U.S. Rep Jesse Jackson Jr. outside Metra headquarters to protest the lack of minority hiring on the Englewood Flyover project.
U.S. Rep Jesse Jackson Jr. outside Metra headquarters to protest the lack of minority hiring on the Englewood Flyover project. Credit: Rich Hein/Sun-Times

The resignation last week of Alderman Sandi Jackson had me recalling that time, not so long ago, when her husband and political sponsor, Congressman Jesse Jackson Jr., was the great hope for progressive politics in Chicago.

This was, of course, before his escapades with the blond became a front-page embarrassment, before the federal investigation into whether he tried to buy an appointment to Barack Obama’s vacant senate seat, and before all of it led to his mental breakdown, hospitalization, virtual disappearance, and resignation.

You know, before he became the punch line to a joke about the vagaries of Chicago politics.

Instead, go back in time to 2005, when Mayor Daley—staggering through his fifth term—was mired in several major corruption scandals, including a City Hall job-rigging scam that had the feds knocking at his mayoral door.

On top of that, the trains weren’t even running on time. Worse, the two primary public transit lines—the Red and Blue—were falling apart for lack of adequate maintenance.

In rode Congressman Jackson, like a knight on a horse: handsome, charming, charismatic, quick on his feet, articulate. He looked like the total package for the 2007 mayoral election. He had strong support in the black community, thanks to his father’s civil rights legacy. And yet, unlike his father, he played well with white people. He presented himself as less like his father and more of a “postracial” black politician, like Obama.

More to the point, Junior was unafraid to do what so many other local pols wouldn’t dare: blast away at Mayor Daley.

“In our lifetime we have witnessed the impossible,” Jackson proclaimed to a cheering crowd of city workers at a rally on the northwest side in the summer of 2005. “Every single day of our lives, we are taught to believe in the impossible. And because we believe in the impossible, you’ve got to believe that in Chicago we can pay workers a living wage, that we can solve this city’s labor disputes, and that we can provide equality for all Chicagoans.”

It was obvious to everyone at that event—especially Frank Coconate, the city worker who convened it—that Jackson was gearing up to challenge Daley for mayor. “No doubt in my mind,” Coconate says.

For the better part of the next year, Jackson maintained a strong public presence, assailing corruption, bloated spending, harsh treatment of unions, and poorly conceived infrastructure planning. He feverishly worked behind the scenes to line up a rainbow dream ticket, with Alderman Rick Munoz running for treasurer and former county board commissioner Mike Quigley for city clerk.

In November of 2006—just weeks before the filing deadline—he invited my colleague Mick Dumke down to his South Shore office. Shimmering with bravado, he showed off the sophisticated campaign operation he’d put together to take on the Man.

Mick wrote: “‘Hey,’ he said, laughing so hard he bent over, ‘maybe after 17 years in office Mayor Daley will step down and run with me for city clerk!'”

Alas, a few days later he announced that he wasn’t running after all. Not because he was afraid of Daley, mind you—absolutely not. “I could beat Mayor Daley,” he declared. But with Democrats taking control of the U.S. House, he decided he wanted to use his slot on the appropriations committee to ensure that Illinois got at least its fair share of the federal funding pie.

Yeah, right. It was obvious to all that Daley had bullied him out of the race. Probably the usual way—by stroking his ego while squeezing his nuts. You know, telling him the campaign could get real dirty while suggesting that if he played ball, it might mean a crucial endorsement somewhere down the road.

In retrospect, I can understand why he folded. It would have been an uphill fight. Daley had more money and the backing of civic Chicago, which, as always, was ready to ignore all the corruption in the name of stability.

More to the point, almost all the major politicians in town, fearing the mayor, had spurned Jackson’s overtures, including nominal independents like Munoz and Quigley. If Jackson was running, he’d be running alone.

In any regard, it looked like he’d wussed out—avoiding the fight after talking it up. Which in Chicago, a city that worships toughness, may be worse than getting your butt whupped at the polls.

Jackson backed a number of candidates for alderman, most notably his wife, Sandi. But in skipping the mayoral race he lost a lot of credibility that he never regained. When the investigations and embarrassments mounted, he slid downhill fast.

Just as significant is what his departure meant for the oddball coalition of progressives, liberals, and union activists still left in this town.

It’s so hard to find serious progressive contenders—and just when they thought they had one, he bowed out. In 2007 Daley stepped around the scandals and rolled to reelection over lackluster opposition. And when Daley decided to hang it up three years later, Rahm Emanuel—backed by the Daleys—brought his emperor’s act to town.

The 2011 election basically came down to a battle between two factions of the Daley machine: Emanuel versus Gery Chico, Daley’s former chief of staff and school board president. Emanuel won largely thanks to the support of black voters, who mistakenly thought they were voting for President Obama’s guy.

Emanuel rewarded their loyalty by firing black city workers, closing schools in black communities, and doling out economic development dollars to well-connected downtown developers.

All things that Jackson presumably would have opposed.

In Jackson’s absence, the future of progressive politics looks pretty bleak. I can’t think of one formidable leader to run against our all-powerful eminence, should he choose to run for reelection.

God, I’ve got myself so depressed, I think I better have a drink. And I don’t even drink.

On other hand, here’s the deal on independent insurrections in Chicago—of which there have been exactly two that I can think of in the last century or so. You can have a strong, charismatic leader—think Harold Washington—who fires up the people to take on the czar.

Or you can have a situation as in 1979, when Jane Byrne came out of nowhere to beat the incumbent mayor, Michael Bilandic. Before she won, Byrne was pretty much written off as a kook who had no chance. Then came the snowstorms. The city’s inability to clear the streets stirred up a lot of resentment already simmering under the surface, especially in black communities.

These days, there’s a lot of resentment on the part of cops, firefighters, teachers, and other city workers—and even Reader writers. Not that anyone listens to them.

Until Mayor Emanuel shows a little humility—something to indicate he appreciates the impact of his policies on human beings—he’s his own worst enemy.

Maybe that’s the best we can hope for now that Junior’s left the scene.