Critics derisively referred to them as "Sheila Louise" for their like-minded views and persistent clashes with Mayor Ellen Moyer (D). Supporters called them among the best-informed aldermen on the Annapolis City Council.
Now Louise Hammond (D-Ward 1) and Sheila Tolliver (D-Ward 2) will simultaneously give up their seats in two of the city's most influential wards.
Consequently, the Nov. 8 election will allow voters to dramatically recast a council that has been shaped of late by personality conflicts and staunch alliances.
Residents across the two adjacent election districts share many of the same concerns, including rising property taxes, increasing traffic woes and crime. Residents also frown on the contentiousness that has marked City Council meetings.
Here's a breakdown of the two election races:
Ward 1: With its narrow streets and Georgian charm, the city's downtown district is home to some of Annapolis's most affluent residents -- and some of its most vocal.
"It's the most active ward in the city," said Hammond, who served its residents for 12 years. "Much of what goes on at City Hall affects [residents] more than the other wards, so they have an interest in knowing what's going on."
It's also a ward where the needs of business owners in the heart of the city's tourism center often collide with those of historic preservationists and homeowners. And the ward is home to some of the city's poorest residents in Bloomsbury Square, a public housing project along College Creek.
Serving those competing interests presents special challenges to the candidates seeking to replace Hammond: Democrat Richard E. Israel and Republican Doug Burkhardt. Both had easy runs through the primaries: Burkhardt was unchallenged; Israel won handily.
The general election stands to be more challenging. Both have run strong door-to-door campaigns. Though both are seeking office for the first time, each has a history of civic involvement.
Israel, 62, a former state assistant attorney general, said his immediate concerns for the ward include crime and parking shortages downtown, particularly for those who live there.
But Israel said his top priority is lowering the cap on the city's homestead tax credit, which limits the amount by which taxable assessments on primary residences can increase each year. Measures that would have cut the maximum increase in taxable assessments each year from 10 percent to 4 percent have twice failed to pass the City Council in the last three years. And while the council has lowered the rate at which assessments are taxed each of those years, tax bills have gone up, in large part because of soaring assessments.
"From Dock Street to Boxwood Road, that's the one thing residents tell me they want the most," said Israel, a Murray Hill resident.
But Israel calls for a cautious approach in lowering the cap so as not to hurt the city's credit rating on the bond market. The city has an AA+ rating. The Moyer administration warned earlier this year that lowering the tax cap might hurt the city's chances of gaining a higher AAA rating.
"I want the bond counsel to say what would be an acceptable limit," Israel said. "When the city issues bonds, it's pledging its taxing power. It's saying we will levy whatever taxes are necessary to ensure you get your money."
Burkhardt, 47, also a Murray Hill resident, lists tax relief third on his list of concerns, behind crime and unchecked growth, an issue that encompasses downtown's parking woes. He favors a 2 percent homestead tax credit cap -- a move he said would be a step toward "fiscal restraint and transparency in government."
"People feel slighted by this administration," he said. "They claim that they're lowering taxes, and the tax bills are going up."
Burkhardt says his top priority is putting more police foot patrols on the streets and stepping up enforcement against even lesser crimes such as vandalism and urination in public -- an approach modeled after that of former New York City mayor Rudolph Giuliani. "I believe there's a huge complacency in this city, and within the City Council, that crime is something you cannot address," he said.
Israel's campaign literature calls for greater attention to Neighborhood Watch programs, though he, too, says he would like more police foot patrols.
Both candidates say they would bring an independent yet collegial voice to a council that has been divided by infighting, though Burkhardt adds that he "is not aligned with the mayor or funded by the mayor" -- a reference to campaign finance reports that show that some of Israel's donors are also Moyer's.
Israel responds that his supporters also include many of Hammond's longtime backers.
"My opponent talks about alignments," Israel said. "I want to be an independent voice on council."
Ward 2: One of the most diverse voting districts in the city, Ward 2 includes the middle- to upper-income neighborhoods of West Annapolis and Admiral Heights, as well as the crime- and poverty-stricken Clay Street corridor, with two of the country's oldest public housing complexes.
Tolliver, who served two terms, enjoyed strong support in her ward, including from the candidates seeking to replace her.
Mike Christman, 43, a West Annapolis resident and Naval Academy alumnus, defeated two other candidates in the Republican primary. The director of a start-up software company, Christman said he wouldn't have run if Tolliver had stayed.
"I think she's done a very good job in trying to keep the administration as accountable and transparent as she could," Christman said. "And with her retirement, I felt the need to at least maintain the standards she set, if not try to improve on them."
He favors the 4 percent tax credit cap that Tolliver twice unsuccessfully introduced before the council.
Democrat Debbie Rosen McKerrow, 57, of Admiral Heights, said the number one worry about the ward's future is traffic. The ward is squeezed between two giant construction projects underway along West Street: Park Place and Westbridge Village.
"Annapolis's traffic woes grow worse every year," she said. "It's time to sit down and work toward creative solutions."
Both candidates are making a first run for political office.
McKerrow, president of an estate planning service, says her campaign is the next step in a lifetime of civic involvement. Like Christman, McKerrow is a longtime supporter of Tolliver's and has frequently testified before the council on behalf of measures introduced by the outgoing alderman. But McKerrow said she would bring a different, less confrontational style: "I'm going to really try to be pragmatic, both with the council and with the relationship with the mayor."
On the homestead tax credit, for example, McKerrow said she would seek a compromise between the 4 percent cap supported by Tolliver and the current administration's insistence that it remain at 10 percent.
"As many times as it came to council, there should have been a compromise," she said. "But people dug in. If there had been a compromise, we would have a lower rate."
McKerrow and Christman both live in the houses they grew up in and recall days of a gentler Annapolis. Reducing crime is high on their lists of priorities. Both call for a return to the notion of beat cops who walk the neighborhoods daily and know the residents by name.
McKerrow said she also wants greater attention paid to affordable housing.
Christman said the greatest crisis facing the council and the administration is regaining the trust of the citizens.
"Going out and knocking on doors the last several months, what resonates is transparency in government," he said. "Hammond said it best when she said the city of Annapolis has lost the respect of its citizens."