PHILADELPHIA — Nancy Pelosi knows a little something about being the only woman at the top of an org chart, and a whole lot about dealing with an opposition intent on portraying her as a Dragon Lady in a pantsuit.

In the 240 years of the republic, no woman has risen higher than the former House speaker (she’s currently Democratic leader) and there’s really no politician in America who can better understand Clinton’s attempt to scale the heights, her struggle to combat image problems and the sui generis challenges of competing in the ultimate hostile workplace, national politics.


Pelosi and her party’s nominee aren’t especially close (the Clintons suspected Pelosi of quietly backing Barack Obama in 2008, despite her stated neutrality) but the two now have a foxhole-buddy mutual respect, and fewer surrogates have been as aggressive on Clinton’s behalf (after Pelosi finally endorsed her before the decisive California primary on June 7).

And she had some advice for Clinton, given during a somewhat rushed half-hour sit-down for POLITICO’s “Off Message” podcast, counsel based on her own experience culled from a decade of vilification at the hands of the GOP.

“I think she is going to build confidence,” said Pelosi, sitting in Google’s box two levels above the floor of the Wells Fargo Arena a few hours before the, ahem, lively convention commenced on Monday. “Her numbers will improve, but sincerity — what do they say? Sincerity is the most important thing in acting. Once you can fake that, you've got it made. Trump has faked that very well.”

Pelosi added, with a pause to get the delicate phrasing just right. “She truly is sincere, but she has to connect more with the American people in terms of what she believes in and how she intends to accomplish progress in their lives,” added Pelosi, the daughter and sister of Baltimore mayors, and a feared political warrior known for her mastery of the inside game.

When I ask whether she agreed with Clinton’s assessment that female candidates are subjected to a double standard (a sentiment echoed by President Barack Obama in our January podcast), the former speaker shook her head in the negative.

“I think that Donald Trump is being treated to a premium standard,” she said, amending Clinton’s assertion. “Why predicate everything else on what-do-you-think-about-what-Donald Trump said? Who cares? Donald Trump is a here today, gone tomorrow presidential candidate.”

Pelosi, for two decades a pillar of the Democratic Party establishment, had her own bitter experience participating in left-wing presidential insurgencies. “Jerry Brown, I was his delegate in ’76 — we thought we were going to win over Jimmy Carter,” she recalled. “In ’80, Kennedy thought he was going to win ... In ’84, Gary Hart had one of the biggest shows of delegates’ enthusiasm — when Mondale had the nomination. So, this is not an unusual thing. We shouldn’t make a big thing of it. But at some point, it’s a bandwagon, it’s leaving the station. We have to go. And some people just want to convoy and we’re not going as slow as the slowest ship.”

From the moment she took the gavel in early 2007 to the instant she handed it over to Republican John Boehner in 2011, the 76-year-old Bay Area congresswoman was a magnet for attacks. The core GOP strategy for her four-year-tenure was to portray her as the embodiment of elitist San Francisco excess in 1-inch heels. She estimates Republican committees and their allies spent north of $100 million just to demonize her.

Pelosi doesn’t want to say any of that had to do with sexism, but she really thinks it did — and still does, friends and allies have told me over the years.

But evading the question, to some extent, is the point: When you get to the rarefied level she and Clinton inhabit, you’ve got to invent a new lexicon for discussing gender in politics — much as Obama tried to do with race in his presidential campaigns. You need to talk about it without quite talking about it.

“I don’t think that any woman should be asked to vote for someone because she’s a woman, and that — because the candidate is a woman,” Pelosi said.

“When I was running for leadership, the last thing I would say to my whips [was], ‘Do not ever say to anybody it's time for us to have a woman in the leadership,’ because that’s the least important selling point,” she said, going on to offer some unsolicited advice: “In terms of Hillary Clinton and this election, I think that the attitude that … you should vote for her because she’s a woman and you’re a woman is not a good selling point. And I think that turns some people off.”

But then, when I asked her explicitly what advice she would give Clinton, Pelosi shot back: “Be yourself … Don't worry about those other people. That’s their problem. They have an anti-woman attitude, that’s their problem; that’s not yours.”

Pelosi grew up around Democrats, and she has a kitchen-table comfort striding around the convention; she seemed more interested in showing her two young grandsons a good time than in making any huge political points, and when our discussion was interrupted by a blaring hip-hop music sound check, she walked over to the precipice of the box and began cha-cha-ing to the beat almost unconsciously. Pelosi was hearing the distant chords of her own childhood, when the convention really was one big party.

When I brought up the turbulence of the DNC email scandal and the Bernie-or-bust backlash against Clinton, she rolled her eyes.

Pelosi attended the 1968 convention in Chicago as a young mother pregnant with her second child, shuffling from the strife-wracked convention floor to Grant Park — where she watched in horror as the anti-Vietnam protests she supported were crushed by Mayor Daley’s truncheon-swinging cops. “This?” she said, before we turned on the recorder. “This is nothing compared to that.”

Yet a version of the same generational conflict playing out here was prefigured there: Her father, the legendary Baltimore mayor and congressman Thomas D’Alesandro, and her brother Tommy — the city’s future mayor — battled bitterly in the Maryland delegation over the future of the fractured party. The father enthusiastically backed establishment liberal Hubert Humphrey; the son, a fervent supporter of slain Bobby Kennedy, held out.

Pelosi sees few parallels between then and now, but she made a point of recalling the consequences of failing to fall in behind a flawed-but-sturdy nominee, and the perils of a progressive leader refusing to fully commit to the cause. “I thought that — and this will offend some — that Gene McCarthy could have done more to bring people together because the election of Richard Nixon was a terrible thing for our country,” she said, shortly before Bernie Sanders delivered a podium-pounding summons to his backers to vote for Clinton.

On Monday afternoon — as Democratic staffers and media fixers scurried around like hive-ants — Pelosi glided through the venue with a placid smile, like a grown-up daughter touring a comfortable if careworn childhood home.

“I went as a little girl with my parents in 1952 and 1960,” she recalled as an aide took her grandsons away to see the floor, where all those balloons will drop on Thursday. “At the ’52 convention, I was a little girl, and so my parents got me this big donkey — a stuffed donkey.”

Her father, then a dapper former city councilman with a pencil moustache, told her, “We’re going to name it for the nominee.”

The problem, then as now, is that all the names were acceptable but not ideal.

“Adlai, Averell, Estes, these were names that we didn’t have in Little Italy in Baltimore,” she said, referring to Stevenson, Harriman and Kefauver.

“The donkey ended up being Adlai,” she added.

Stevenson lost to Dwight Eisenhower.

