Emanuel took to the digital world from a place that has been an example of the digital divide: Chicago's South Side.
The mayor headed to Kennedy-King College where students and citizens connected at one of three watch gatherings to tune into a talk about the Emanuel agenda. That's not unusual in itself, but what stood out was the manner in which the whole transaction took place. It was another example of an old saying: "The medium is the message."
Emanuel hopped onto a small set and prepared for an onslaught of questions from those watching via Facebook and Livestream.com. Over 500 watched the live video stream.
The mayor tackled the range of municipal challenges Chicago faces, including managing the city's finances, to school reform, and telling gangs they don't own the streets.
"That to me is what the city hired me to do," Emanuel sad.
For Pierre Jones, a 12-year-old participant in the Digital Youth Network Program, part of After School Matters, being here was proof that his decision to pursue his interest in computers was sound -- even if Emanuel did not answer his concerns about gentrification as a solution to the Englewood neighborhood's troubles.
"It's not really right because we were watching him over the video but the video skipped sometimes, so I think he should be here in person," Pierre said.
April Lawson employed her digital literacy skills obtained through the federal government's Smart Communities Program. The $7 million initiative program puts computers and digital training in five neighborhoods on the South and West sides. The town hall worked in a way she didn't expect.
"You got this sub story going on in the bar, where you're actually communicating with the other people that are asking questions, so it's cool," said Lawson. "You've got the conversation with the mayor, and then you've got the conversation with other unknown people that are a part of this town hall meeting as well."
The hour online was not without its buffering issues, but the mayor emerged saying the experience sharpened him, and whet his appetite for more such encounters.
"It's easy in city government to get lost in the details and what I think is important," said Emanuel.
On Monday the mayor held a telephone town hall that analysts said featured a lot of softball questions. Thursday's Facebook encounter seemed a lot tougher, with pointed questions, especially about the mayor's threat to lay off 625 employees if unions don't agree to work-rule changes.
You can watch an archived video of the live chat here: http://www.livestream.com/chicagomayorsoffice