To grow up in or around Chicago in the late 20th century meant knowing the sound of Studs Terkel’s voice. Friendly, welcoming, unassuming, a little raspy, he hosted The Studs Terkel Program each weekday on WFMT from 1952 to 1997. Before political shows adopted professional wrestling as their discourse model, Terkel talked like you were sitting on a front stoop or in a pub booth with him. It’s the feeling that reporters want when they fly out to red states to talk to reg’lar folks at whatever local diner they think looks Americana enough for their Sunday readers. Terkel didn’t have to go anywhere to meet real people, because he saw the real in everyone.

Yes, OK, Terkel hung out on a stoop where James Baldwin, Oliver Sacks, or Lorraine Hansberry stopped by, but, as his WFMT archives reveal, he was just as happy to interview returning Vietnam War veterans in 1970, local architects, or his friend Saul Alinsky. Terkel had a genuine curiosity about what they thought, what they knew. Listening to his 1961 interview with James Baldwin, you hear the ease with which he engages Baldwin in an emotional conversation about Black identity and Baldwin’s struggle to finish his first novel abroad in Sweden. Compare that exchange to how awkward and tense Baldwin’s conversation with Dick Cavett is, or the adversarial mode mainstream reporters often forced on him—a posture that had to be dialed up to 11 for his debate with William F. Buckley Jr.

Former president Barack Obama’s new Netflix series Working: What We Do All Day brings Terkel’s legacy freshly to mind. It takes its name from Terkel’s best-selling 1974 oral history, Working. In it, he interviewed a wide range of people about their jobs, from bus drivers to newsboys to waitresses to executives. Obama and Terkel lived in Chicago at the same time, but their paths do not seem to have crossed much. Terkel died on October 31, 2008, at 96, just days before then-Senator Obama won the presidency on November 4. “I hope the election is a landslide for Obama,” he told Huffington Post contributor Edward Lifson.

When Lifson asked what Terkel would say if he interviewed Obama, he said, “I’d ask Obama, ‘Do you plan to follow up on the program of the New Deal of FDR? I’d tell him, ‘Don’t fool around on a few issues, such as health care. We’ve got bigger work to do! Read FDR’s second inaugural address!’” Terkel intuited something about Obama right away. “Community organizers like Obama know what’s going on,” he said. “So you know what? Obama can’t be a moderate! He’s got to remember where he comes from! Obama, he has got to be pushed!”

That advice certainly looks prescient now. A moderate to his core, Obama did focus on making the Affordable Care Act his signature legislation, but his bailout fell far short of what was called for, and he stayed in the center for most of his two terms. Terkel invoked FDR’s second address because he understood just how big the job before Obama was. That address came at a moment in January 1937 when the New Deal had made important strides toward improving the economic lives of Americans, but FDR knew it to be half-finished, and half-measures would not do. “Such symptoms of prosperity may become portents of disaster,” Roosevelt warned, as he urged the country to ensure that the reforms of the New Deal would be fully realized. “I see millions of families trying to live on incomes so meager that the pall of family disaster hangs over them day by day.… In this nation I see tens of millions of its citizens—a substantial part of its whole population—who at this very moment are denied the greater part of what the very lowest standards of today call the necessities of life.”

Sadly, FDR’s 1937 inaugural is as timely now as it was then. Obama’s Working series begins by evoking much the same plight, with struggling minimum wage and gig economy workers, then on up to the managers and CEOs. Obama uses the Hotel Pierre in New York as a recurring location. There, Working correspondents interview the hospitality workers, middle management, and finally its CEO, to illustrate how workplaces are an ecosystem—or food chain, depending on your position in the relevant divisions of labor.

The first episode opens with Obama walking through his own offices, greeting the members of his workforce by their names. In another, he delivers lunch to them—an example of the closer, beneficial relationship he argues we’ll need when addressing CEOs later who rarely meet their employees and even live on different continents. The far-from-subtle message here is that Obama is a good boss—which is no doubt true. Still, it’s important for the narrative logic of Working to defuse his privilege early.

