Last weekend, just two weeks before the April 1 aldermanic runoff, Mayor Daley’s troops returned to the First Ward to plead with voters to reelect the incumbent, Alderman Jesse Granato. Beefy guys have brought out votes for Granato in three closely contested elections in the last eight years, but this time, says Granato’s latest opponent, Manny Flores, the strategy will backfire.

“With all due respect to Mayor Daley–and I’m not running against him–I think this ward is ready for a little more political independence,” says Flores, a lawyer in the Cook County state’s attorney’s office. “People are tired of the same old tactics. Bringing in all these workers reflects a misunderstanding of the ward.”

It’s easy to see why someone might misunderstand the First Ward, whose boundaries have changed radically twice in the last decade. Traditionally the First Ward’s base was the predominantly Italian precincts around Taylor Street on the near south side. But in the early 1990s Mayor Daley decided to create more majority Hispanic wards to satisfy the demands of his Mexican-American allies for more seats in the City Council. So he grafted the old Taylor Street neighborhoods onto Alderman Burt Natarus’s 42nd Ward, which had been concentrated around the Gold Coast. And he took chunks of Wicker Park, Bucktown, West Town, Ukrainian Village, and East Village and stuck them on the First Ward.

Most of these chunks came from the 32nd Ward, then overseen by Alderman Terry Gabinski and Congressman Dan Rostenkowski. To win their support for the new map, Daley assured his long-standing allies that he would endorse whomever they slated to run. The mayor had only one stipulation–the candidate had to be Hispanic.

Gabinski and Rostenkowski selected Granato, an obvious choice. For one thing, he’s from the area. “I was raised in a three-flat on Hoyne and Armitage,” he says. “I graduated from Saint Ben’s High School.” Granato’s also a machine loyalist and openly admits he owes everything he’s achieved to the 32nd Ward regular organization. “I wasn’t really into politics as a kid or a teenager–I was into sports,” he says. “But as a young man I saw what the regular organization can do for a community–all the good things. I wanted to join.”

In 1979, at the age of 20, Granato became a volunteer precinct captain for Gabinski. In 1980 Gabinski rewarded him by getting him a job with the Park District. A few months later, Granato says, he was promoted to a “shirt-and-tie job” with the Cook County recorder of deeds. Later that year he got his “dream job”–office aide to Rostenkowski, then chairman of the U.S. House Ways and Means committee and one of the most powerful Democrats in Congress.

“I was 22 years old, working for the chairman of Ways and Means, which was very exciting to a young guy,” says Granato. “I was very proud of that job, and I still am. I worked for Congressman Rostenkowski from behind the counter of his service office on Damen for seven years.”

In 1988 Gabinski hired Granato to be chief of staff for his aldermanic office. “I worked with every block in the ward–I know all the community groups,” says Granato. “When you’re an aide to an alderman you do it all.”

It was Granato’s misfortune to be slated to run for alderman just when the ward was starting to rebel against machine politics. Many of the residents who’d moved to Wicker Park, Bucktown, and West Town in the early 1990s were well-educated liberals who’d supported Mayor Harold Washington–someone both Rostenkowski and Gabinski had vociferously opposed. In 1995, the first time Granato ran, most of these voters voted for Victoria Almeida. Granato only narrowly defeated her.

Four years later he won an even closer election, this time against Cynthia Soto (who has since been elected state representative). That election is the subject of a recent book self-published by Peter Zelchenko, It Happened Four Years Ago: Mayor Daley’s Brutal Conquest of Chicago’s First Ward. According to him, the mayor wanted a lackey running the First Ward, someone who wouldn’t offer strong opposition to development plans for the area. Zelchenko accuses Daley’s machine workers of using time-tested tactics to make sure Granato beat Soto–turning out absentee voters, harassing residents who supported Soto, working on the sidewalks in front of polling places in two precincts where Soto was running strong to make it difficult for voters to get inside.

“I know these guys, I know their mentality,” says Zelchenko, a former volunteer for Soto who’s now volunteering for Flores. “I grew up in Chicago. I’ve been working in independent campaigns since I was a kid. They’re school-yard bullies. They like to knock you around.”

