Two class-action lawsuits filed after the protest allege a violation of constitutional rights - one involving 16 people who were arrested, and another larger one involving more than 500 who were taken into custody that night in March 2003.
The smaller of the two lawsuits is on the verge of a financial settlement with the city. That group of protesters, who in some cases spent more than two days in jail, could receive settlements between $10,000 and $20,000 per person.
In the larger class action, if the city settles or loses at trial, it will cost the city millions.
The protest began as an anti-Iraq war demonstration at Federal Plaza and then morphed into a march. Protesters - the loose estimate was 10,000 of them - walked north, stopping traffic on Lake Shore Drive, then west on Chicago Avenue, where they were essentially corralled by police and not allowed to leave, the appellate court later concluded.
"There was no indication that the Chicago Police Department wanted the demonstration to end. Indeed, they surrounded and arrested people and that's the way they shut it down," said Joey Mogul, People's Law Office.
"I definitely didn't deserve to sit in jail for two nights," said Steven Hudosh, who was among the protestors that night. "There were plenty of people who wanted to go home?I ended up sharing a cell with people who'd wondered out of their hotel rooms and weren't even part of the march, and ended up in the fray."
Over 500 people were arrested. Two class-action lawsuits were filed. The Emanuel administration wants to now settle them especially after Federal Appeals Court Judge Richard Posner last year ripped what he called the "idiocy" of the city's protest rules, requiring a permit, but then police allowing a march without one, while not having a plan to disperse what had been a largely peaceful crowd.
"The failure to settle the lawsuits has only driven up the cost because we've had seven to eight years of litigation and attorneys' fees which will mean millions in damages paid to people whose rights were deprived," said Ald. Joe Moore, 49th Ward.
One of the class action suits is near settlement, the second, larger one is in negotiation, and if that fails, trial starts in a month. But those on both sides of the dispute say CPD crowd control has changed significantly since the night on the Drive.
"I thought the police department listened in the Occupy arrests. We'll see if that continues in the G-8/NATO meetings. We'll see," said John Stainthorp, People's Law Office.
The class-action suits have played a role in how police have handled more recent large protest gatherings. And the thrust of the court's message has been - if a large gathering turns into a march, and police permit it, they have to be very clear on - on loud spearkers so all can hear - where the marchers will be allowed, as well as when and how they disperse. In other words, there has to be an end game that clear's to all.
The protesters from nine years ago say the direction they got came when the arrests started.