The group’s chairman took this all in, then offered the all-too-predictable response. “Yes, yes, we noted that,” he said, according to the colleague. “We have five other objections.”

The Obama era has been deeply disorienting for the left. Eight years ago, progressives would have delighted at the idea of a president who withdrew from Iraq, remade the rules for Wall Street, slowed the proliferation of greenhouse gases, brought the country within spitting distance of universal health care, and multiplied the rights of gays and lesbians. And yet it’s hard to be a self-respecting progressive these days and not feel a frustration that borders on disillusionment. The victories have been muddled, the errors unforced, the ambitions preemptively scaled back.

How could these two legacies coexist in one presidency? They emanate from the worldview that Jarrett and Obama share—call it “boardroom liberalism.” It’s a worldview that’s steeped in social progressivism, in the values of tolerance and diversity. It takes as a given that government has a role to play in building infrastructure, regulating business, training workers, smoothing out the boom-bust cycles of the economy, providing for the poor and disadvantaged. But it is a view from on high—one that presumes a dominant role for large institutions like corporations and a wisdom on the part of elites. It believes that the world works best when these elites use their power magnanimously, not when they’re forced to share it. The picture of the boardroom liberal is a corporate CEO handing a refrigerator-sized check to the head of a charity at a celebrity golf tournament. All the better if they’re surrounded by minority children and struggling moms.

Notwithstanding his early career as a community organizer, Obama, like Jarrett, is fundamentally a man of the inside. It’s why he put a former Citigroup executive and Robert Rubin chief of staff named Michael Froman in charge of assembling his economic team in 2008, why he avoided a deep restructuring of Wall Street, why he abruptly junked the public option during the health care debate, why he so ruthlessly pursues leakers and the journalists who cultivate them. It explains why so many of his policy ideas—from jobs for the long-term unemployed to mentoring minority youth—rely on the largesse of corporations.

It’s the boardroom liberal in Obama who gets bent out of shape over criticism from outsiders, despite having once urged progressives to press him the way civil rights activists like A. Philip Randolph pressured Franklin Roosevelt. He is a president profoundly uncomfortable with populist rhetoric. He prefers to negotiate behind closed doors, as he did on the stimulus, health care, and deficit reduction, rather than wage a state-by-state political campaign to force concessions. Except for a handful of moments over the last six years—like when the administration tried to pass a second stimulus bill known as the American Jobs Act—Obama has rarely tried to mobilize public opinion in any sustained fashion. He has been consistently slow and half-hearted about taking unilateral action.

Bill Clinton was in many ways more conservative than Obama, whom you couldn’t imagine signing a draconian welfare law, or an anti-gay-marriage law, or, for that matter, de-regulating Wall Street. But Clinton was not above riling up voters for partisan gain. By August of 1995, the year Republicans took over Congress, Clinton and his surrogates were flogging them daily over “Medicare, Medicaid, education, and the environment.” When Republicans retook the House in 2011, Obama spent most of the year shunning partisan taunts in hopes of consummating a grand bargain. And Jarrett was there at his side, amplifying those sensibilities. “The context for that is that it’s consistent with who the president is,” Jarrett’s first-term chief of staff, Michael Strautmanis, told me. “She has only one agenda. And it is the president’s agenda—either from conversations he’s had with her, what she’s heard him say, or based upon their history together.”

As it happens, the way the White House runs these days does even less to check Obama’s inclinations. According to a former high-level aide, there is no longer a daily meeting between the president and his top advisers. Under the old system, if the president waved off one adviser’s objection to his preferred plan of action, another could step in to vouch for the objection’s merit. The advice Obama gets now, though, comes more regularly through one-off interactions with the likes of Jarrett and Denis McDonough, who don’t have anyone else to back them up. In the second term, observes the former aide, “Maybe the president says, more often than in the past, ‘We’re doing it.’”

The result is that Obama has become even more persuaded of his righteousness as the years have gone on. His belief that he can win over opponents is unshaken. Unfortunately, these opponents include a party in the throes of radicalism and a self- interested class of ultra-rich that increasingly calls to mind plutocracy—not people whose better instincts you can appeal to. Obama and Jarrett should know this. Any time they have made preemptive concessions to the GOP or business leaders, their negotiating partners have simply pocketed the concessions and asked for more. From the budget battles to immigration reform, they have consistently overestimated the ability of Republican elites to reason with their rank and file. As recently as early this year, the official White House position was that it preferred Congress to ban workplace discrimination against gays. Congress!

Perhaps no episode illustrates this mind-set better than the fate of the consumer agency that the Dodd-Frank financial reform bill created. In 2010, Jarrett and two other advisers persuaded Obama to install a genuine populist in the person of Elizabeth Warren to set up the agency. But they never intended for her to actually run it, a promotion Warren aggressively sought. “Having Warren in the short-term role was their elegant solution,” says a former administration official. “It was the best way to appease the left while preserving [Obama’s] reasonableness to business. That’s what drives him: Do they look reasonable? ... That’s what Valerie’s all about.”

It’s no surprise that Barack Obama and Valerie Jarrett would govern as reasonable people. It’s who they are. The tragedy is that we live in surpassingly unreasonable times.

CORRECTION: This story initially said that Donna Brazile "limited her kvetching to private phone calls and struck her best 'we’re all in this together' posture" during the Shirley Sherrod episode. It has been corrected to better reflect her comments.