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Mayoral election in Annapolis, Maryland (2025)
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Local ballot measures • Municipal • How to run for office |
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← 2021
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| 2025 Annapolis elections |
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| Election dates |
| Filing deadline: July 28, 2025 & October 29, 2025 (write-in) |
| Primary election: September 16, 2025 General election: November 4, 2025 |
| Election stats |
| Offices up: Mayor |
| Total seats up: 1 (click here for other city elections) |
| Other municipal elections |
| U.S. municipal elections, 2025 |
The city of Annapolis, Maryland, is holding a general election for mayor on November 4, 2025. A primary was scheduled for September 16, 2025. The regular candidate filing deadline for this election was July 28, 2025, and the write-in candidate filing deadline is October 29, 2025.
As of 2025, Annapolis has term limits for the position of mayor. Mayors can serve two consecutive four-year terms and can run again after a four year break.
Ballotpedia comprehensively covers the 100 largest cities in the United States by population. Our coverage also includes mayors, city councils, and district attorneys in the 32 state capitals that are not already part of our largest cities coverage. Please note that there may be more offices on the ballot in this capital city than what is listed on this page.
Elections
Click on the tabs below to show more information about those topics.
Candidates and results
General election
General election for Mayor of Annapolis
Jared Littmann and Bob O'Shea are running in the general election for Mayor of Annapolis on November 4, 2025.
Candidate | ||
 | Jared Littmann (D)  | |
 | Bob O'Shea (R) | |
| ||||
| = candidate completed the Ballotpedia Candidate Connection survey. | ||||
| If you are a candidate and would like to tell readers and voters more about why they should vote for you, complete the Ballotpedia Candidate Connection Survey. | ||||
Do you want a spreadsheet of this type of data? Contact our sales team. | ||||
Democratic primary election
Democratic primary for Mayor of Annapolis
Jared Littmann defeated Rhonda Pindell Charles in the Democratic primary for Mayor of Annapolis on September 16, 2025.
Candidate | % | Votes | ||
| ✔ | | Jared Littmann | 67.1 | 2,594 |
 | Rhonda Pindell Charles | 32.9 | 1,271 | |
| Total votes: 3,865 | |||
| = candidate completed the Ballotpedia Candidate Connection survey. | ||||
| If you are a candidate and would like to tell readers and voters more about why they should vote for you, complete the Ballotpedia Candidate Connection Survey. | ||||
Do you want a spreadsheet of this type of data? Contact our sales team. | ||||
Republican primary election
The Republican primary election was canceled. Bob O'Shea advanced from the Republican primary for Mayor of Annapolis.
Additional elections on the ballot
- See also: Maryland elections, 2025
September 16, 2025
November 4, 2025
Ballotpedia's Candidate Connection survey responses
Ballotpedia asks all federal, state, and local candidates to complete a survey and share what motivates them on political and personal levels. The section below shows responses from candidates in this race who completed Ballotpedia's Candidate Connection survey. Candidates are asked three required questions for this survey, but they may answer additional optional questions as well.
Survey responses from candidates in this race
Click on a candidate's name to visit their Ballotpedia page.
Note: Ballotpedia reserves the right to edit Candidate Connection survey responses. Any edits made by Ballotpedia will be clearly marked with [brackets] for the public. If the candidate disagrees with an edit, he or she may request the full removal of the survey response from Ballotpedia.org. Ballotpedia does not edit or correct typographical errors unless the candidate's campaign requests it.
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Jared Littmann (D)
Second, I’m prepared to lead a budget process that’s thoughtful, transparent, and disciplined. I’ve managed budgets in the private sector for over 20 years as a small business owner here in Annapolis. I’ve had to make tough calls, deciding how to stretch limited resources without compromising service or quality. That’s experience I’ll bring to City Hall. I’ve also done this work as a City Council member, making difficult but necessary cuts and helping fund key priorities. I've been involved in large, complex financial transactions, including a $700 million sale to a private equity firm. And like many of you, I manage a family budget. I understand the value of a dollar, the stress of rising costs, and the importance of planning ahead.
Third, I have a plan for public safety that focuses on prevention, accountability, and smart investment. We can make Annapolis safer by filling open positions on our police force and hiring more civilian staff, equipping officers with modern tools and technology, investing in violence prevention programs, offering mentoring and recreation programs to at-risk youth, improving our mental health response, supporting reentry programs for returning citizens to reduce recidivism, and conducting an independent, professional audit of the Annapolis Police Department. I’ll lead with urgency, collaboration, and a commitment to making every neighborhood in Annapolis feel safe.
