West Winging It: My unforgettable time in the White House

by Pat Cunnane

Is it more like The West Wing or House of Cards? Do you have to put your try table up on Air Force One? Is the President any good at basketball? What do you call him when you talk to him? How do you pick the people the president meets with? Is he really that cool, or is it an act?

West Winging It pulls the drapes back on life in the White House, offering an insider's glimpse of what it's really like - from the minutiae to the momentous - to work at 1600 Pennsylvania Avenue. This brilliant book provides a front-row seat to history as, for the first time, Millenials ran the country - a classic fish-out-of-the-water story, only these fish are trying to run the United States of America.

With cameos from Barack Obama, Joe Biden and a colourful collection of characters in the form of staffers, Secret Service agents and slippery journalists - West Winging It is a truly unique take on one of the most unique offices in the world.

Genres: Nonfiction, Politics, Memoir, Biography Memoir, Humor, Biography, Audiobook

320 pages, Kindle Edition

First published April 17, 2018

About the author

Pat Cunnane was President Barack Obama’s Senior Writer and Deputy Director of Messaging at the White House where he worked for six years in many roles, responsible for everything from traveling with the President across the country and around the world on Air Force One to writing statements, jokes, op-eds, and more in the president’s voice. Pat did nearly 100 domestic trips and traveled to nearly 20 countries with the President. He worked on the president’s appearance on “Comedians in Cars Getting Coffee” with Jerry Seinfeld, which broke the series’ viewership records and helped garner an Emmy nomination. Pat lives in Los Angeles with his wife, Stephanie, whom he met in second grade. He now works as a writer on the TV series Designated Survivor, starring Kiefer Sutherland. Pat’s upcoming book, WEST WINGING IT: AN UNPRESIDENTIAL MEMOIR, will be out April 17, published by Simon & Schuster/Gallery Books. He has written for the New Yorker and Politico Magazine and is currently developing WEST WINGING IT for television with the Mark Gordon Company and working on feature projects. He likes golf and loves Sinbad.

Reviews

[Ml Lalonde · Rating 3 out of 5]

There is a new genre of memoir to make us even more sentimental for those heady days of stable government and moral leadership. It would seem that every man, woman and child in Obama's White House, traumatized as they were from the election of Trump, has written a book about the "changey hopey" years. Pat Cunnane makes the latest contribution. Cunnane is the most junior of staff members - the intern to the under secretary of the under secretary so to speak. He once sat down the hall and round the corner from the corridors of power. He played a game of golf with Obama. He answered the mail. He proposed to his bride in the rose garden. He did lots of stuff and people laughed and they went on trips and it was fun. There's nothing particularly cerebral or riveting about this book, although Pat seems likeable in a kid brother kind of way, but you'll finish this book reminded once again that the world was more innocent less than 18 months ago and we had Camelot again and we lost it.

[Susan · Rating 5 out of 5]

This book was excellent. It’s funny but also moving. I like how he talked about the minutiae of the job as well as the big events. The epilogue made me cry. It’s also a very sobering read comparing then to now.

I was provided a copy of this book by the publisher via NetGalley.

[Emily Louwsma · Rating 2 out of 5]

According to GoodReads, 2 stars = "it was okay". And this was very okay.

I had a lot of thoughts reading this. Since Pat himself describes good writing as "the intersection between strong writing skills, experience, expertise, and humanity", I'll use those areas to explore some of my many thoughts.

Strong writing skills... I struggled with some of the stream-of-consciousness that Pat uses throughout the book. He'll start a chapter talking about Jerry Seinfeld coming to the White House. The chapter starts with that idea, then travels through Sinbad (who the reader is inexplicably supposed to already know that Pat loves), WHCD jokes, Between Two Ferns, Mista Madd Hatta Show (with a joke about the CBO report that nobody outside of the White House is going to get), Obama going to Chipotle, reading mean tweets, memes, going to Camp David to shoot guns, more about Jerry Seinfeld, calling moms on Mother's Day, then finally back to Jerry Seinfeld again. That is A LOT for a chapter, and the way it was constantly broken up was just a struggle. It wasn't chronological and it was very tenuously linked thematically.

