Mayor Rahm Emanuel and Cook County board president Toni Preckwinkle, the two most powerful politicians in Chicago-area government, rarely appear together in public. In fact, they almost never even mention each other. Neither will admit to a rivalry, but during the primary election season two years ago they endorsed opposing candidates in local and statewide races, and Preckwinkle is widely viewed as one of Emanuel’s potential challengers in the 2015 mayoral election.

But on February 18 they held a joint press conference to endorse a little-known candidate for an open seat on the county board.

The event wasn’t carefully choreographed. It was held downtown at the Union League Club, far from the area represented by the seat: the struggling west-side neighborhoods and adjacent suburbs of the First District. And it started more than 20 minutes late. Once the officials finally appeared, the mayor fidgeted as he waited for his turn to praise 27-year-old attorney Blake Sercye.

Yet it was quickly evident why Emanuel and Preckwinkle were both weighing in on a race with little obvious interest across the city and county. They wanted to be seen standing up against the very real prospect of a convicted felon being elected to local office—and filling a power vacuum in a troubled part of Chicago.

Even before Sercye had a chance to speak, Preckwinkle ripped into the candidacy of former alderman Isaac Carothers, who’s running in the March 18 primary after serving federal time for bribery and tax evasion. “I believe those convicted of crimes can have second acts in life,” Preckwinkle said. “I also believe that abusing the public trust, taking bribes, and abusing tax dollars should disqualify you from holding elected office.”

They wouldn’t have called the press conference if they thought Carothers had no shot of winning.

The west side faces a staggering set of challenges, starting with generations of disinvestment, rampant poverty, and open-air drug markets that serve as one of the area’s largest employers. It’s also been known for rough-and-tumble politics for decades.

Through the racial changes of the 1960s and ’70s, the west side was controlled by white ward bosses, some of whom lived in other parts of the city—a setup known as “plantation politics.” Many of their African-American successors held on to office by continuing to report to more powerful politicians downtown. Most wards are still dominated by a single long-standing figure or family, and independent candidates are typically crushed or co-opted.

Carothers grew up in one of the area’s best-known political families. His grandfather was a state legislator and one of the first African-American ward committeemen on the west side. His father served as both committeeman and alderman before being convicted of taking bribes in 1983.

In 1999, Carothers was elected 29th Ward alderman, defeating a candidate backed by Congressman Danny Davis, and in 2000 he ousted Davis as Democratic committeeman. For the next decade his ward organization controlled dozens of public-sector jobs and was the most potent political force on the west side.

He also had a job to do at City Hall. With a growling demeanor and the build of a lineman, he used his position as chairman of the police and fire committee to help clear the way for Mayor Richard M. Daley’s agenda.

But in 2009 the feds indicted Carothers for receiving $40,000 worth of renovations on his home from a developer who needed a zoning change for a residential project. Carothers eventually pleaded guilty to federal bribery and tax evasion charges and was sentenced to 28 months in prison.

Since being released, he’s worked at the Safer Foundation, which helps ex-offenders find jobs. He’s also been calling in chits from some of the many politicians and public-sector workers who owe him, according to other west-side pols. Though he hasn’t reported raising a dime, Carothers is expected to have a ground game heading into the election, and it’s widely believed that name recognition alone makes him the candidate to beat.

To those who suggest he sold out his community the last time around, Carothers casts himself as a flawed and repentant man—while also claiming he was overzealously prosecuted by the feds and deserves a second chance, like thousands of other ex-offenders on the west side.

Carothers concedes that it was “inappropriate” for the developer to pay for repairs to his house. But he insists that he never actually accepted a bribe, even though he pleaded guilty to doing so.

“People plead guilty for many different reasons, and not always because they feel that they’re guilty,” he says. “I can tell you that there was never any intent on my part in terms of a bribe. That never was the case, but that’s how the government framed it. There was no ‘You do this for me and I’ll do this for you.'”

He goes on to say that “no one would have ever had to bribe me to bring something that I was going to benefit from, that the whole community was going to benefit from.” Plus, “If I was in the business of trying to bribe people, get money for something, I think I would have been much more aggressive about it. This guy made six or seven million dollars, and not a dime of that came to me. He just paid for something.”

Carothers says he would try to regain his aldermanic seat again if he could, but he’s prohibited by law from running for municipal office. When commissioner Earlean Collins decided to step down after 16 outspoken but mercurial years on the county board, Carothers decided it was time to get back into politics. “This is what I do,” he says.

His best-funded and most experienced opponent is lawyer and lobbyist Richard Boykin, a former chief of staff to Congressman Davis who speaks in the measured, deep-voiced cadence of his mentor. “The era of bossism is over,” Boykin proclaims. “I want to liberate the people.”

He and Carothers have been happy to blast away at each other. Carothers doesn’t refer to Boykin by name—he calls him “Danny Davis’s guy”—but questions what he and the congressman have accomplished. “Danny has always been more philosophical, and I believed in getting down and being sure things happen,” Carothers says.

