For me, there is nothing more exciting about the Obama’s presidency than his decidedly urban lifestyle. I am particularly captivated by the thought of him using his current residence on the South Side of Chicago as his place of retreat from the hustle and bustle of 1700 Pennsylvania Avenue in D.C.

As a child of urban environments, imagine my glee when in a recent interview with the Chicago Tribune Obama made it abundantly clear as to where his place of retreat would be. “MyKennebunkport is on the South Side of Chicago,” he commented.

Kennebunkport (Massachusetts) by the way was the preferred hideout of former President George HW Bush. And of recent times, his son George W. Bush found solice in a town called Crawford, Texas, likely the last place you’d find someone like Obama wanting to hang out. Of course, Obama will have access to Camp David, the U.S. Presidential retreat nestled away inCatoctin Mountain Park in Maryland–a place that somehow that just doesn’t seem like his cup of tea in terms of the urban culture he has grown so comfortable with.

But the South Side of Chicago? Anyone who hails from the Windy City knows that this part of town conjures up some interesting opinions depending on what side of the tracks you grew up on. For many, the South Side symbolizes a lower class, industrial, crime-riddenoaisis of abandoned houses and shuttered up school buildings. It also carries the vestiges of segregation–a reality that has lead many urban experts to mint Chicago as the most segregated major city in the United States. It short, thecliffnote version reads as follows: People of color are expected to live on the south side of Chicago while others live on theĀ  preferred north side.

I recallĀ  an African-American friend of mine, a radio station executive, who was moving from Washington D.C. to Chicago a few years ago calling me in total disgust over his realtor insistence on him touring homes exclusively on the South Side. As a Chicago area resident at the time, I shared with him some of the unfortunate realities he would face in a city where these sort of perceptions run rampant.

Enter Obama’s neighborhood. Known as the Hyde Park-Kenwood area, it is often affectionately referred to the “Other South Side” to people who are familiar with it. Uniquely diverse in it’s racial, ethnic and cultural makeup, it features million dollar homes surrounded by some of the city’s most impoverished neighborhoods. Home of the University of Chicago, an Ivy league calibre institution, the area attracts many high brow intellectuals who find comfort in a diverse community brimming with progressive ideas.

Obama first moved there in the early 80’s as a community organizer and then returned once again after attending Harvard Law School. He then met his wife Michelle who grew up in the nearby South Shore neighborhood. Word has it that they shared their first kiss at the Hyde Park area Baskin Robbins located at 53rd and Dorechester.

But why would Obama chose this as his place of retreat when he has so many more remote, low profile locations at his disposal? Because Obama is truly urban at his core–his family ties, homeboys, local gym, and barbershop are all a part of the Hyde Park-Kenwood neighborhood he will always call home. This is the area where he established his reputation as a community organizer; where he and Michele built a wonderful family. As I see it, his desire to stay connected with the neighborhood that brought him this far, and that he is most comfortable with, will allow him to make history as the most urban engaged President in our nation’s history.

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