Reverend Anthony Randall stepped to the pulpit at Twelve Gates Missionary Baptist Church, a small congregation that meets in a storefront space on West Division in Austin. "The next voice you'll hear is from someone who's become a friend of mine," he said, "and I hope he's going to become our next mayor."

Second Ward alderman Robert Fioretti was beaming as he shook the pastor's hand.

"I think of the passage from Luke: 'When he drew near and saw the city, he wept over it,'" Fioretti told the congregation. "But there is hope. We all have to work together."

Whenever he's asked, Fioretti insists that he's still weighing his options for the February municipal elections. But it sure looks like he's aiming to challenge Mayor Rahm Emanuel.

Over the last three years Fioretti has emerged as one of the few outspoken critics of Emanuel in the City Council. And the mayor has returned the love: when Emanuel's allies redrew ward boundaries two years ago, the Second Ward was so altered that Fioretti's home is no longer in it.

"I received a call, through a third party, at 10:30 the night before the remap, asking if I'd rather be in the 27th or the 28th Ward," Fioretti says. "I told them in no uncertain terms what to do with themselves."

But the deed was done, and Fioretti now lives in the new 28th. Running for alderman again would require Fioretti, who is white, to take on an incumbent in the Third, 27th, or 28th—all predominantly black wards—or move north to be within the remapped Second Ward.

"Why should I leave my home because of the mayor?" Fioretti says.

Instead he's staying in his home and preparing for a possible mayoral run. For the last four years Fioretti has been on what he calls a "listening tour": giving talks to small groups in supporters' homes, showing up at community meetings all over town, and driving side streets and alleys in every ward.

And on Sundays he goes to church—usually several of them, most in black neighborhoods where Emanuel is particularly unpopular.

Last Sunday, when I tagged along with him, Twelve Gates was his first stop.

"He knows you want change, so he's asking, how bad do you want it? Do you want to see Rahm off of the fifth floor?" —Reverend Anthony Randall, talking about Alderman Robert Fioretti

Fioretti has never been a particularly dynamic stump speaker—he's restrained and rarely gets into policy details, as if he's embarrassed about the possibility of boring the audience, or of changing his mind at some point. But he is also warm and friendly and rarely speaks for very long, all of which help his cause.

"A couple of years ago I had a bout with cancer, but I can thank the Lord now," he told the congregation.

Fioretti mentioned that he'd grown up on the south side, in the Roseland neighborhood. His childhood home was boarded up and then recently torn down, he said—a sign of the disinvestment that's hit so many neighborhoods like theirs.

"Our younger people see the shuttered schools and say, 'What are they doing to us?'"

He said more should be done to combat violence hitting neighborhoods like Austin. "We need more police, but we simply can't police our way out of these problems," he says. "Isn't it time we put our people to work? We need to invest in our people."

The congregation responded with amens. Reverend Randall nodded. "I've heard that speech about ten times so far," the pastor said. "But I know one who means it—and that's Fioretti here. He knows you want change, so he's asking, how bad do you want it? Do you want to see Rahm off of the fifth floor? Because I'd like to see him on skid row!"

Back in the car, Fioretti chuckled about the pastor's comment. "Skid row—that's pretty strong. But we need to do something different."

He threw out some ideas: creating tax-free zones to lure more businesses and jobs to struggling areas like Austin; taxing suburban commuters to Chicago and financial transactions at the Board of Trade instead of raising property taxes; ensuring that public funds are used for investing in schools and rebuilding neighborhood infrastructure "block by block."

Many of Fioretti's policy ideas are broad and not particularly original. But that doesn't mean he fails to pay attention to the small stuff. As we drove down Division and then Cicero, he offered a running list of the signs of neglect: illegal signs advertising cheap mortgages and night clubs, litter in vacant lots, trees that are diseased and need to be replaced.

"Dying, dying, dying, dying, dying, dying," he said as he pointed to the trees. "That's five or six in a row. What's it going to look like out here when they all go? Look at that beautiful building sitting there boarded up—why can't we fix these up and put people to work? Look at the gym shoes on the power line—that's a gang sign."