Experience... I'm using this to describe his life experiences. I naturally compare this book to some of the other books I've read about the White House before. From the Corner of the Oval and Who Thought This Was a Good Idea?: And Other Questions You Should Have Answers to When You Work in the White House are two that come to mind. Both authors have robust interests, personalities, and lives outside of the White House that they include in their book. I felt no personal connection to Pat because this book made him seem like he has ZERO personality. Here's what I know about him: he dated the same girl since 2nd grade, he went to U of Miami (... we were there at the same time), and he went on Semester at Sea. That's it! He talks about Semester at Sea so many times during the book that it just amplifies this lack of lived experience.

Expertise... In this case, Pat's expertise of the White House was actually a hindrance to his reader. He wrote so many times about things that *regular people do not get*. I struggled the whole time really understanding what he was saying and why. This book just seemed hastily written and didn't include a lot of information that would've been helpful. Throughout the book, I found myself constantly reading the White House wikipedia page to understand the layout of Upper and Lower Press and reading an organizational chart within the White House to understand who everybody was and what their role is. I totally get why Dan Pfeiffer would give this book a glowing review (personal connection aside), since many of the jokes seemed like "you had to be there", or at the least, "you had to have been there at least once to get the context" kind of jokes.

Humanity... Pat admits to getting roasted a lot. What he doesn't admit is how much of it seems completely warranted. When a privileged white man/son of a state senator and a business owner who sponsors a Tour de France team, is being self deprecating, it comes off really, really poorly. His personality just grated. Like when he'd say things like, he hates hearing about other peoples' dreams, then proceeds to explain his own dreams to the reader. So much of his self-deprecation came off as haughty.

Read instead:
Who Thought This Was a Good Idea?: And Other Questions You Should Have Answers to When You Work in the White House
Chasing Hillary: Ten Years, Two Presidential Campaigns, and One Intact Glass Ceiling
Who Thought This Was a Good Idea?: And Other Questions You Should Have Answers to When You Work in the White House
Yes We (Still) Can: Politics in the Age of Obama, Twitter, and Trump

[Beth · Rating 4 out of 5]

Another memoir by one of the "Obama People." And it's a very good one.

There is a lot of humor here but the author also understands the significance and gravity of working in the White House for a transformative president. His interactions with President Obama are a joy to read.

He touches briefly on the 2016 election results (he mentions ugly-crying in the Oval Office on the day after the election) but mainly focuses on his time in the White House as part of the Obama administration. I loved this description of the workforce there:

"Diversity in our workplace never seemed forced. It felt organic, like the pool of talent drawn to President Obama came from every background imaginable. Our differences were our strength..."

I still believe this.

[Dani Kass · Rating 2 out of 5]

Of all the Obama White House memoirs, I picked the one by the unknown, barely-experienced white dude for one reason: it was guaranteed to be FULL of West Wing references. I mean, it's called West Winging It. I was severely disappointed. The show was mentioned twice, and both in extremely offhand ways. It was pure false advertising and I'm pissed. It didn't hold up on its own merit either.

Pat Cunnane was some small guy in the press office, who, based on his own account, was an incompetent tool. He regularly made off-color jokes and bragged about how his coworkers kept a tally of when he crossed the line. He casually threw in lines like "I was pleased that my intern's Sinbad book report had now been supplanted as the least productive use of a White House intern's time since the Clinton years," talked about sitting Indian style and made fun of people with disabilities. He would admit that he was out of line often, but he embraced it as a character flaw that he couldn't control rather than actually doing something about it. It was about as typical of a privileged white bro tale as you could imagine.

The story is told in a nonsensical order, and it's all about him — even though almost no one knows who he is and even fewer people care. There was very little insight into the presidency and the few tidbits that could have been interesting were quickly summarized and dismissed. He did provide an okay-enough view of the inner workings of the press office, which appealed to the journalist in me.

Cunnane's writing was subpar. It was often repetitive or awkward or just flat-out bad, which is only worth mentioning because he goes on a long rant about how gifted of a writer he is.

Overall, I feel pretty comfortable saying this book was a complete waste of time. At least it was a fast read.