Despite all the help, Granato beat Soto by only a few hundred votes. In the aftermath he decided to change the ward’s boundaries again. In the 2001 ward-map reapportionment, he cut loose precincts east of Spaulding and other precincts west of Ashland–two large chunks that together covered about 11 blocks. To compensate, he stretched the ward’s northern boundary from North Avenue to Belmont. Now the ward resembles an inverted question mark as it winds in and out of the 26th and 32nd wards, so that no single neighborhood–Wicker Park, Bucktown, or East Village–is wholly included.

The new boundaries make it hard for a challenger to win, because there’s no base from which to launch an insurgency campaign. “The communities are all sliced up,” says Frank Avila, a Flores supporter. “A lot of people are voting in the First Ward for the first time.”

From the start of this campaign Granato’s plan was simple. He linked his name to Daley’s, hoping the mayor’s popularity would carry him to victory. The problem with this strategy is that the mayor’s policies aren’t universally popular in the area.

According to Flores, the hot issue in the ward is development. Over the last ten years block after block has been jammed with big condo buildings. Most of this new construction required zoning changes that were passed over the objections of community groups. Residents have been howling about the consequences of the overdevelopment: traffic jams, soaring property taxes, and even more gentrification.

“There has been no master plan for development around here,” says Jonathan Fine, a founder of Preservation Chicago, a not-for-profit group that doesn’t endorse political candidates. “The new development has altered the scale of the neighborhood as two- and three-story buildings become four- and five-story buildings.”

Granato approved many of these zoning changes, though recently he’s been trying to portray himself as a preservationist, going out of his way, for instance, to try to stop the demolition of the Huntley house, one of the oldest in the city. It was torn down last year.

Going into this election, Granato was confident. He didn’t think Flores, a 31-year-old lawyer making his first run for office, was much of a challenger. He sneered that Flores was an outsider–a suburban kid raised in Du Page County who didn’t understand the ward.

But Flores kept outfoxing Granato. He hooked up with Avila, an election-law expert who beat back Granato’s attempt to knock Flores off the ballot in January. To work the precincts, Flores recruited many of the independent activists who’d helped Soto.

On February 25 Flores won more votes than Granato–3,386 to 3,330–though he fell short of the 50-percent-plus-one-vote tally needed to win outright (a third candidate received 214 votes). The result is the April 1 runoff.

In the current campaign Flores is trying to build his image as a self-made professional. “I come from humble working-class roots,” he says. “I can relate to all kinds of people. I worked hard to get where I am. A big part of my success comes from athletics. I wrestled in high school. I was also an all-conference football player, a defensive back.” He’s also stressing that he owes no allegiance to any organization.

At the start of the runoff campaign it seemed that Flores would gain from the political machinations in the 12th Ward. The incumbent there, Ray Frias, had managed to force George Cardenas into a runoff, even though Cardenas was supported by the Hispanic Democratic Organization, one of Mayor Daley’s chief precinct operations. “I think most of HDO will be busy in the 12th,” Flores predicted after February 25.

But on March 12 Frias dropped out of the race, conceding the election to Cardenas, and HDO precinct workers were free to go north to the First Ward to work for Granato.”The hordes of hell are coming–we’re the last ward, the last chance for Hispanic independence,” says Avila. “It’s Manny against the machine.”

Granato says he’s proud to have HDO’s backing. “If they’re for me, then the mayor’s for me,” he says. “I must be doing something right if Mayor Daley supports me.”

But Zelchenko says, “The ward’s changed even from four years ago–in some ways Mayor Daley’s being hoisted on his own petard. One of the results of the mayor’s strategy of jamming so much new development in this community is that the neighborhood’s changed. When you concentrate so many college-educated, privileged people in one place you can’t treat them the way you would working-class folks. You can’t use the same old tactics. Since Frias dropped, HDO brought in their guys. You should see them, going after every yuppie in an SUV. But I don’t think those school-yard-bully tactics will work. It’s a new ward.”