Bob O'Shea (R)
ANNAPOLIS Preservation:
Our city has a unique feel that makes Annapolis the place it is. That is why we are attracted to the area and tourists come to visit. Current City Administration and Officials are trying to make Annapolis another cookie cutter, overdeveloped destination that I vocally oppose. I support controlled development with a vision that makes Annapolis the Community that it is. I oppose the Spot Zoning Height Restrictions Relief that some past Zoning Individuals say IS NOT Spot Zoning.
CRIME / Safety:
Jared Littmann (D)
Bob O'Shea (R)
Annapolis Preservation (Enforce) Crime (Reduce and Promote Abiding to our Laws) Costs of Living (Stabilize, Lower) Overstaffed City Hall (Reduce, Create Efficiencies)
Planning, Zoning, Regulations (Empower Associates)
Bob O'Shea (R)
Bob O'Shea (R)
Jared Littmann (D)
As a business owner for 20 years, I’ve been battle-tested having managed my store through the Great Recession and the Pandemic. I’ve managed budgets, led a team, and navigated challenges that required flexibility, planning, and accountability. I’ll bring that same approach to city government, especially now, when we may be heading into a period of reduced federal funding. The next mayor will need to pivot, rethink priorities, and make sure we’re focused on essential services and delivering what matters most: public safety, infrastructure, housing, and responsive government.
Professionally, I’ve worked on complex financial and legal matters, from a $700 million private equity transaction to a $20 million government contract. I’m ready to manage big issues like the city’s budget, the future of City Dock, and one of the largest lawsuits the city has ever faced.
I will take a customer service approach to city government. When someone walks into my store, we try to make them feel like they’re important, like they’re our guest. After all, they sign our paychecks. Because of our customer service, my store has been fortunate to win awards from the community, industry groups, and the Chamber of Commerce. I want to bring that culture to city government. As a constituent, when you’re interacting with your city government, you should feel that the city cares about you and that they’re trying to figure out a way to get to yes.
I will lead with competence, urgency, and integrity, and I’ll make sure that every dollar and decision reflects what matters most to our residents. I’m ready to do the work.
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Jared Littmann (D)
The second is the flooding at City Dock. We must build as quickly as possible the infrastructure needed to protect downtown businesses and residents from the devastation of flooding, which is happening more frequently than ever before. A key to this project is securing funding, which is an absolute priority for me. I will work diligently to acquire as much funding from outside city government as possible and complete the project. Building something this complicated and expensive will require regular adjustments and attention to detail. I will bring my expertise as an engineer, lawyer, and business executive to effectively collaborate with all stakeholders and segments of government.
The third is the high cost of living in Annapolis. This issue requires a targeted, thoughtful approach, one that improves affordability without overwhelming our roads, schools, or city services. We need to increase the housing stock by fixing our permitting process and pursuing projects like the Choice Neighborhoods Initiative (CNI). This $400 million plan to redevelop Eastport Terrace and Harbour House, and expand housing at the Spa Road site, would double the number of units to 700, with mixed-use, mixed-income housing. It has the potential to transform lives and neighborhoods if done right and in collaboration with residents and neighbors.
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Bob O'Shea (R)
Jared Littmann (D)
Bob O'Shea (R)
Candidate profiles
This section includes candidate profiles that may be created in one of two ways: either the candidate completed Ballotpedia's Candidate Connection survey, or Ballotpedia staff may compile a profile based on campaign websites, advertisements, and public statements after identifying the candidate as noteworthy. For more on how we select candidates to include, click here.
