"I never take anything for granted," City Councillor Michael A. Sullivan said earlier this summer. "Election Day is 365 days a year for me. There are a number of people who can challenge for a spot. Anyone who works at it has a legitimate chance."
He added that education will be his key issue.
According to Winters, demographic shifts could also influence the election's outcome, since the end of rent control has changed the profile of the typical Cambridge voter.
"The city has a better education level and a higher income. [And] you have to appeal to the person who was born and raised in Cambridge," Winters said. "People don't have a sense of what their political base is."
Two candidates, at least, appear to be targeting non-traditional voters: MIT senior Erik Snowberg, who wants the support of student voters, and Cantabrigian James Braude.
"People feel that they have very little ability to affect the outcomes," said Braude, explaining the decline in voter participation. To draw in voters, Braude is advocating an office of constituent services.
Perhaps the way to win is to offer voter-friendly services, according to Winters.
"The Cambridge City Council doesn't vote on the death penalty, and their opinions on abortion are of little consequence," he said. "Who people will choose comes down to smaller items that make the city tick."