AFL-CIO policy director Damon Silvers is concerned about the status of the American labor movement. (Linda Davidson/The Washington Post)

Damon Silvers still remembers the pickles. In 2011, at a roundtable discussion in Durham, N.C., the President’s Council on Jobs and Competitiveness showcased biotech firms that weren’t planning to hire anybody, remnants of the textile industry, and an artisan pickle maker. Silvers, the policy director of the AFL-CIO, concedes that the jobs council was celebrating some wonderful entrepreneurial people. But really, he says, it was evidence of a collapsing industrial economy and a president who seems to have given up on pushing a comprehensive progressive agenda.

“If we become a society of a handful of biotech engineers working for companies that are going to move jobs overseas and the rest of us are fighting for jobs stuffing pickles into jars, that’s not the kind of place you want to live,” he says.

Silvers doesn’t want any of us to live in that kind of place. But the labor movement is as weak as it has ever been, with the percentage of American workers who are union members at an all-time low of 11.3, mostly concentrated in the public sector. Instead of signing up for a long career as an auto worker or a coal miner, more people now work on contract for no benefits, rupturing the relationship between labor and management that unions had evolved to exploit. On top of that, long-term mass unemployment means that nobody’s willing to demand anything from an employer other than a steady paycheck.

Silvers, a 49-year-old lawyer with three Harvard degrees and Coke-bottle glasses, is the person who’s supposed to stop the unions’ free fall.

Here’s Silvers’s problem: Even if the American working class does recover some strength, he knows that his 70-year-old employer — which represents everyone from the United Auto Workers to National Nurses United — may not be the one to capture it.

“I believe that working people will not allow themselves to be treated as objects forever. The question is not whether that will change, because it will,” Silvers says, in between bites of a veggie burger he’d grabbed from the AFL-CIO’s small cafeteria. His disheveled seventh-floor office overlooking 16th Street just north of the White House looks more like a landing pad for memos and reports than an actual place to work; the walls are nearly empty but for an image of Sen. Elizabeth Warren taped up with the slogan “Yes She Can.”

“The question is, what is the relevance of these historical institutions that working people built in the past?”

Silvers lives in the crunchy, left-wing D.C. suburb of Takoma Park, threw a block party for his daughter’s bat mitzvah, got a master’s at Cambridge, and is the son of a chemistry professor and an English teacher — by all appearances a member of the liberal elite, not the oppressed proletariat. In fact, he has always worked for unions, rather than within them.

His route into the movement was more philosophical. Silvers grew up in poor, largely African American neighborhoods of Hartford, Philadelphia and Richmond — which his parents had chosen in order to live in an integrated community. “The idea that society was economically unfair was literally everywhere,” Silvers says.

The real organizing didn’t start until he arrived at Harvard for college, where on Wednesdays he washed dishes in the dining hall for extra cash. It was awkward, working alongside people whose life prospects were very different from his own. But when the dining hall workers’ union started agitating for a better contract, Silvers, who couldn’t join the union as a student employee, wore a button in solidarity.

“It was like, all of a sudden, everything was different,” Silvers says. “And the manager had a fit, because the students were the potential strikebreakers. If the students were not going to play ball, it was not going to work.”

The cafeteria workers won that campaign, and Silvers found new ones to wage: He helped lead the effort to get Harvard to divest its gigantic endowment from South Africa in protest of its apartheid government. After graduating and getting his master’s degree in 1987, Silvers returned to take a job with the 3,400-strong Harvard Clerical and Technical Workers, helping win a hard-fought election. But the glow of triumph wouldn’t last long.

In the early 1990s, while fighting plant closings around the country, Silvers remembers trying to run an organizing drive at a medical device company in upstate New York in midwinter. He visited an employee who told him she had been a shop steward at General Electric years before.

“I said to her, ‘That’s great, your coworkers really need someone with your experience and your leadership qualities.’ And she said to me, ‘Don’t you understand? We lost. We lost. I’m not doing that again.’ ”

Silvers didn’t like losing. And at that point, he realized that the problems facing the labor movement needed some more specialized knowledge. So he went back to Harvard for a joint law and business degree. In school, he would take trips to visit his future wife, Elissa McBride, also a union organizer, whom he’d met at a study group on finance hosted by a mutual friend in Washington’s Mount Pleasant neighborhood. He then clerked for a couple years in the Delaware Chancery Court, which deals with the world’s biggest corporations. In 1997, AFL-CIO officials hired him, taking notice of his ability to communicate just as well with Wall Street titans as he could with factory workers.

That’s one of Silvers’s habits: Inserting the experience of working people into D.C. talkfests where policy can seem totally divorced from its real-world effects. At a recent think-tank gathering of eminent European economists, Silvers disrupted the congenial discussion with a sharp dissent, analogizing the situation of struggling economies in Europe to that of the U.S. homeowner during the housing crisis.