Fioretti grabbed his iPhone to send a message to Streets and Sanitation. "If you clean up the community, people respect it. We're doing a street light survey in our ward right now. You need to make sure all your street lights are working. All that can build pride in our city."

Fioretti is well aware that a huge number of voters are down on Emanuel and what they see as his disinterest in their neighborhoods and schools. But it's another matter to convince them to take a chance on an alderman who isn't a household name across the city.

"There are so many people who don't like him—people who normally wouldn't have anything else in common. He's been an equal opportunity offender." —Veteran political strategist Delmarie Cobb, referring to the mayor

Chicago mayors don't come out of the City Council—the last one who did was Eugene Sawyer, in 1987. And that was only after Harold Washington died in office and aldermen had to pick one of their own to serve until a special election could be held in 1989. Sawyer lost that race to Richard M. Daley, who was Cook County state's attorney.

After spending years focused on micro-level issues like parking regulations, weedy lots, and empty storefronts, most aldermen have been simply unable to build the record or name recognition needed for citywide or countywide office.

Former city clerk Miguel del Valle, who lost to Emanuel in the 2011 mayoral race, says any serious challenger would need to be well-known and start with a strong base of supporters. "Whatever they have to do to win, they had to do it years ago," he says. "Fioretti, as nice a guy as he is, he doesn't have enough of that history."

Still, del Valle notes that Emanuel is so unpopular that there could be an opportunity. A Tribune poll last week found that the mayor's approval rating has fallen to 35 percent. And while Chicago Teachers Union president Karen Lewis is the leading potential challenger, Fioretti "has gained surprising traction," the Trib reported: he had the support of 25 percent of voters in a head-to-head matchup with Emanuel even though they didn't know much about him, "a sign that there's a sizable contingent of anyone-but-Emanuel voters."

That's why veteran political strategist Delmarie Cobb believes the mayor can be defeated, especially if both Lewis and Fioretti take him on. She notes that former mayor Richard Daley never had to run for reelection against a white opponent. "It gave the impression that it was all about race, and it wasn't. If Fioretti runs, it takes that racial issue out of the campaign. It keeps Rahm from being able to duck debates. It makes the media have to cover it as a real campaign."

"He's going to try to ruin me." —Alderman Robert Fioretti, on how he expects Mayor Rahm Emanuel to react if Fioretti challenges him

Cobb says the key for any Emanuel foe is to mobilize black voters while also offering clear alternatives on issues—like the mayor's handling of the schools—that extend beyond the south and west sides. "There are so many people who don't like him—people who normally wouldn't have anything else in common," she says. "He's been an equal opportunity offender."

Fioretti says he hasn't decided whether to go for it. "We're looking forward, we're putting the team together, and we're seeing what we need to do. Rahm's base will vote—that 30 percent out there—and of course there are dollars and cents."

Which is to say that he needs to raise at least $3 million. His campaign fund had about $336,000 as of the end of June, according to state records. Emanuel's had $8.3 million.

And there's at least one other factor to consider. "He's going to try to ruin me," Fioretti said. "But as I said to one of your friends the other day, my life is an open book."

Fioretti is referring to a story in the Sun-Times last week about how two staffers for his 2007 campaign for alderman had to appeal to the state Department of Labor to get paid for their work. (The Reader and the Sun-Times share an owner.)

"I've made some mistakes and trusted some people to do some things, but that happens," he said.

And so Fioretti's listening tour continues. At Second Presbyterian in the South Loop, Fioretti addressed congregants as they held a picnic in the parking lot. "We're all going to move forward in this city together, and our churches and schools are the foundation," he said.

He then offered fist bumps to church members waiting in line for food. One thanked him for helping her with snow removal last winter. Another asked him to stand with her for a picture. "You're everywhere!" she said. Fioretti gave her a hug.

Then he was off to another church.