Review ~ Making Obama

Eric Tang
Eric Tang
Sep 9, 2018 · 5 min read
Making Obama, from WBEZ Chicago

In May 1988, after two years as a community organizer, Barack Obama wanted something more. Over the last two years, he had won some notable victories. He’d successfully fought with the Chicago city government to preserve job placement centers in the South Side and clean asbestos out of project housing. But he felt restless.

“I want to produce more change than I think I can as a community organizer,” a friend would later recall Obama saying. So Obama decided that he needed to enter government, the institution he had often battled as a community organizer. But to enter government, he decided, he needed to become a lawyer. And to become a lawyer, he decided, he would apply to Harvard Law School.

Still, Obama fretted about this decision. He worried that he was selling out. “I thought that maybe I was betraying my ideals,” he would later say, “and not living up to my values.” So Obama went to speak to a trusted pastor, a man who had spent decades in the civil rights struggle. After speaking with him for a while, the pastor told him that if his heart was in it, he should go to Harvard. But, the pastor warned, “don’t let Harvard change you.”

Years later, in 1994, Obama tried to interpret his pastor’s words.

I think what he meant was, “Don’t forget the larger story that you’re a part of.”

He also meant, “Don’t misplace your dreams.”


This is just one of the gems from “Making Obama,” a beautiful six-episode podcast series from WBEZ Chicago. “Making Obama” tells the story of the former President’s early career, tracking his work as a community organizer and lawyer, his decision to enter political life, his failed and triumphant bids for state office, and his ultimate ascension to the U.S. Senate. Throughout, “Making Obama” seeks to understand Obama not just as a politician, but as a human character. We’re given a window to explore how Obama made connections, how he made some of the his most difficult choices, and how he grew as an individual throughout his life.

As a podcast, I can’t praise “Making Obama” enough. Host Jennifer White is an insightful, poised interviewer. The storytelling is brilliant, drawing suspense and tension from obscure chapters of Obama’s career. The podcast draws on source footage and interviews with dozens of Obama’s closest friends and rivals, and even Obama himself. The soundtrack bumps. Even the sound effects are gorgeous.

Obama and White in the WBEZ offices, 2018

But what strikes me most about “Making Obama” is the deeply human journey Obama takes: one of constant striving to make a difference in his community. Fellow community organizers said he was “the most serious young man,” constantly talking about “making a mark” on the country. In the statehouse, he often asked others, “Where can I make the most impact?” Grappling with his ambition, Obama tried to live out the advice of his pastor.

We hear a lot about Obama’s dreams for America. But as an individual, Obama also fought to place his dreams front and center.


Obama’s idealism comes through from the very beginning of his story. Two years after graduating from Columbia University, Obama decides to take a job as a community organizer in Chicago’s impoverished South Side. Keeping a low-profile, he pushes the city government to remove asbestos from project housing, keep a job training center open in his parishes, and divert more resources to the South Side. He earns $12,000 a year.

After two years of community organizing, the conversation with his pastor, the difficult decision to attend Harvard Law, and earning his law degree, Obama again faces a choice. As a graduating president of the Harvard Law Review, one of the most prestigious law publications in the nation, Obama has access to almost any job he desires. Yet despite offers from many of the country’s largest law firms, he decides to work at a small law firm focusing on civil rights legislation.

While working at the firm, he still feels unsatisfied, hoping to serve his community in a larger way. He runs for Illinois State Senate, winning a spot in the state legislature in Springfield. Yet in Springfield, he again grows restless. Tom Dart, a colleague in the state legislature, relates a conversation in which Obama vented his frustrations with the statehouse. “All of us are on this earth a limited number of hours,” Dart says, “and with that you want to be impactful, and I think both of us were very, very similarly of the opinion that this was not a place where you could be really impactful.” Riding this frustration, Obama decides to run for national office, running to represent Illinois’ 1st Congressional District.

Obama has crafted his career up to this point by never feeling satisfied. As a community organizer, then a civil rights lawyer, then a state senator, he strives to do good work — but he keeps feeling that there’s more he could be doing. I can’t help but hear the words of Obama’s pastor echoing at each of these turning points in Obama’s life.

Perhaps, though, Obama best follows those words when things go awry.


In his race with incumbent Bobby Rush, Obama suffers a rough defeat, losing by almost a two to one margin. He and Michelle are left almost $60,000 in debt. His friends worry that, with such a tremendous loss, his political career is over. And Obama himself wonders whether he’s making the right call to continue with politics; he ruminates about the financial stability he could have enjoyed in law.

Yet Obama takes another shot at moving beyond Springfield and, as he discussed with Dart, making a greater impact. He cobbles together a run for the U.S. Senate (against the advice of his friends, who literally laugh out loud when he proposes the idea). He wins. And the rest is, well, history.

I recognize that this feel-good story of an individual overcoming obstacles to succeed is simplistic. For almost every political winner, there is a loser; for every Obama, there are dozens of others who lose their races, derailing their ambitions to have a broader political impact. Obama also reckons with the toll that these political dreams take on his family, and he struggles to balance his political ambitions with his love for Sasha, Malia and Michelle.

Still, the story of Obama’s success is incredibly inspiring. Perhaps what I take away most from this podcast, the story of Barack Obama’s life, is that he remembered his dreams, even if achieving those dreams was improbable.

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