“All kinds of nonsense and terrible stuff can be said as long as it’s said abstractly,” he said later, walking back to the office. “You string together enough abstract nouns, you can literally justify a massacre.”

In his early years at the AFL-CIO, he helped fight to get laid-off Enron and WorldCom workers fair severance packages after the scandal-plagued companies collapsed. Later, Warren — who had worked with him on bankruptcy issues back in the 1990s, calling him “very smart and very effective” — credited him with birthing her brainchild, the Consumer Financial Protection Bureau.

Silvers also gained the respect of people on the other side of the financial spectrum.

“I think tonally, he has shaped people’s thinking,” says Rodgin Cohen, the super-lawyer senior chairman at Sullivan & Cromwell, who represented several financial institutions during the crisis. “You can disagree with him, but he engages in rational argument as opposed to demonizing.”

Silvers is certainly difficult to demonize — colleagues call him an absent-minded professor, forgetting his wallet if he goes out, getting engrossed in side conversations that make him late to his next appointment as staff members exasperatedly try to keep him on schedule. But within the building, he’s also looked to as the one who really understands the forces they’re dealing with. A typical day might include delivering a lecture to the digital strategy team on labor’s problems with the health-care law, advising someone at a think tank on what to write about economic issues in China, and convening a lunch discussion of union pension fund managers. A proposal that pushes boundaries of what’s considered possible is known as “Damonesque.”

Behind it all, one basic conviction drives Silvers, and therefore the AFL-CIO: Unions don’t have a chance without a well-functioning market, in which capital is channeled toward parts of the economy that keep jobs in the United States.

That’s why the past four years of crises, standoffs and half-measures have been so distressing to Silvers.

In 2008, he was appointed to the congressional oversight panel charged with reporting on the administration’s $700 billion Troubled Assets Relief Program. Along with its chair, Warren, Silvers pounded Treasury officials over the course of more than a dozen hearings to do more for struggling homeowners and to discipline the banks.

“We are faced with a choice here,” Silvers said during one congressional hearing. “We can either have a rational resolution to the foreclosure crisis or we can preserve the capital structure of the banks. We can’t do both.”

Instead, the banks were merely stabilized. Silvers traces the political and economic dysfunction of the ensuing years — the lingering foreclosure crisis, anemic consumer demand and the rise of the tea party — to that one failure, along with the fiscal austerity that followed.

“They got exactly what we feared, except it was actually worse,” Silvers says, with a cold, barely constrained anger. “If I’d known what the consequences of the decision not to restructure the banks would be, I would’ve set myself on fire on the Mall.”

Give the labor movement credit for one thing: It recognizes it’s in deep trouble.

First of all, America’s future business leaders never plan to deal with unions. “Most have no knowledge, no interest, and no expectation of ever dealing with a labor leader,” says Thomas Kochan, an industrial relations professor at MIT’s Sloan School of Business. He helped bring Silvers into a project with Harvard Business School, which used to have more of a labor presence and now has almost none at all.

Another problem? The people who advise President Obama — whom the AFL-CIO fought hard to elect and reelect — don’t care much about unions as an institution.

“There are not many people around the president who are intuitively sympathetic to unions. That is a fact,” says a labor leader who has worked with Silvers and asked for anonymity to speak frankly about former associates. “There are people who would swear they’re left wing, but don’t see labor as a force in the grand left coalition.”

The disregard was painfully evident at a recent conference in Washington put on by the Commerce Department to lure foreign companies to invest in the United States. Panel discussions were stacked with titans of industry and finance. State economic development agencies set up displays in the exhibition hall, prominently advertising their right-to-work laws. Administration officials warmly introduced Wal-Mart executives at a news conference announcing that it would bring some of its manufacturing to the United States, creating jobs that pay about $10 an hour.

Organized labor wasn’t represented, despite its strong interest in the issue, and Silvers found the whole affair exasperating.

And the labor movement is faced with a more uncomfortable reality: Even if workers — say, for example, people in Amazon warehouses, fast-food restaurants, factories owned by foreign auto companies — do want more from employers, unions aren’t necessarily the first place they’d turn to get it. The AFL-CIO and its members are often still seen as special interests bound to an economy that doesn’t exist anymore, holding on to expensive pension programs that bankrupt cities, pushing for environmentally destructive but job-creating projects.

The federation took one big step toward attempting to change that perception with a convention in October, which prominently featured representatives of feminist and environmental groups, and welcomed unconventional not-quite-unions like the OUR Walmart campaign.

“We as a labor movement need to be welcoming of working people, no matter in what form they show up,” Silvers says.

Here’s another thing about Silvers: He likes to gamble, playing small-stakes blackjack at conferences near casinos, or at home with friends. Running the policy shop for the labor movement right now is kind of like that. When you’ve got a terrible hand, any bet is worth the risk.