Dan Pfeiffer Lays It On The Line 

The Pod Save America host and former Obama communications director says Democrats must be disciplined and realistic to defeat the president.

click to enlarge Pfeiffer parlayed his Obama experience into a successful podcast.

Pfeiffer parlayed his Obama experience into a successful podcast.

Podcaster Dan Pfeiffer says people hoping to dump Trump in the 2020 presidential election must be tough, work hard, use realism and act as idealists without delusions.

The best-selling author, former White House communications director during Barak Obama's presidency, and co-host of Pod Save America appeared December 5 in conversation with Inflection Point radio show host Lauren Schiller at Zellerbach Playhouse. Presented in Cal Performances' seven-event speaker series consisting of leading thinkers, activists, and commentators on politics and contemporary culture, Pfeiffer was greeted by an enthusiastic audience of roughly 250 people.

Although clearly preaching to a choir whose occasional applause and cheers demonstrated the majority had arrived having drunk the Kool-Aid of left-leaning liberalism, Pfeiffer's take on "un-Trumping America" avoided deep dives in partisanship. Instead, Pfeiffer demonstrated high-level candor while constructing a portrait of haphazard events that placed him at Obama's elbow, the role of traditional and social media in politics, weaknesses in the Democratic Party's messaging and candidates, the impeachment inquiry's significance, and activism necessary for Democrats to win back the White House.

Pfeiffer was born in Delaware, grew up talking about politics, and had a mother who took him with her into the voting booth from an early age. After working on three (losing) presidential campaigns — for Al Gore, Tom Daschle and Evan Bayh — he decided to put off law school and do one more. Then-Illinois Senator Obama gave the keynote speech at the 2004 Democratic National Convention and learning Obama was hiring, Pfeiffer met with him and one hour later had accepted a job as campaign communication director, eventually rising to communications director in 2009 and senior advisor in 2013.

Asked by Schiller about his position and why he departed in 2015, Pfeiffer said his job was to interpret and communicate Obama's "wishes and desires" on everything from digital strategy to whether or not Obama would want to be consulted before an action was taken. When he told the president he was leaving because he was worn out from long hours and travel, Obama said he was also tired but wasn't leaving office. Pfeiffer told him, "Yeah, but you (live) above the office and have a bed on your plane; I don't."

As a 33-year-old when Obama was elected, Pfeiffer admits his biggest missteps were due to sometimes overcompensating feelings of inadequacy by "being overly aggressive and louder than was necessary." Obama, he said was always a calm, supportive boss.

Asked about presidential candidate and former Vice President Joe Biden, Pfeiffer praised his character and said Biden was legendary and omnipresent in their shared home state. "If you go to the grocery store ten times, you'll see him two times."

Addressing the greatest difference between 2008 and today in the electorate, Pfeiffer said, "People are afraid in ways they weren't in 2007." With fear as the primary driving emotion, a "win," he suggested, will come with a leader who unites the country, isn't romantic about Congress healing the rifts, and admits we still have a nation in which the rich have more power than poor people.

Exacerbating the divide, traditional news media is ultimately a hyperactive news delivery business that leads some people to think "well-coiffed investigative reporters who look like Robert Redford and Dustin Hoffman are going to take down the president." Social media exaggerates a non-serious, non-reliable news feed by having "no rules" about truth, mass confusion, and doubt due to millions of voices, and encouraging outrage. Overall, he believes, Democrats are outfoxed by Republicans and Trump — metaphorically and literally, with Fox News and conservative outlets delivering effective, pithy messages.

Democrats would be helped by communicating complicated ideas — on health care and climate change, in just two examples — with simpler language and debates on the merits of positions taken on topics important to voters. A "silver bullet slogan" isn't the answer, according to Pfeiffer. Instead, a compellingly told story appealing to core democratic voters and people who don't typically vote is, arguably, Pfeiffer's "suggested winning formula."

The 2020 Democratic candidate must also "do more than appeal to white men in Wisconsin." Asked by Schiller about the top candidates who, after Kamala Harris departed the race, Schiller described as "five white men and two white women," he said remembering recent history and the 2018 election outcome meant the party is best led by a person able to attract voters from communities of color and women.

Audience questions focused primarily on strategies for taking back the White House. The impeachment inquiry, even if it keeps Trump "tweeting chaos," won't make a big difference in the outcome of the election, according to Pfeiffer, whose new book, Un-Trumping America, will be published in February. Divisiveness within the party, one person suggested, might. "Debates are good but become damaging when they go to character," Pfeiffer agreed. "You believe this because you're a shill," he said is an example of a harmful, judgmental statement.

Ultimately, Pfeiffer predicted that creating unity, making a case for electability to defeat Trump, and inspiring a groundswell of activist citizens are essential for any Democrat hoping to win in 2020. "Voters are not idealogical; activists are," he said. "Voters want someone who will fight for them, someone they can trust. Electability is about the candidate's ability to tell a broadly appealing story."

And then the real work starts, he believes: eliminating the Electoral College, reducing the terms of justices on the Supreme Court, eradicating the U.S. Senate's filibuster, and addressing massive nationwide problems with homelessness through a multiagency effort are only the beginning. Like Pfeiffer said, winning is tough.

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