Being from the Chicago area and having written about Chicago politics off and on since I began this site, many bloggers, reporters, and radio hosts have asked for my thoughts on the relationship between Barack Obama and the Chicago political Machine. Invariably, my answer is necessarily shallow and incomplete because in order to do justice to the question, many aspects of his relationship to parts of the Machine must be fleshed out while other connections must be found to the reformers and their allies. In short, there is no easy answer to the question of Barack Obama’s status as a Chicago politician and trying to pigeonhole him as Machine hack or courageous reformer just doesn’t tell the whole story.

That’s because overall, the one thing that informs Obama’s career – the one defining characteristic of his rise has been an overarching ambition to achieve high office. This has forced him to make alliances with individual Machine politicians like Illinois state Senate Leader Emil Jones and fixers like Tony Rezko. At the same time, he has kept one foot firmly planted in the reformers camp, running for the state senate out of a district that elected legendary reformer Alice Palmer while occassionally talking the talk of an anti-Machine crusader.

How does he get away with it? Obama is a very clever, very tough, very shifty politician as we have seen these past 17 months. He is both of the Machine and an outsider. And the thing that makes these seemingly disparate parts whole is the engine of his ambition. Whatever suits his plans at the moment is what determines where he comes down on an issue or a personality.

It has been fascinating to watch Obama supporters try and defend Obama’s cozying up to the Machine over the years. They refer to “building bridges” or “reaching out” to all factions in order to pass a bill. This paean to Obama in today’s Washington Post by author of the V I Warshawski crime novels Sara Paretsky that purports to “explain” Obama’s Chicago career is an example of what I mean:

Like me, Barack Obama arrived in Chicago with high ideals and a passion for social justice. Unlike me, he found that his road does lead through electoral politics. One of my novels, “Burn Marks,” shows how an idealistic person can be squeezed by the political process. In that book, my fictional president of the county board, Boots Meagher, gets involved in an arson-for-hire scheme that leads to murder and almost gets V I Warshawski killed when she investigates. At the end of the novel, after V I gets too close a look at the lengths to which some people will go to keep the right friends friendly, she gets a key reminder from an old pal: “This is Chicago, sweetheart, not Minneapolis.”

That book presents a snapshot of the most sordid aspect of Chicago and Cook County politics, but I believe that Obama has found a way of threading the needle between working with the established powers and maintaining a commitment to social justice. He ran for Congress in the 2000 primary against four-term incumbent Rep. Bobby Rush. He steered clear of the key players in the Illinois Democratic Party to run as clean a campaign as possible, and he lost resoundingly. Since then, he has built essential bridges without seeming to have lost his integrity.

“Threading a needle” is a misnomer. Obama’s “commitment to social justice” is exactly as deep as it needs to be at the moment. And if his stand on an issue like abortion or gun control causes problems, he simply changes it and then claims he never did – even in the face of quotes from speeches that make him out to be a liar. It is breathtaking. And it is shameless. But it has stood him well over the years.

And Paretsky is laughably uninformed of she believes Obama eschewed endorsements from the Machine in his 2000 race against Bobby Rush in order to run a “clean campaign.” The fact is, Rush had all the major endorsements locked up already, giving Obama, who would have killed for an endorsement from Jones, Stroger, or Daley himself, nowhere to go for major support but the weak and ineffective reformers he had been lukewarm toward for 4 years. Obama lost badly and took away a valuable lesson in defeat; next time I run I’m going to have the Machine in my corner.

Enter Emil Jones, long time Democratic leader of the state senate and the consummate Machine insider. The story of how Obama came to run for the United States Senate is revealing not only of Obama’s overweening ambition but also of his unadulterated gumption when his own career is at issue.

The story, perhaps apocryphal, has Obama walking into Jones’ office following the ascension of the Democrats to majority status in the state senate for the first time in 26 years in 2002. The way Jones tells it, Obama told Jones he had “the power to elect the next senator from the state of Illinois. Jones responded, “Do you know anybody I could make a US senator?” Obama reportedly replied “Me.”

Rather than kick the young whippersnapper out of his office on his ear, Jones chuckled and spent the next year building Obama up. How did he do that?

When asked about his legislative record, Obama rattles off several bills he sponsored as an Illinois lawmaker.

He expanded children’s health insurance, made the state Earned Income Tax Credit refundable for low-income families, required public bodies to tape closed-door meetings to make government more transparent and required police to videotape interrogations of homicide suspects.

And the list goes on.

It’s a lengthy record filled with core liberal issues. But what’s interesting, and almost never discussed, is that he built his entire legislative record in Illinois in a single year.

It was Jones who attached his name to those 26 pieces of legislation. And it was Jones who also gave Obama some other high profile issues to shine on:

Jones further helped raise Obama’s profile by having him craft legislation addressing the day-to-day tragedies that dominated local news headlines.

For instance, Obama sponsored a bill banning the use of the diet supplement ephedra, which killed a Northwestern University football player, and another one preventing the use of pepper spray or pyrotechnics in nightclubs in the wake of the deaths of 21 people during a stampede at a Chicago nightclub. Both stories had received national attention and extensive local coverage.

