Obama Aide’s Book Blurs Lines Between Memoir, Comedy and Political Analysis

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Yes We (Still) Can: Politics in the Age of Obama, Twitter, and Trump
Dan Pfeiffer
Twelve Books

This November will mark the ten-year anniversary of Barack Obama’s election.  Though he has only been out of office for almost nineteen months and is a relatively young ex-president at the age of 57, most Democrats would probably say that Donald Trump’s presidency feels like Obama has been gone much longer.  Without a clear leader in the Democratic Party and a general feeling of goodwill and nostalgia for his presidency, former Obama aides and cabinet members have been gradually writing and publishing books with their own take on the 44th president.  The latest to do so is his former communications director Dan Pfeiffer.

Pfeiffer stays away from the traditional political memoir format in his tome, as opposed to works released by other Obama administration alumni like David Axelrod, Timothy Geithner, Leon Panetta or Ben Rhodes. Rather, his book melds a combination of a memoir of his life in politics, a personal post-mortem of the 2016 election, and an effort to make the connections in the political progression that led the American electorate to veer wildly from electing Barack Obama to electing Donald Trump.  Obviously, he does so through the prism of a Democratic political operative and with the benefit of hindsight almost 18 months after the presidential election.

The underlying thread connecting both Obama and Trump is the shifting media landscape due in no small part to the evolution of the Internet, social media, and means of communication, which both men excelled at, though Democrats would argue that Trump uses them for more nefarious purposes – his tweets, pushing conspiracy theories, and creating an information bubble that is difficult for independent outside sources to penetrate. (Pfeiffer describes Twitter as “a performance-enhancing drug for politics,” and compares it to using meth because of its addictive nature.)

Anyone who has listened to Pfeiffer on an episode of the Pod Save America podcast which he helped launch with three fellow Obama alums knows he can be foul-mouthed in his humor and political commentary, particularly when engaged in commentary with one of his co-hosts.  While reading the text, it’s easy to imagine hearing him saying these things during an episode of the show. Though he is an openly partisan Democrat, he is not a propagandist or an apologist in his writing or his commentary. He does critique mistakes and offers differences of opinion about Obama personally, the administration he served in, and the Democratic Party as a whole.

One of the more illuminating parts of the text is how Pfeiffer and the campaign coped with conspiracy theories about Obama as the years progressed. In the early days it was forwarded chain emails alleging he was a secret Muslim, later on it was the full-blown birtherism that Donald Trump used to launch his political career.  This culminates in Pfeiffer’s back story behind writing the jokes for the 2011 White House Correspondents’ Dinner during which Obama infamously roasted Trump, an episode that some have speculated was a factor in his decision to run for president and his personal animus toward Obama.

One of the most amusing episodes in the book which Pfeiffer dedicates an entire chapter to is the time he split his pants in the Oval Office, and his frantic attempts to fix them before being called again to accompany the president to a press conference. There is also the scary account of him nearly having a stroke because of the toll the long hours and stress was taking on him physically, caused by a combination of a blood vessel in his brain and high blood pressure.

Readers who study presidential history and are looking for a bombshell revelation or profound insight about the Obama presidency will be disappointed, and are better served by more traditional Washington insider memoirs or books by historians and journalists.  However, some of the most intriguing parts of the text are the ones Pfeiffer hints at but does not elaborate on.  This specifically refers to his many experiences with candidate and president Barack Obama over the years, in which rather than giving up the goods himself, he defers to his former boss to let him tell his own story in his own words, presumably his upcoming presidential memoir. (Michelle Obama’s memoir is scheduled for a November release after the midterm elections.)

Even the stories he does tell about his personal memories of Obama shed some personal light on the former president: how Obama told him he was running for president, behind the scenes decision-making on the campaign and in the White House, relationship and marriage advice, Obama’s reaction to a long-winded question from Kanye West during an A-list fundraiser, and a rare example of Obama losing his temper when he walked into the White House communications office and delivered what Pfeiffer describes as “a twenty-minute, not entirely family-friendly rant about the opposition party.” This is the kind of story that probably would have leaked instantly in the Trump White House, but managed to remain secret until well after Obama left office.

Until Obama’s book is published, we are left to speculate about what other stories Pfeiffer might be alluding to. However, because of the timing, it is also worth noting the dramatically different reaction Pfeiffer’s book got compared to the critical and political reaction to memoirs by Trump administration alumni Sean Spicer and Omarosa Manigault-Newman.  (For historical context, the only memoir really critical of the 44th president written by a former Obama cabinet official so far was Secretary of Defense Robert Gates, but even he didn’t take the burning down the house approach to it that Manigault-Newman did. It’s inconceivable to imagine an aide in any other administration surreptitiously record private conversations inside the White House Situation Room or a phone call with the President of the United States and release at least some of those recordings.)

One thing worth noting: Pfeiffer buried a lot of his jokes in the footnotes at the bottom of the page throughout the text.  This gives the book a feel – intentionally or not – of Pfeiffer breaking the fourth wall like Zack Morris or Frank Underwood.

Is Pfeiffer’s tome Obama nostalgia? No, though most Democrats say they miss him every day. It’s a different take and a different style from the usual Washington insider memoir, arguably for the better. Pfeiffer had a unique vantage point to witness the Obama presidency, but he wisely tells the story in his own voice, rather than make it into a more scholarly text. Perhaps most importantly, what Pfeiffer does in his book is an honest attempt at answering the basic question that has bedeviled the country since Election Night 2016: how did we get here?

Author: David de Sola

Editor/Publisher Political Wilderness

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