“I’ll tell you what we’ve done,” Boykin responds. “We passed a Second Chance Act so people like Ike Carothers can get out of a correctional institution and go to work for the Safer Foundation and have another chance.”

The winner of the board seat could be in a strong position to succeed Davis in Washington, and it’s no secret that Boykin has his eyes on that prize. Other politicians—on the west side and downtown—wonder why they should help him move to the front of the line.

He’s also had to respond to allegations that he doesn’t actually live in the First District, since records show he owns a home in Will County. Boykin says he’s separated from his wife, who lives there while he’s been in Oak Park for eight years.

And while he’s not an ex-con, Boykin has his own troubled past: he’s occasionally supported Republicans. Boykin donated at least $8,500 to Republican Mark Kirk, who narrowly won Barack Obama’s old U.S. Senate seat in 2010. Boykin says Kirk is an old friend from his days in Washington, but to many local Democrats that’s an unforgivable sin.

Boykin’s closing argument is that he’s not the corrupt guy. “This is a two-person race,” Boykin says. “Any vote for anybody else is a vote for Ike Carothers.”

He may be right, but it’s a risk Preckwinkle and Emanuel decided to take. Neither wants to look passive while Carothers makes a bid to regain his clout on the west side. Ruling out the Republican sympathizer they can’t control, they turned to Sercye, who’d been campaigning and raising money since last summer. Preckwinkle says she and the mayor will each add $50,000 to Sercye’s coffers.

Sercye has an impressive story—he was raised by a single mother in Austin and moved back there after attending Princeton and the University of Chicago law school. Plus, he’s already shown his political skills and loyalties. He worked as a volunteer for Emanuel’s 2011 mayoral campaign and served with both Emanuel and Preckwinkle on the state commission overseeing the west-side medical district.

“Part of the reason I’m running is to show that we have quality representation on the west side,” Sercye says. “I’m sick of the west side being a joke, and someplace no one wants to go.”

But during the highest-profile moment of his political career, the west side was barely mentioned. Instead, President Preckwinkle used the press conference to dismiss Carothers and stress that she sees Sercye as a potential “governing partner” on the county board. Emanuel said he hopes Sercye can join his fight for “reform and change.” The mayor then left the event before taking questions.

“I didn’t start the race with this support,” Sercye said at the press conference. “I’m proud to have worked hard enough to get this attention.”

He was barely finished before Preckwinkle jumped in to add her view of how Sercye would retain his independence.

“I know that people you support aren’t always going to agree with you,” Preckwinkle said. “But you try to pick the people who share your values and your concerns.”

This being Chicago, perhaps it’s not shocking that a federal bribery case is at the center of a second race on the west side. As his challengers trade shots, state rep Derrick Smith is campaigning hard to hold on to his seat despite facing a trial in May.

Smith was appointed to represent the Tenth legislative district, on the near-north and west sides, in 2011. But just before the 2012 Democratic primary, the feds indicted him for allegedly being caught on tape accepting a $7,000 bribe. Smith famously won the Democratic primary anyway. In response, his colleagues booted him out of the house. Voters turned around and reelected him that November.

Smith benefited from the shifting and contentious relationships of other west-side politicians. His original sponsor, secretary of state Jesse White, backed another candidate, but some members of White’s 27th Ward organization remained loyal to Smith. And in the western half of the district, Smith was aided by former alderman Ed Smith (no relation). Ed Smith still runs the 28th Ward organization though he’s officially retired, and he doesn’t want to let White amass any more clout.

The jockeying hasn’t stopped in the year and a half since then. White has now joined Second Ward alderman Robert Fioretti in backing Eddie Winters, an antiterrorism specialist for the Chicago Police Department, in his run against Derrick Smith. Winters promises to bring development to the district and to fight corruption. “I don’t owe anybody anything,” he says.

But Ed Smith has declared that Winters isn’t fit for the job. During at least one campaign stop at a west-side church, he called Winters a wife beater. Winters responded by suing Smith for slander.

Ed Smith isn’t keen on Derrick Smith anymore either. He’s thrown his support behind a third contender, attorney Pamela Reaves-Harris, who’s also pledging to bring jobs and a fresh perspective. “The district is in need of stability,” she says. She bristles at the notion that she’s being used as part of a west-side power struggle. “They question my motives as if I’m some sort of puppet. It’s offensive.”

While the challengers exchange blows, Representative Smith is keeping a low profile—skipping candidates’ forums and avoiding the media (including me) while spending his days knocking on doors. And he’s not doing it alone. Smith has received money and staff from house speaker Michael Madigan.

In Chicago, that’s often proved to be a winning formula.

Correction: This article has been amended to reflect that Mark Kirk won Obama’s old U.S. Senate seat in 2010.