Obama supporters never mention why Jones might have been so forthcoming in his support of this unknown state senator who had been shellacked by 30 points in his one campaign for higher office. The idea that a Machine insider would do anything for anybody without expecting something in return is ludicrous. So just what did Jones want from Obama?

Last June, to prove his commitment to government transparency, Obama released a comprehensive list of his earmark requests for fiscal year 2008. It comprised more than $300 million in pet projects for Illinois, including tens of millions for Jones’ Senate district.

Shortly after Jones became Senate president, I remember asking his view on pork-barrel spending.

I’ll never forget what he said:

“Some call it pork; I call it steak.”

Spoken like a true Chicago pol.

We see a similar pattern of behavior in his relationship with Tony Rezko, the convicted fraudster and political fixer who took Obama under his wing when he was a young attorney working at Davis, Miner, Barnhill & Galland, a small but well connected law firm that was assisting Rezko and his associates with getting city and state contracts to rehab low income housing.

The relationship with Rezko is perhaps the most complex of Obama’s life. Rezko was apparently the initiator of many of the contacts between the two. While Obama mostly saw Rezko for what he was – someone who could do him a lot of good when it came time to run for office. Were the two men friends? In the tangled world of Chicago politics, it would be more accurate to say that the two were “associates.” Rezko almost certainly annoyed Obama at times with his efforts to get closer to the young man while Obama, clearly seeing electoral consequences with getting too chummy with a character like Rezko no doubt tried at times to keep him at arms length.

We see this most clearly in Rezko helping Obama acquire his mansion. It seems unbelievable but apparently, Rezko did indeed show up almost out of the blue with an offer to buy the vacant lot next door to the mansion thus making it possible for Obama to save around $600,000 on the purchase price. The sellers of the house have confirmed as much as they also confirmed that there were no other bidders on the property. This is not out of the ordinary in that Rezko was, as I said, usually the initiator of contact between the two. For his part, Obama would then use Rezko as a bundler for his political campaigns as well as using Rezko’s extensive contacts in the Chicago real estate development community to meet others who could shake the campaign money tree.

Obama used Rezko’s “generosity” in order to buy his dream home even though at the time, Rezko was being investigated for the crimes that are sending him to jail and Obama knew it. What did Rezko want in return? Continued access to Obama is certainly one price the senator paid for Rezko’s largess. There is some evidence that came out at the trial that Rezko was in contact with Washington lawmakers, trying to get them to intervene with the State Department who had denied a visa to one of Rezko’s business partners, billionaire Nadhmi Auchi. Obama denies he or anyone in his office contacted Foggy Bottom on behalf of Auchi or Rezko but such interference is common and there would be little evidence of it anyway.

So the question of why a “reformer” would be hanging around with a shady Chicago fixer answers itself; because both men found they could do each other a lot of good. For years, Rezko was Obama’s goto guy for campaign money while Obama worked diligently at the state level to steer lucrative rehab and other contracts to his associate. Perfect political symbiosis and very revealing of Obama’s working with the Machine whenever doing so would help his career.

What do the small group of dedicated Chicago reformers think of Obama? The one word that continually escapes their lips when describing Obama is “pragmatist.” On several high profile issues, Obama has indeed supported them – if rather tepidly at times. But on some key endorsements, Obama has chosen to back the Machine hack rather than the reform candidate. The case of Dorothy Tillman is instructive. A corrupt, hard nosed woman, she was famous for drawing a gun in a city council meeting. The reformers put up an excellent, well qualified candidate to run against her in the Democratic primary:

Just three months before Obama made his endorsement, the Lakefront Outlook community newspaper ran a three-part investigative series exposing flagrant cronyism and possible tax-law violations that centered on Tillman and her biggest pet project, a taxpayer-funded cultural center built across the street from her ward office that had been hemorrhaging money since its inception.

In the end, Tillman lost the election despite Obama’s endorsement, which critics said countered his calls for clean government. Obama told the Chicago Tribune that he had backed Tillman because she was an early supporter of his 2004 U.S. Senate campaign.

Tillman was also a close ally of Mayor Daley and Cook County boss John Stroger – two men who Obama absolutely needed on his side in his run for the presidency. Indeed, Obama also endorsed Daley himself, proclaiming that city hall had been “cleaned up” thanks to the Mayor’s efforts. The rank cynicism of saying that he was endorsing the man who made city hall a cesspool of corruption in the first place was visible to anyone who cared to look.

The fact that both sides in this debate over Obama’s ties – or lack of them – to the Machine have ammunition for their arguments should tell you a lot about how Obama has managed this sticky, complicated relationship over the years. But there is little doubt that he was nurtured by the Machine, cut his teeth using the tactics of the Machine – as when in his first state senate race, he had all the other candidate’s ballot petitions thrown out by challenging the signatures – and in the end, allowed the Machine to embrace him as their candidate for president of the United States. Many of his top campaign aides are connected to the Machine in one way or another. And, of course, he moved his campaign headquarters from Washington to Chicago which no doubt pleased Mayor Daley.

The biggest question I have is will this complex dance with the Chicago Machine continue if Obama wins the presidency? What’s the payoff for Daley and his cronies? To believe that those fellows support a candidate out of altruism is loony.

And maybe its time the American people started asking themselves the same question.