Robert O’Shea wants to do things differently if elected mayor of Annapolis.
The candidate, who this month played guitar in response to a question at a mayoral forum on the arts, is pitching broad changes to city financing. He says he could think outside the box to solve city and local governance issues.
“I really would like to see change,” O’Shea said in an interview. “The city has been going over and over and over again, dealing with the same things, and they seem like they don’t get resolved.”
O’Shea, who will be 66 years old on Election Day, is running against Democrat Jared Littmann, a former alderman and current hardware store owner, in the Nov. 4 city election to be the next mayor of Annapolis. The winner of the election will replace term-limited Democratic Mayor Gavin Buckley, after his second four-year term.
O’Shea is worried, he said, that the current council isn’t listening to residents concerned about overdevelopment in the city and want to slow down the process of development. At a meeting during the election cycle, O’Shea stood in front of the council for 30 seconds without talking, saying that that’s what the council should be doing: listening to constituents.
“It sounds like these people don’t listen,” O’Shea said.
The candidate grew up in the Finger Lakes area of New York and moved to the city in 2000, he said.
O’Shea is a consultant in the defense and medical industries, he said. He has worked on an antimissile system used in Israel and on COVID-19 tests, he said. He got his first job without a college degree and learned the industry firsthand.
Now the Republican nominee for mayor, he ran against Michael Pantelides and Frank Bradley in the 2013 mayoral primary. O’Shea received about 31% of the primary vote that year. Pantelides won the primary and the general election, serving for one term. O’Shea ran for the Maryland House of Delegates 30A seat in 2018 but lost to two Democrats for the two-seat position.
What made O’Shea run again this election cycle, he said, was the ignored frustration of residents over moving forward with the City Dock Resiliency Project , which is set to include flood mitigation barriers, a park and a Maritime Welcome Center. He opposes the current plans for the Maritime Welcome Center because he believes the design is not consistent with the historic district and is concerned about moving forward with pending lawsuits against the project and a still-missing $33 million grant from the Federal Emergency Management Agency. The candidate proposes a reevaluation of the project, which has been in the works for about a decade, to ensure that the flood mitigation parts are prioritized.

“When you hear all of the outpouring about how people don’t like the design, they don’t like the plan that was going on with City Dock, why would this be moving on?” O’Shea said.
His top policy priorities, O’Shea said, are improving public safety and decreasing tax and fee burdens on residents.
Throughout his campaign, O’Shea has criticized the size of the city budget. He is pushing to cut the budget by 10%, about $20 million, to save $10 million and reinvest the other $10 million into city police, fire and infrastructure.
O’Shea said he would trim the budget by sharing some city responsibilities with Anne Arundel County or eliminating some city offices and diverting those responsibilities to the county, such as the city office of parks and recreation. O’Shea said he wants to decrease the number of people working in the mayor’s office to eliminate redundancy, but did not have an answer for how many jobs he would reduce.
The candidate said he is committed to not raising taxes and “trying to” lower taxes. He supports a 2% assessment rate cap for property tax increases, to align the city with county policies.
O’Shea also wants to look into how police and fire responses will be affected by new housing developments in the city, to ensure that all residents maintain the same level or better quality of service. He also wants to ensure that the departments are fully staffed and that police have a more regular presence in city neighborhoods.
The candidate has also proposed establishing a grant office and collaborative strategy to increase the number of student resource officers in schools and fund more advanced training for the city police department to respond to dangerous situations in local public and private schools.
O’Shea also has a plan to reduce traffic congestion in the city that includes mandating traffic impact studies for developments over 10 units and installing real-time crash detection technology in high-trafficked areas.
Lisa Nichols first met O’Shea when he was running in the 2013 city election, and they have since become friends. She said what makes O’Shea stand out in the race is his ability to reach all people.
“Bob has the tenacity and the passion to run for mayor,” Nichols said. “I see Bobby’s being the type that would listen to all people, not just those on the Republican side.”
One of O’Shea’s neighbors, Richard Edwards, called O’Shea friendly and a doer of good deeds, including performing CPR on one of their neighbors.
“He’s humble and clearly a hard worker,” Edwards said. “He believes in Annapolis … and wants to see Annapolis be successful. He has the character to kind of be the figurehead for the city.”
The current Annapolis City Council is made up entirely of Democrats, and the mayor is also a Democrat. Four aldermen are not running for reelection, and every seat on the council is up to voters in November.
Littmann, who is running against O’Shea in the general election, said what distinguishes the candidates the most is experience. Littmann has had experience in city government and owning a business in the city, which he says gives him a firsthand perspective on how the city operates and problems to solve.
The current annual salary for the mayor of Annapolis $98,000. The City Council is expected to consider raising the mayoral salary to $120,000 by the end of its term. O’Shea’s campaign raised $5,610 as of Sept. 7.
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