Ed Koch famously stopped New Yorkers to ask “so how’m I doin’?” Our mayor doesn’t do that, but we thought we’d do it for him, as a public service. We started by discussing Fran Spielman’s recent critique of the Mayor in the Sun-Times.

“I’m frustrated by him, and I think there’s a confrontational approach that’s not always necessary,” explains Sun-Times Editorial Page Editor Tom McNamee. “Certainly with the schools. I mean, just some sort of acknowledgement that teachers don’t get into this business to get rich, like most of his friends who fund his campaigns. That would be nice.”

But despite the frustration, McNamee says Emanuel was dealt a pretty lousy hand.

“When you’re running a big city,” he says, “and a big city that’s going down the tubes financially – I think it’s accurate that he’s going to have a one billion dollar pension deficit in a year and a half – when you run a big city where the population’s been in decline for a couple of decades and the school scores are in the basement, and were in the basement before you came in, and where the crime rate was 600 people murdered well before you came into office…I would ask people, find me the mayor who, in about two years, can do anything about that and look like a hero.”

Our conversation, which also includes Chicago Magazine’s Carol Felsenthal, turns to the inevitable comparison between the current mayor and the one before – the one he never names. That former mayor, we observe, seemed to be a long-range thinker and planner. Someone who had a vision of what he wanted Chicago to be in ten or twenty years. Emanuel doesn’t appear to think that way.

“He doesn’t have time to be a dreamer,” says McNamee. “He has to figure out how to pay the bills.”

Yes, we add, and in the last four or five years, Mayor Daley (see, we named him) didn’t have time to be a dreamer, either.

“No, he didn’t,” agrees McNamee, “which is why Rahm’s stuck. Because Daley was looking the other way while we were going further and further into debt, building up these pension obligations and not paying them. Maybe if Rich had been a little more like Rahm we wouldn’t be in this spot right now.”

That said,” he continues, “I think Rahm’s model is all these venture capitalists who think they can fix the world because they learned how to get rich. I think he’s surrounded by people who have great wealth…and now they’re sitting in these incredible high-rises, in Trump Tower or wherever they live – on Astor Street – and they’re talking about, my God, I could fix that school. Let me go to it.  I think he’s enamored of that world of people, and he sort of buys into the idea that if you can create this wonderful big business you can fix anything. And I think what he’s finding out now is, it doesn’t work that way.”

Speaking of businesspeople wanting public office, Mayor Emanuel might have divided loyalty in the upcoming governor’s race.

“Rahm is working, clandestinely, to raise money for his friend Bill Daley,” Felsenthal asserts. “I thought he was raising money clandestinely for Bruce Rauner, his other friend. In fact, the Emanuels and the Rauners have vacationed together. They are more than just casual friends.”

“But the Bill Daley connection is a very interesting one,” she says, because it might be helpful to Emanuel in the future. “The Chief of Staff job, the helping Rahm get into this Mayor job so he can get the executive experience that he needs to move on…maybe start out in the V.P. slot…”

But can Bill Daley beat Pat Quinn in the Democratic primary?

“I’m waiting for the Daley press conference where he tries to attach the $700,000 copper clad Capitol doors to Quinn,” she says. “Quinn was the person in charge. It went by his desk.”

A quick summary of our panel’s current take on the Governor’s race: Quinn can beat Daley. But if Rauner emerges as the Republican candidate – and polling indicates that’s a long shot – he can beat Quinn.  But Rauner has a tougher time against Daley, who’s also a successful businessperson, but with greater name recognition.