Like many Baltimoreans who have fallen on hard times, they want something from their politicians. And this crowd doesn't shy away from asking.
One woman asked for legal advice. Another rolled up her sleeves to display what appeared to be dozens of bug bites and told Conaway her landlord is a deadbeat. And a man asked in a low whisper if Conaway could spare 50 cents.
"My thing is jobs, jobs, jobs," said Conaway, 78, who oversees a staff of about 250 and a budget of $10 million as clerk of the Balltimore Circuit Court and now is making his fourth run for mayor.
"If you get jobs, that will cure a lot of ills that we have. People who don't have jobs turn to crime because they don't have anything to do."
Conaway, who served two terms in the House of Delegates in the 1970s and 1980s, has earned attention over the years with campaign stunts. He has identified himself in campaign literature as the "Papa Bear" of "The Four Bears"— Conaway; his wife, Mary, the city's register of wills; daughter Belinda, a City Council member; and son Frank Jr., a member of the House of Delegates — and encouraged supporters to dress in furry bear costumes.
He debuted a rap song last month dissing his primary opponents; while he didn't rap on the track, he says he helped write the lyrics. And he has handed out brooms emblazoned with his name.
"We need to clean up the city," he said. "And we need to sweep some people out of office."
Conway's approach to creating jobs is wide-ranging.
He has proposed widening a downtown rail tunnel to more effectively accommodate freight trains, a move that he says would bring the city 15,000 jobs. As mayor, he would serve as a "goodwill ambassador, a salesperson" for the city. He says he would offer tax credits to entrepreneurs who open small businesses in the city. When pressed for details, he said he would "cut taxes in half."
"We gotta have a mayor that promotes jobs," he said.