"Power was patient and knew what it wanted," Obama writes about the post-Harold Washington era. Credit: Ashlee Rezin/for Sun-Times Media

As the days tick down on the Obama presidency, and with his so-called farewell speech at McCormick Place imminent, I find myself going back in time to the years when most people didn’t know his name—and those who did weren’t sure how to pronounce it.

I tend to get nostalgic when the past looks better than the future. And at the moment, the future looks awfully bleak.

Over the weekend, I re-read Dreams From My Father, Barack Obama’s best-selling autobiography. Initially, I revisited the book to help me think through Obama’s relationship with Chicago, and what his departure from office means for our city—especially since he’s not coming back here. And indeed, I found a lot of reminders that as much as Chicago loves to claim Obama as its own, he was never really ours.

But what surprised me on a second read of the book was the ways in which it’s eerily prophetic about the end of Obama’s presidency—prophetic in ways I’d never have imagined when I first read it way back when. But I’ll get to that.

If you haven’t read the book, I’ll set it up for you. Obama wrote Dreams in 1994. At age 33, he had just married Michelle and was making his way as a lawyer, already vibrant with big ambitions to show the world his stuff.

Much of Dreams describes his first stint in Chicago. He arrived in 1985 at the age of 24. He’d already lived in New York, California, Hawaii, and Indonesia. The son of a man from Kenya and a mother from Kansas was very much trying to figure out who he was, where he belonged, and what he wanted to do.

Obama settled in Chicago by happenstance. He wanted to be a community organizer and he couldn’t find a job anywhere else. So began his alliance with the Windy City as he took a job organizing in a poor, black community on the southeast side.

One of his favorite haunts was a Hyde Park barber shop he calls Smitty’s. He loved to listen to the old black guys talk politics.

This was in the middle of the Harold Washington years, when the black community declared that enough was enough, and rose up as one to elect Chicago’s first black mayor.

Unlike Obama, Washington was very much of this city, having been born and raised on the south side. And almost everywhere young Obama went—houses, churches, union halls, Smitty’s—he saw Harold’s picture on the wall. The “election had given [the] people a new idea of themselves,” Obama writes. “Or maybe it was an old idea, born of a simpler time. Harold was something they still held in common: like my idea of organizing, he held out an offer of collective redemption.”

I’m telling you, this stuff is prophetic—you could more or less say the same thing about Obama when he was first elected president.

In 1988, Obama temporarily moved to Boston to study law at Harvard. After he graduated in 1991, he came back. Why not? It was clear that his grander political ambitions required a clearer identity. He had to be from somewhere, so it might as well be Chicago.

“Power was patient and knew what it wanted. Power could outwait slogans and prayers and candlelight vigils.”

—Barack Obama about the post-Harold Washington era in Dreams From my Father

And so he turned himself into a pretty decent replica of a real Chicagoan for the decade or so he was here. It wasn’t that hard for him—he’s obviously a smart man who had the patience to listen to what people were saying. Like a sponge, he absorbed what he saw and heard.

He settled in Hyde Park. Joined a south-side church. Made the right liberal connections. Successfully ran for the Illinois state senate. He professed a loyalty to our sports teams, like he’d grown up rooting for them. He even became one of those insufferable Sox fans who dislike the Cubs, though he probably cared for one team about as much as the other—which is not very much at all.

Politically speaking, he was the quintessential Chicago liberal. He pushed hard for the right causes, like more school funding, but he knew enough to avoid direct confrontations with The Man—in those days, Mayor Richard M. Daley.

Was Obama’s Chicago conversion genuine? By my read, it was a little calculated. The epigram in Dreams, quoting Chronicles, sums it up: “For we are strangers before thee, and sojourners, as were all our fathers.”

It seems to me Obama was just passing through, on his own personal sojourn, looking to get out almost as he got in. In 2000, he unsuccessfully ran against Bobby Rush for congress. In 2004, he got out for good, getting elected to the U.S. Senate.

Did he use us? A little. Do I hold that against him? Hell no. He’s the greatest president of my lifetime—even if, OK, the bar’s kind of low. If Chicago was a means to an end, I’m glad to have been of service.

But that brings me back to the other prophetic part of Dreams—his recollections of the time just after Mayor Washington died in 1987.

With Washington dead, the same powerful remnants of the old Democratic Machine that Washington had kept at bay swept in to eventually elect Richard M. Daley. White Chicago vowed to never let a strong, independent-minded black man run this town again. And the black community, hopelessly divided, was powerless to stop them.

“Power was patient and knew what it wanted,” Obama writes about the post-Washington era. “Power could outwait slogans and prayers and candlelight vigils.”

In retrospect, young Obama sounds more jaded and less hopeful than he is today. “At the margins, Harold [made] city services more equitable,” he writes. “Black professionals now got a bigger share of city business. Harold’s presence consoled. . . . But beneath the radiance of Harold’s victory, nothing seemed to change.”

Substitute Obama’s name for Harold, and young Barack sounds like many young black activists today, critiquing Obama’s time as president.

According to Dreams, Obama went to City Hall to watch as the City Council met in December 1987 to approve Washington’s successor. On the way home, he writes that “the wind whipped up cold and sharp as a blade” and he saw a “hand-made sign tumble past me.”

“‘His spirit lives on,’ the sign read in heavy block letters,” Obama continues. “Beneath the words that picture [of Washington] I had seen so many times while waiting for a chair in Smitty’s barbershop . . . now blowing across the empty space as easily as an autumn leaf.”

Almost 30 years later, I feel much the same way about the country as Obama appropriately returns to Chicago to say goodbye to the nation. A sharp, cold wind is mercilessly threatening to blow away everything Obama worked so hard to achieve. Let’s hope the country does a better job of resisting than Chicago did after Harold died.   v