Read these two articles:
The Agitator
Barack Obama (simply titled) at Obsidian Wings
Then get back to us.
Money quotes on the flip.
(Yeah, this is a short diary, and doesn't meet the guidelines. And it's also my first. Holy FSM, do I suck! However, I thought these two articles were highly informative, and were worth recommending for the attention of the wider community -- and in a way so that everyone who has been asking these questions (or as many as possible, anyways) can find it, as that seems to be quite a few.)
From "The Agitator":
In fact, Obama had already been applying Alinsky's core concepts--rigorous analysis of an opponent's strengths, a hardheaded understanding of self-interest as a fundamental organizing principle, a knack for agitating people to act, and a streetwise sense of when a raw show of power is necessary--to situations beyond the South Side. In 1988, Obama left Chicago for Harvard Law, where his greatest political victory was getting himself elected president of the law review. He did it by convincing a crucial swing bloc of conservatives that their self-interests would be protected by electing him. He built that trust during the same kind of long listening sessions he had made use of in the depressed neighborhoods of Chicago. ...
[...]
... Obama initially planned to inherit the seat of a much-admired incumbent named Alice Palmer, a fixture in South Side activist circles since the '60s. Palmer had opted to run for Congress, clearing the way for Obama to replace her, but, when she lost the primary, she decided she wanted to keep her old Senate seat, after all.
Obama was faced with a decision: step aside and wait his turn or do everything he could to take down a popular incumbent. In one meeting, an old guard of black political leaders tried to force Obama to abandon the race, but he wouldn't budge. Instead of deferring to Palmer's seniority, Obama challenged the very legitimacy of her petitions to get on the ballot, dispatching aides to the Chicago Board of Elections to scour Palmer's filing papers, and, while they were at it, every other candidate's, signature by signature. Many were fake. Obama won the challenge and cleared not just Palmer but all his potential rivals from the field.
It was a brash maneuver that caught the attention of the Illinois political establishment. ...
[...]
... The core question being raised today about Obama the candidate is whether he can be both a post-partisan, inspirational figure--the dreamer whom Wright first identified--and also the type of uncompromising political realist who can actually win. After all, the presidential campaign trail is littered with candidates, from Adlai Stevenson to Bradley, who, like Obama, bemoaned the dirty business that politics has become and tried to run campaigns that rose above the muck. Such candidates may maintain the high ground, but they always lose. Obama's assertion that he is, at heart, a community organizer suggests he might not fall into the same trap. He was, after all, trained to pursue the ideal but practice the pragmatic. Obama internalized the Alinsky maxim to always live in "the world as it is and not as we would like it to be," and, starting with his race against Palmer, he put it to use. In the world as we would like it to be, every election should have more than one contestant. In the world as it is, especially in Chicago, you challenge your opponents' signatures and knock them off the ballot.
[...]
"What I am constantly trying to do," he added, "is balance a hard head with a big heart."
Update: also an interesting find, to follow up on something mentioned in the article; from Wikipedia:
Alinsky was the subject of Hillary Rodham's senior honors thesis at Wellesley College, "There Is Only The Fight...": An Analysis of the Alinsky Model. Rodham commented on Alinsky's "charm," but rejected grassroots community organizing as outdated. Once Hillary Rodham Clinton became First Lady of the United States, the thesis was suppressed by the White House for fear of being associated too closely with Alinsky's ideas.
From the article at Obsidian Wings:
... There are a number of people I could imagine getting behind, and I'll decide which of them to go for when the election is closer, and the question a bit less hypothetical. But I do want to add one little data point while people are talking about him, because it's something I haven't seen people say. And it's this: a lot of people are going on about how Obama has not sponsored legislation on any of the Vital Issues Of The Day. Personally, I think that he'd have to be delusional to introduce, say, his own solution to the health insurance crisis: no bill on such a topic introduced by a freshman senator from the minority party would have a snowball's chance in hell of succeeding, and the only reason to introduce one would be to grandstand. For that reason, I think that his failure to do so tends to speak well of him.
[..]
But I do follow legislation, at least on some issues, and I have been surprised by how often Senator Obama turns up, sponsoring or co-sponsoring really good legislation on some topic that isn't wildly sexy, but does matter. His bills tend to have the following features: they are good and thoughtful bills that try to solve real problems; they are in general not terribly flashy; and they tend to focus on achieving solutions acceptable to all concerned, not by compromising on principle, but by genuinely trying to craft a solution that everyone can get behind.
[...]
... I can't remember another freshman Senator who so routinely pops up when I'm doing research on some non-sexy but important topic, and pops up because he has proposed something genuinely good. Since I think that American politics doesn't do nearly enough to reward people who take a patient, craftsmanlike attitude towards legislation, caring as much about fixing the parts that no one will notice until they go wrong as about the flashy parts, I wanted to say this. ...
[...]
As I said earlier, I am not interested in getting on anyone's bandwagon at the moment, and I wish he'd spoken up earlier about the torture bill. (Though the speech he gave on the Senate floor was excellent.). But I read one too many pieces about his lack of a track record, and I thought: clearly, the people who are writing these haven't had the same "there he is again!" experience that I have had while researching arcana. ...