How the Message Got Made in Obama’s White House

Book review: West Winging It, by Pat Cunnane

This year and last have seen a wave of newly published memoirs from former Obama staffers. I read speechwriter David Litt’s wonderful, charming Thanks, Obama last year, so after that I was on board with the genre. West Winging It begins with a similar premise – young college grad Pat Cunnane stumbles into his first “real” job and it happens to be in one of, if not the most, pivotal presidencies of the modern era. He’s a bit clueless from the get-go (get the title?) and does a little fake-it-til-you-make-it. For him, “making it” was reaching the post of senior writer and director of messaging, which involved writing words to be attributed to Obama. Not bad.

But he begins as a lowly media monitor, which entails combing through and pulling relevant media stories with the intensity of a Kardashian monitoring their Google alerts and sending the links around to staff. It sounded exhausting and never-ending.

From there, he moved up in the media and communications department, becoming a press aide. This included wrangling duties of the White House press pool, which allowed him the enviable but hectic perk of traveling around the world with Obama. Cunnane’s responsibilities involved organizing the core White House press members and making sure they could (or sometimes purposely couldn’t) photograph the presidents at events, speeches, wherever he happened to be and whatever he was doing.

Eventually he was writing pieces and press releases to be released as Obama’s voice, often things like obituaries – requiring both sensitivity to the subject as well as consideration of the presidential voice. This sounded like such fascinating work, and when we get glimpses of Cunnane doing that work, the book is at its best.

It’s intended to be humorous, and although the tone and reliance on footnote humor didn’t always work for me, it did have its hilarious moments. My favorite:

Occasionally, older journalists would meander up our tight hall – taking full advantage of the fact that none of us had doors – and recount what notable people had sat where and when. They particularly liked to remind [a colleague] that she was sitting in Diane Sawyer’s old seat, and that George Stephanopoulos was right here, and Rahm Emanuel over there.
“I heard John F. Kennedy used to work over there, too,” I wanted to say while pointing toward the Oval.

I really did lol.

An interesting and well done aspect is his careful highlighting of some differences between how the Obama communications staff worked and how the current administration’s floundering communications department…I don’t want to say works, because that’s generous, but “functions”, maybe. He burns them without even addressing them.

Josh [Earnest, former press secretary] liked to say that the briefing is a venue to make an argument. But that argument is fruitless without a set of facts from which to work.

But we knew something that we thought obvious; something we thought never needed to be said, but maybe it does.
The press is not the enemy of the American people.

With some clever commentary and intriguing behind-the-scenes glimpses, he shows how “the message got made” when Obama and his very young (I never realized how young) staff were running the show.

I didn’t like certain personal-memoir aspects of the book – inconsiderate as that might sound. I just liked hearing about his work, less so the personal stories. I was also more curious about his educational background and the logistics of getting to the White House as an intern originally, but that’s skimmed over with only an anecdote (amusing as it is) involving Larry King and Dr. Phil.

There’s also a thread running throughout, light-hearted and jocular though it is, that feels uncomfortable sometimes, regarding his being the butt of workplace jokes. It makes you feel sorry for him, because he comes across as well-meaning, and maybe some was even exaggerated, but I just didn’t always enjoy reading about it. There’s also a lot of the type of humor and characterization of coworkers that works in something like The Office because we have the extended medium of a show to get to know character quirks, but the short sketches here didn’t make enough of an impression to be that amusing. It feels like you had to be there.

He’s at his best while describing his work – the pitfalls, the places where it goes wrong, and even the minutiae of what his job entailed. I’m fascinated by other people’s jobs and he had an undeniably captivating one. For all of his joking and the bickering office politics that even the White House can’t escape, it’s clear that the experience was incredibly meaningful for him. I found it touching when he wrote that “It was the honor of my life” to write hundreds of pages of words that were attributed to President Obama. I bet it was.

The late White House press secretary Tony Snow once said that it’s the people on the outside looking in with the real perspective on the place. “They know what you’re likely to forget…Leave no room for regrets, for someday, in the not-so-distant future, you will be back where you started: on the sidewalk with the other folks, gawking at that grand, glorious, mysterious place where Lincoln walks at night; and our highest hopes and dreams reside.”
If only those passersby knew.

Mostly distracting, light look at a young staffer’s White House days. Verdict: 3/5

West Winging It: An Un-Presidential Memoir
by Pat Cunnane
published April 17, 2018 by Gallery, Threshold, Pocket Books

I received an advance copy courtesy of the publisher for unbiased review.

 Affiliate links included from Book Depositorya great site (I’ve bought there) offering free shipping, worldwide. I get a small percentage of the sale – you pay nothing extra – if you use my links to buy books seen here. I’m never paid to promote or review any title.

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