The former president—who inked a $65 million deal with Netflix for documentary projects like this one—cannot but cast an outsize socioeconomic shadow over the proceedings. Unlike Terkel, he can’t take up an assuming position on a streetcorner or front stoop. The series makes sure we never see his Secret Service detail as Obama discusses the trials of making ends meet with ordinary workers. In these conversations, he is, as usual, charming and at ease with everyone—but here, too, the chasms of social class are unavoidable. In one segment, he goes grocery shopping with a home care worker who points out a $6 box of breakfast cereal and tells him how she only makes $10 an hour. At another point, he tells her that he’s met most of his goals in life, and that it’s future generations that he worries about. Six-dollar boxes of cereal versus shifting world economic safety nets for the working class: It’s another moment that would be unthinkable in a Studs Terkel broadcast.

The first and last episodes in the series work the best—but also illustrate the deeper tensions at the heart of the project. The introductory installment drives home the brutal facts of life in a starkly unequal American socioeconomic scene: that the stories of people working this hard and coming nowhere near a middle-class life represent a heartbreaking and unconscionable failure of moral and political will.

Meanwhile, the final episode, which focuses on CEOs as managers of this struggling workforce, tries to explain this tremendous failure and what to do about it. In one representative exchange, Obama talks to Jamsetji Tata, the owner of the Hotel Pierre, and lights up with the realization that Tata thinks about future generations, too! Both are big-picture people, and Obama draws Tata out on training workers for future opportunities.

It’s also in this episode that Obama the Great Explainer kicks in, using the rhetorical skills that helped him so much as president in breaking down complex ideas for us. Working spells out how Mississippi GOP Governor Tate Reeves has blocked $1 billion in Medicaid expansion for his state. This ideological blockade of desperately needed income support, Obama and his subjects stress, keeps the unsubsidized home care workers whom he interviews at the outset of the series—most of them women of color—chronically unable to make ends meet. It’s also here that Obama focuses on Home Care Mississippi’s heroic CEO Jeanette Felton, who has taken a large pay cut to keep her company and employees working.

In dissecting the current wealth gap between CEOs and their employees, Working presents footage of libertarian economist and renowned documentary explainer Milton Friedman preaching that the only goal of corporate enterprise is maximizing profits for shareholders. “I’m not in favor of fairness,” he says, “I’m in favor of freedom.”

How would Terkel have answered that? Perhaps with the same message he had for Obama in 2008: “The free market has to be regulated. And the New Deal did that and they provided jobs. The government has to. The WPA provided jobs. We have got to get back to that. We need more reg-u-la-tion.”

And how does Obama answer Friedman? He muses, “What if a CEO prioritized more than profit? There are different ways to lead. The CEO sets the tone. Their choices, their priorities, their values shape how people work together.” Like Jeanette Felton does, in other words. Working then returns serenely to platforming CEOs—Tata, and then Chris Urmson, who oversees Aurora, a company making driverless semitrucks he hopes will replace human truck drivers in the not-so distant future.

This maneuver is all too reminiscent of Obama’s own CEO-friendly handling of the fallout from the 2008 economic meltdown. Indeed, leaving these essential questions of economic fairness to a group of unicorn CEOs, implicitly charged with setting a better example for the troll CEOs, is little more than trusting in trickle-down economics. “The important thing is memory,” Terkel said in 2008. “You know in this country, we all have Alzheimer’s. Obama has got to remember his days as an organizer. It all comes back to the neighborhood.”

Obama has not forgotten, but he holds back, ever the pragmatist—just like when he was a president with a reelection campaign in front of him, a militant Tea Party backlash to contend with, and Mitch McConnell to outmaneuver in the Senate. Obama’s Working educates us on why our world shifted to where it is, but we are not in the participant-observer territory of Barbara Ehrenreich’s Nickel and Dimed here. That’s why Obama’s invocation of Terkel dissipates so quickly. It’s like Bruce Springsteen covering a Woody Guthrie song, or Aaron Sorkin making a Chicago 7 movie. It’s the frisson of radicalism repackaged by non-radical people. And it falls inevitably flat.

If he could, Obama would have a beer summit in Hyde Park with Milton Friedman and Studs Terkel, and most likely serve the beer himself. Terkel would be there, but he would not have changed much since his 2008 interview. “I was just watching Alan Greenspan. He’s an idiot,” he said then. “And by the way, so was Ayn Rand!”