Imagine the following scenario: you're a well known, popular elected official who claims to be a champion of open, honest and reform-minded government. Imagine further that a long-time friend and member of your party who is also highly regarded as an advocate of reform is seeking to oust a three-term incumbent (also of your party) who is almost universally recognized as the worst type of old-style machine boss who has presided over a scandal-racked and patronage-ridden administration.

The political machine - the very establishment you've promised to challenge and change - is backing the incumbent for a fourth term. It is, as they say, business as usual. Yet your friend the reformer is running a surprisingly strong insurgent campaign and has a real chance of winning the primary.

What do you do? It should be no-brainer decision, right? You endorse the challenger and campaign to try and put him over the top, not just because he's your friend but because his election will help advance the causes you believe in and will, at the end of the day, benefit the citizens you both represent.

The scenario I've just outlined is a colorblind summary of Barack Obama's vantage point in the 2006 primary race for Cook County Board President between incumbent John Stroger and challenger Forrest Claypool.

But in Chicago politics reality is never truly colorblind, and political independence comes at a cost, which is why Obama could not bring himself to endorse his friend the reformer, Claypool, who is white, over the machine hack Stroger, who is black.

Instead, Obama remained neutral in the contest, and though this was seen by political observers as a tacit endorsement of Claypool, the question remains why Obama, who claims to be not of the political machine in Chicago and above the politics of race, could not muster up the political courage to make an explicit endorsement of Claypool during the campaign.

Jeff Berkowitz, host of a local public affairs television show in Chicago, put that question to Claypool recently. Here is the exchange:

Berkowitz: why couldn't [Obama] go that extra length? And, you know Barack. And, you've worked with Barack and you helped elect him to the U.S. Senate. So, it's not like he just knew you as a reformer. You folks - you've worked with David Axelrod's firm. You helped start David Axelrod's firm, AKPmedia, right?

Claypool: Correct.

Berkowitz: In 1984-85, and you worked closely with Rahm Emanuel, you knew Axelrod, you were sort of the Three Amigos, and maybe the fourth amigo was Barack Obama, why couldn't [Obama] go that extra length and endorse you? You could have been Cook County Board President. You could have seen reform [enacted]. You could have done a great many things that I know Barack Obama would like to do to improve health care and so forth for people in Cook County. Why couldn't he make that move?

Claypool: I don't know. I mean, look, politics is complex. People have multiple relationships and they do the things they have to do and believe in.

Politics is indeed complex, and most politicians "do the things they have to do" to look after their own personal interests - and Barack Obama is no different. In this instance, Obama's calculus in protecting his interests meant first and foremost showing deference to the Chicago machine, and also not making a move that would cost him support within the African-American community.

Claypool's remarks sounds eerily similar to the response Jeremiah Wright gave when Bill Moyers asked him how he felt about Obama distancing himself from the Reverend and his remarks:

He's a politician, I'm a pastor. We speak to two different audiences. And he says what he has to say as a politician. I say what I have to say as a pastor. But they're two different worlds.
I do what I do. He does what politicians do.

Whether Obama's endorsement would have mattered or not is beside the point. Endorsements are, as a matter of practical politics, mostly symbolism. By choosing to stay neutral in the race and to not go the extra distance to endorse Claypool, Obama signified that he was for reform and change - but only up to a point.

As it turned out, there was a bizarre epilogue to this race - and one that proves these kind of decisions have real world consequences. A week before the primary, Stroger suffered a severe stroke. The resulting outpouring of sympathy played at least some part in the final outcome: the reformer Claypool lost by six points, 53 to 47.

Stroger stayed out of sight for weeks and eventually it came to light that after recognizing he would not be able to stand for re-election, he engineered a deal from his hospital bed to install his son, Todd Stroger, on the ballot.

The move was decried by many, including Claypool, for what it was: a bald act of nepotism. Despite Todd Stroger's youth, inexperience, and his reputation as a corrupt, machine-style ward boss, Obama not only endorsed Stroger in the general election but heaped praise on him as a "a good progressive" - a claim that no one who knows him could make with a straight face.

In the end, Todd Stroger won election in November 2006. Since taking office as Cook County Board President, however, he has been an unmitigated disaster. With runaway tax increases and the county hospital system in crisis, Stroger has been busy packing the County payroll with allies at the expense of taxpayers, including more than a dozen friends and relatives making more than $100,000 per year.

One critic put it this way just a few weeks ago: "He [Stroger] is like a kid in a candy store handing out goodies to his buddies and his family members at a time when the average taxpayer is hurting." That critic was Barack Obama's good friend and the reformer candidate he didn't endorse for the job, Forrest Claypool.