Please skip to the last paragraph for the Conclusion. As context for those who don't know Chicago, I use personal anecdotes, wiki links, demographics, an example of Hillary Clinton's experience, and the chilling, unfortunate conclusion.
Chicago, Illnois
Like Barack Obama, I moved to Chicago after college. Unlike Hillary Clinton and Barack Obama, I only lived in Chicago for a few years.
Chicago is an amazing city--very diverse and very prosperous. A not-so-well-hidden secret is that it's also amongst the most segregated cities in the US. It's still not uncommon to have areas that are 98% White or 98% Black, sometimes next to each other. The implications of the moniker South Side move well beyond race into poverty, social justice and equal opportunity. Historically, the South Side allowed impoverished communities (Polish, Irish, Black, etc.) to form a middle class and an upper class in a manner not often possible in other areas of the country. The South Side of Chicago and Harlem are, arguably, the two areas in the country to afford blacks this opportunity in the early and mid-20th century. I moved to the West Side of Chicago in 1998, an area that is considered integrated. Racially (Indian), I was in a unique position to see the impact of segregation at the turn of the new century.
In my first week, I went jogging through my neighborhood on a quiet Saturday morning. Moving from Oregon, I was used to saying 'hi' when I came across strangers along the street. My immediate neighborhood had tennis courts, trees, flower beds, and plenty of security. In the first few blocks I was stopped and asked for money twice. The second guy said something fascinating. "You don't need to be afraid, your skin is almost as dark as mine." We did a quick color match of our forearms and my "brown" skin was actually several shades darker than his "black" skin. I learned that black and white in the Chicago context are not about melanin content or race but social constructs. I told him I was sorry I didn't have change, wished him a good morning, and kept jogging. A few blocks over, it was a stereotypical ghetto from the movies. Abandoned buildings and busted out windows. When I was stopped in this neighborhood, I wasn't asked for change, but instead offered drugs and hookers.
Over the years, I found that my dark skin meant that I could often "pass" in the black community. But not always. Once, while walking through Washington Park , I went by a group of young girls skipping rope on the lawn. By this time I was used to not making eye contact or saying 'hi' to people. Still, a 12-year old stopped me and asked me... "where are you from?" I told her the West Side. Think about that, a 12 year girl in 1999 living 1 mile from the Univ of Chicago hospital (probably 10-20% Indian plus hundreds of other ethnicities) was completely confused about my race. But, there was no malice in her thought. This is the history of segregation in our country today. When I volunteered for a program to take local kids from a housing project to the museum, for many (maybe 50% or more) of the 7 to 14 year olds it was literally the first time that they saw Lake Michigan 4 miles away. Conversely, most of those who I knew in their early 20's who were white and had grown up on the North Side or the suburbs, could count on one hand the number of times they had been to the South Side. They usually had the money and the opportunity, but simply never had the need, except if they were affiliated with the Univ of Chicago or possibly to go to a White Sox game.
Hillary Clinton
Hillary Clinton knows Chicago. She grew up in suburban northwest Park Ridge. Park Ridge's 2000 demographics were 95% White, 0.2% Black, with 2% below the poverty line. Clinton tells a story of how her dad would take her through "skid row" when she was a kid (possibly the area where I lived on the West Side) . Hugh Rodham wanted her "to see what became of people who, as he saw it, lacked the self-discipline and motivation to keep their lives on track"). Hillary Clinton knows the exact connotations of accusing an opponent of being under the influence of a slumlord from the South Side.
Jeremiah Wright made offensive comments about the Clintons that should be rejected. Jeremiah Wright made inflammatory comments about government policy that have been distorted by Sean Hannity and now Hillary Clinton as "hate speech". Jeremiah Wright made paranoid comments about conspiracy theories that could be laughed at or regarded with historical perspective. Some of these comments are a political liability. Barack Obama denounced all of these comments and he went further. He opened up the dialogue in a nuanced and substantive way to include his church, his pastor, his grandmother, and his country...a dialogue about generation, race, class, and community. Hillary Clinton knows that Barack Obama is bi-racial, and to state the bluntly obvious, Jeremiah Wright could have even more significant European ancestry. Hillary Clinton has heard of the one-drop rule. The context of black used in Chicago, in this church, and in this country is not exclusively racial. TUCC is not a black separatist church that engages in hate speech. If Hillary Clinton had evidence that it was, she should have provided it first. I'm sure Newsmax would've been happy to publish it for her.
Conclusion
To use the favorite metaphor of Clinton supporters, Hillary Clinton threw the entire city of Chicago (plus a lot of other things) under the bus. As her vehicle she chose Richard Scaife and her words echoed Sean Hannity. And, she claimed to have had "fun" while doing it.