Bob O'Shea
Bob O'Shea (Republican Party) is running for election for Mayor of Annapolis in Maryland. He is on the ballot in the general election on November 4, 2025. The Republican primary for this office on September 16, 2025, was canceled.
O'Shea completed Ballotpedia's Candidate Connection survey in 2025. Click here to read the survey answers.
Biography
Bob O'Shea was born in New Castle, Pennsylvania. He earned a high school diploma from the Canandaigua Academy. O'Shea's career experience includes working as a program manager and consultant. As of 2025, he was affiliated with the Association of Old Crows, the Association of the United States Army, and the United States Naval Institute.[1]
Elections
2025
See also: Mayoral election in Annapolis, Maryland (2025)
General election
The candidate list in this election may not be complete.
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)  | |
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| = 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. | ||||
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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.
Endorsements
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2018
General election
General election for Maryland House of Delegates District 30A (2 seats)
Incumbent Michael Busch and Alice Cain defeated Chelsea Gill and Bob O'Shea in the general election for Maryland House of Delegates District 30A on November 6, 2018.
Candidate | % | Votes | ||
| ✔ |  | Michael Busch (D) | 32.6 | 20,080 |
| ✔ |  | Alice Cain (D) | 29.3 | 18,070 |
 | Chelsea Gill (R) | 19.6 | 12,097 | |
| Bob O'Shea (R) | 18.4 | 11,324 | |
| Other/Write-in votes | 0.1 | 53 | ||
| Total votes: 61,624 | |||
| = 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 Maryland House of Delegates District 30A (2 seats)
Incumbent Michael Busch and Alice Cain defeated Aron Axe and Mary Reese in the Democratic primary for Maryland House of Delegates District 30A on June 26, 2018.
Candidate | % | Votes | ||
| ✔ | | Michael Busch | 40.2 | 5,832 |
| ✔ | | Alice Cain | 28.0 | 4,053 |
| Aron Axe | 19.1 | 2,773 | ||
| Mary Reese | 12.7 | 1,841 | ||
| Total votes: 14,499 | |||
| = 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
Republican primary for Maryland House of Delegates District 30A (2 seats)
Bob O'Shea and Chelsea Gill defeated B. Darren Burns and Doug Rathell in the Republican primary for Maryland House of Delegates District 30A on June 26, 2018.
Candidate | % | Votes | ||
| ✔ | | Bob O'Shea | 39.0 | 2,091 |
| ✔ | | Chelsea Gill | 23.6 | 1,264 |
| B. Darren Burns | 19.8 | 1,064 | ||
| Doug Rathell | 17.6 | 945 | ||
| Total votes: 5,364 | |||
| = 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. | ||||
Campaign themes
2025
Ballotpedia survey responses
See also: Ballotpedia's Candidate Connection
Bob O'Shea completed Ballotpedia's Candidate Connection survey in 2025. The survey questions appear in bold and are followed by O'Shea's responses. Candidates are asked three required questions for this survey, but they may answer additional optional questions as well.
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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 !- The budget in Annapolis has risen from 106 million in 2017 to over 200 million today. Public safety is underfunded. Our streets are lined with potholes & 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 & redundancy, not in neighborhood needs. As mayor, I will freeze non-essential administrative growth & conduct a top-to-bottom efficiency audit. Then redirect the savings to paving, parks, stormwater, & facility upkeep. Annapolis residents deserve visible, reliable results for every tax dollar. As mayor, I will cut waste and invest in maintenance, prevention. I will reduce the budget for residents who fund it.
- 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: For 2025, CrimeGrade.org gives Annapolis an Overall D- Rating, with Violent and Property Crime topping the statistics. Crime costs our city over $30 Million a year according to the report. Why are certain crime incidents NOT reported, such as Shots fired? Is this to lower the city’s actual Crime Statistics? ArcGIS reports incidents involving homicide, shootings, and shots fired are up 50% from 24 to 37 year-to-date. My administration will host regular community walks and resident listening sessions to build trust. 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.
Annapolis Preservation (Enforce)
Crime (Reduce and Promote Abiding to our Laws)
Costs of Living (Stabilize, Lower)
Overstaffed City Hall (Reduce, Create Efficiencies)
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.
See also
2025 Elections
External links
Footnotes
- ↑ Information submitted to Ballotpedia through the Candidate Connection survey on August 28, 2025
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