Whatever the outcome, the next alderman for Ward 5 will be a political newcomer.
A week from today, voters will have their choice between Democrat Mathew Silverman, a county police officer, and Republican James Conley, who works in finance.
Both candidates said they are more similar than different on the issues. What the election will come down to is the different skills they can bring to the council, they said.
At stake is the seat currently held by two-term Republican Alderman David Cordle, who is leaving the seat in hopes of becoming the next mayor.
The ward, which lies largely along the city's southern boundary, is mostly a series of residential neighborhoods. There are few businesses and a few churches. It includes Hunt Meadow, the area north of Annapolis Middle School and Harness Creek View.
While they are admittedly similar on most topics, the candidates disagree on the need for a tax cap that would limit how much revenue city government could collect each year.
"You're limiting what's going to happen in the future," Silverman said. "Nobody knows what the future holds."
Additionally, there are hidden expenses. For example, if there is a tax cap, civil-servant salaries aren't going to be as competitive in Annapolis as other jurisdictions. City employees will take jobs elsewhere and Annapolis government will be stuck covering the expenses to train replacements, Silverman said.
But Conley disagreed.
"I'm 100 percent for the tax cap," he said.
He pointed to the county as an example of where the tax cap has worked. Services have been cut - as have expenses - but he said he doesn't believe it would hinder the city.
He said he wants the city to apply for more federal grants to cover expenses, allowing the city to maintain some of its spending without having to collect more revenue, Conley said.
Both candidates said overcrowded homes are a big issue in their ward. In some cases, there will be as many as five families living under a single roof and many times these residents are illegal immigrants, they said.
"There's square-footage issues," Conley said. "There's permit issues. There's too many cars. A, it's not a safe environment. And B, it's overcrowding."
Silverman, 30, said that this type of living situation involving illegal immigrants perpetuated crimes. Just like residents all over the city, illegal immigrants are robbed and attacked. But because of their immigration status, they are afraid to tell police they were a victim of a crime. Meanwhile, the person who robbed them uses their ill-gotten money to buy drugs and guns that they bring back to Annapolis, Silverman said.
Conley's financial history has come into question during the campaign. His former home is in foreclosure and he has twice filed for bankruptcy. In the most recent round he owed 32 investors $1.175 million for a mortgage on his home, a Lexus, a time share and other assets. Foreclosure proceedings began on his old home in 2008.
Also, Conley, 46, is being sued for allegedly misleading someone into investing into a diamond mine in Ghana in West Africa.
He said his financial troubles are over and were "a snapshot of a period of my life. It's not a portrait of my life."
He has since been given the authority to approve $750 million bonds for his work and has passed criminal background checks that allow him to work with children as a volunteer, Conley said.
He said his bankruptcy proceedings ended Sept. 15 and the diamond-mine lawsuit against him was dropped. However, court records show the diamond-mine case is still active. Conley said he would provide The Capital with copies of his own legal records showing the lawsuit was over, but he has not yet made them available.
A lawyer for the plaintiff said the case against Conley is still standing, but it could not move through the court system because of the bankruptcy proceedings.
Of the ward's registered voters, 1,150 are Democrats, 817 are Republicans and 478 are unaffiliated. While there is a heavy Democratic presence, the ward has been represented by Republicans since 1997.
The last Democrat to hold the City Council seat was civil-rights activist Carl Snowden, who left the post in an unsuccessful bid for mayor. Voters replaced him with Republican Herb McMillan, the current president of the Maryland Taxpayers Association.
The most recent round of campaign finance reports show Silverman has more money to spend in the final stretch to the general election with $746 on hand; Conley has $335. Also, in the last reporting period Silverman spent more money, $423 to Conley's $335.
Editor's note: This is one in a series of previews of contested races for the Annapolis City Council prior to the Nov. 3 election.
Tomorrow: The Ward 6 race.
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