Party: Democratic Party
Incumbent: No
Political Office: None
Submitted Biography: "I am proud to be running for Annapolis mayor as the Democratic nominee. I have a record of service to our community as an Alderman, a dad, and small business owner, and even as a little league coach. My wife Marlene and I run K&B Ace Hardware, a family business that has been open for over 50 years. I also co-founded another business with my wife in the liquidation hardware niche, and was hired as a corporate director of the True Value Company where I served as Board Chair. From 2013-2017, I served as Ward 5 Alderman for the City of Annapolis and have a proven track record. Before that, I worked as a lawyer for seven years, including a clerkship for Circuit Court Judge Ann Harrington and four years in the County Attorney’s Office for Montgomery County as an Associate County Attorney, where I worked on environmental and electricity law issues, civil prosecutions, and legislation and procurements. I earned my law degree from the University of Maryland in Baltimore with a focus on environmental law, and for undergrad went to Washington University in St. Louis, majoring in Engineering and Public Policy. Marlene and I have lived in Annapolis since 2010. We have two children, Isabel and Zach. I coached Isabel in soccer and then coached Zach in soccer and baseball for 10+ years. I’m running for Mayor because I want my kids, and yours, to have the same great city we did. I’ll address the challenges that the future will bring and protect the things that make Annapolis special."
Party: Republican Party
Incumbent: No
Political Office: None
Submitted Biography: "My name is Bobby O’Shea, and I am seeking your vote for the Mayor of Annapolis on the 11/2025 election. I grew up in Canandaigua, a small waterfront town in upstate New York. Canandaigua, in Seneca, means “The Chosen Spot.” I fell in love with the waterman’s way of life boating on Finger Lakes and fishing off the city pier. My mom and dad, Diana and Bob, taught me to love and respect native cultures and heritage. I am passionate about preserving history truthfully, no matter how painful it may be. In 2000, I chose Annapolis as my home because of its beauty, diverse history, and the Chesapeake Bay. My son, Trey, and I reside in Murray Hill. The ‘man’ in charge of our home is Togo, our faithful dog. Another important part of our family are the seven midshipmen we have sponsored. I was a member of the Board of Trustees for the Naval Academy Primary School. To this day I enjoy attending events at the ‘Little White Schoolhouse’ on Greenbury Point. I understand the key to success is a good education. As mayor I will work with the county and local non-profits to ensure our schools have all the resources they need, so every child thrives. I am running to be the next mayor of Annapolis because of the love and passion I have for this place we call home. Annapolis is the eight unique wards with their own distinct character and history. I want your vote so together we can make Annapolis the city she was always meant to be. This will promote Transparency, Accountability, Accessibility !"
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Mayoral partisanship
Annapolis has a Democratic mayor. As of October 2025, the mayors of 35 state capitals are affiliated with the Democratic Party, seven are Republicans, one is independent, and two are nonpartisan. The partisan affiliation of five state capital mayors is unknown. While most mayoral elections in state capital cities are nonpartisan, most officeholders are affiliated with a political party.
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About the city
- See also: Annapolis, Maryland
Annapolis is a city in Anne Arundel County, Maryland. As of 2020, its population was 40,812.
City government
- See also: Mayor-council government and Council-manager government
The city of Annapolis utilizes a council-manager system combined with a strong mayor. In this form of municipal government, the city council serves as the city's primary legislative body and the mayor serves as the city's chief executive. The mayor, however, appoints a city manager to oversee the city's day-to-day operations and execute city policies.[1]
Demographics
The following table displays demographic data provided by the United States Census Bureau.
| Demographic Data for Annapolis, Maryland | ||
|---|---|---|
| Annapolis | Maryland | |
| Population | 40,812 | 6,177,224 |
| Land area (sq mi) | 7 | 9,711 |
| Race and ethnicity** | ||
| White | 61.2% | 54.2% |
| Black/African American | 21% | 29.9% |
| Asian | 2.1% | 6.4% |
| Native American | 0.1% | 0.3% |
| Pacific Islander | 0% | 0% |
| Other (single race) | N/A | 4.7% |
| Multiple | 3.6% | 4.5% |
| Hispanic/Latino | 20.1% | 10.3% |
| Education | ||
| High school graduation rate | 88.8% | 90.6% |
| College graduation rate | 50% | 40.9% |
| Income | ||
| Median household income | $87,897 | $87,063 |
| Persons below poverty level | 10.1% | 9% |
| Source: population provided by U.S. Census Bureau, "Decennial Census" (2020). Other figures provided by U.S. Census Bureau, "American Community Survey" (5-year estimates 2015-2020). | ||
| **Note: Percentages for race and ethnicity may add up to more than 100 percent because respondents may report more than one race and the Hispanic/Latino ethnicity may be selected in conjunction with any race. Read more about race and ethnicity in the census here. | ||
See also
| Annapolis, Maryland | Maryland | Municipal government | Other local coverage |
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External links
Footnotes
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