Ryan Lizza's extremely detailed, 15000 word piece (in next week's New Yorker) on Barack Obama's Chicago life does a fantastic job of delineating the different forces in Windy City politics over the past twenty years. What was most interesting, however, was the way in which the piece explains Obama's simultaneous ability to criticize "the system" and operate within it. For example:

One day in the spring of 2001, about a year after the loss to Rush, Obama walked into the Stratton Office Building, in Springfield, a shabby nineteen-fifties government workspace for state officials next to the regal state capitol. He went upstairs to a room that Democrats in Springfield called “the inner sanctum.” Only about ten Democratic staffers had access; entry required an elaborate ritual—fingerprint scanners and codes punched into a keypad. The room was large, and unremarkable except for an enormous printer and an array of computers with big double monitors. On the screens that spring day were detailed maps of Chicago, and Obama and a Democratic consultant named John Corrigan sat in front of a terminal to draw Obama a new district.

And then:

In the end, Obama’s North Side fund-raising base and his South Side political base were united in one district. He now represented Hyde Park operators like Lois Friedberg-Dobry as well as Gold Coast doyennes like Bettylu Saltzman, and his old South Side street operative Al Kindle as well as his future consultant David Axelrod. In an article in the Hyde Park Herald about how “partisan” and “undemocratic” Illinois redistricting had become, Obama was asked for his views. As usual, he was candid. “There is a conflict of interest built into the process,” he said. “Incumbents drawing their own maps will inevitably try to advantage themselves.”

Ryan does not explicitly say so, but the politician this reminded me most of is none other John McCain. This is not true in the micro sense, of course, but McCain also has the ability to get away with typical "Washington behavior" (the number of lobbyists on his staff comes to mind) and decry the political system as broken. People are allowed to be conflicted and even hypocritical (would you rather have your politicians saying it was good that elected leaders drew their own redistricting lines, and celebrating our campaign finance system?), but this example--and others like it that the article details--are not going to endear Obama to the people who have been disappointed with his recent, political drift to the center.

Finally, and on a slightly more humurous note:

Obama had attracted a young and zealous corps of campaign workers. “I remember one of the candidates in the race used to talk about how crazed our volunteers were, because they were passionate, energized,” Will Burns said. “You’d come by the office on Eighty-seventh Street and there’d be a bunch of guys with no teeth waiting to get their next Old Grand-dad and then these Shiraz-drinking, Nation-reading, T.N.R.-quoting young black folk. 

--Isaac Chotiner