-in-hand with protecting property values and public safety.


Economic Health and Small Business

What strategies do you propose to help Annapolis businesses thrive, especially small businesses?
As a small business owner myself, I know the challenges local entrepreneurs face. The city should streamline permits, reduce unnecessary regulations, and make it easier for businesses to operate. We should also promote tourism and local events that drive foot traffic while maintaining the character that makes Annapolis a destination.


Collaboration and Governance

How will you handle controversial issues, especially if the council is divided?
I believe in respectful debate and fact-based decision-making. I’ll listen to all sides, seek common ground, and make decisions that serve the city’s long-term best interests—not short-term politics.

What is your approach to collaborating with other council members, and state and county agencies, to achieve city goals?
Collaboration is key. I’ll maintain open communication and look for partnerships that benefit our residents—especially in areas like transportation, education, and public safety. Effective government depends on teamwork and shared goals.

How will you balance the needs of your ward's residents with the city's overall interests?
Ward 5 will always be my first responsibility, but what’s best for the ward often aligns with what’s best for the city. I’ll advocate strongly for my constituents while keeping an eye on the broader health and sustainability of Annapolis.

How will you manage public criticism as a City Council member?
By listening respectfully, staying transparent, and focusing on facts. Constructive criticism is part of leadership. I’ll stay grounded in my values and decisions I can defend with integrity.


Experience and Community Engagement

Describe your plan to work with and engage community stakeholders (residents, businesses, non-profits).
I’ll continue building relationships with local organizations, businesses, and civic groups. My involvement in the Annapolis Optimist Club has shown me the value of community partnerships. Listening, showing up, and being accessible will guide how I lead.

How will you engage with and gather feedback from residents, particularly those who feel disconnected from the city council and various departments across the city government?
Communication is key. I’ll hold regular town hall meetings, maintain an active online presence, and make myself available to residents. People should feel their voices matter—and that their elected officials are listening.

How do you plan to manage the significant time commitment of City Council duties alongside other obligations?
I’ve built my business on organization, discipline, and time management. I’ll dedicate the time necessary to serve effectively and responsibly represent Ward 5.

What values will guide your decisions as a council member?
Integrity, accountability, fiscal responsibility, and community. I believe in protecting public safety, supporting small businesses, respecting taxpayer dollars, and preserving the historic, small-town character that makes Annapolis the place we all love to call home.

Mr Papaleonti will compete with Brooks Schandelmeierr in the upcoming general election on Tuesday, November 4, 2025. All candidates who prevail in the general election will be sworn into office on Monday, December 1, 2025.  

Related: Annapolis City Council Aldermanic Candidate Profile: Brooks Schandelmeier, Ward 5

Disclaimer: This communication is shared voluntarily for informational purposes under Maryland’s press exemption and was not authorized, approved, coordinated, or paid for by any candidate, campaign, or political group. Report Annapolis News does not act or communicate on behalf of any candidate or campaign.

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