[Pamela · Rating 5 out of 5]

Reading books like this reminds me that it wasn't that long ago when the WH was truly the people's house filled with competent, smart, caring people who were honored to work there. Jay Carney, former press secretary describes this book best..."a fun, poignant reminder that the best part about working in the Obama White House was the people working with you and knowing that everyone was there for the right reason: to try to do as much good, for as many people, as we possibly could."
Reading this helps me keep focused on moving forward and gives me hope that someday we will return to stability and dignity. I didn't know that Cunnane now writes for Designated Survivor!

[Beth · Rating 5 out of 5]

I loved reading this. I loved hearing about President Obama who said: "Every moment we are in office here, we are in service of the American people". A man of such intelligence and integrity and I really miss that. He cared so much about all the people. I hope that we have that kind of president again in the future.

[Kat]

Definitely the least interesting of all of the Post Obama Administration books by his staff. Save your $ and just buy Alyssa Mastromonaco or David Litt’s books. Those books are actually funny, engaging, and worth your time.

[Landers · Rating 4 out of 5]

Wow, I miss the Obama presidency years. This was a good book - I read it in one sitting - that gave insight into working for Obama and the very cool, pinch yourself moments... and it also include so many reminders that it was also just a normal workplace, which I particularly loved. This book was funny and endearing and at the end of the day, it made me smile.

[Chris Johnson · Rating 4 out of 5]

For those interested in learning about working in the White House, look no further than this book. It showcases the tireless work staffers do to run the country.

[Wallace Hettle · Rating 4 out of 5]

A very good read, and a reminder that idealistic people can make government work.

[Paige Kilian · Rating 4 out of 5]

I am on a roll with memoirs. Thoroughly enjoyed this one, too. Probably a 3.8 :-)

[Kay Cugini · Rating 5 out of 5]

Great read, very entertaining and interesting, good humour, really enjoyed this one

[Patrick · Rating 4 out of 5]

4.5 - These are the kind of White House stories I crave. Not from people working in the POTUS cabinet or extreme inner circle, but from the “regular” workers. I was desperate for something that reminded me of The West Wing and this scratched that itch.

[Allison Rowland · Rating 4 out of 5]

Maybe more like 3.5 stars. If you’re missing Obama, this is a nice insider’s walk down memory lane.

[Claudine · Rating 2 out of 5]

Listening to this book on Audible. Maybe I should have read it. Or maybe Pat Cunnane should have hired someone to read it. The parts that should be funny, aren't. Or maybe they just aren't funny period. So far, the other Obama Era memoirs put this one to shame.

[Laura · Rating 4 out of 5]

Great read for those of us in the “I miss Obama” club...

[Meg Boucher · Rating 5 out of 5]

'West Winging It' not only gives you an inside look at the day-to-day workings of the White House, but also highlights the camaraderie and decorum that were synonymous with the Obama administration. The book allows you to experience the West Wing through the eyes of a staffer. Plus, Pat's sense of humor, interjected throughout the narrative, will make you laugh out loud.

[Michael · Rating 4 out of 5]

Breezy, light-hearted look back at a "simpler" time. It was nice to look back at what the upper levels of government looks like normally from someone that started out as an intern. A welcome, quick distraction that was worth the read.

[Anya Leonard · Rating 5 out of 5]

A hopeful look back at the Obama White House from someone who lived it. Pat Cunnane is adept at sketching a very good outline of what it was like behind the scenes in the press room during the Obama administration. Those of us who voted for him will be happy to see the glimpses behind the calm and collected exterior that he wore, and see that he was just another person, doing the best he could in a difficult situation.
This book is very well written, obviously Mr. Cunnane is well-educated seeing as he was taken on as an Intern at the White House at the age of 22, and was hired on as a full-time employee. Seeing how the residence operated at a time when normality was the order of the day is refreshing when we have the unknown upon us constantly with this new administration. It’s nice to remember a president who respected the media to some extent and allowed equal opportunity to both left leaning and right leaning organizations.
Read this book if you would like to reminisce and if you need a little bit of fire under your butt for the 2018 elections!
This book was provided by NetGalley in exchange for an honest review.

[Zandria Senft · Rating 4 out of 5]

A very honest, touching memoir about Pat’s experience working at the White House during the Obama Administration. I can say I am not one involved in politics but I very much enjoyed learning Pat’s story!

[Max Godin · Rating 3 out of 5]

Maybe I'm being unfair, having read two Obama, 'my time at the white house,' staffer books, one after the other but this definitely came off as the weaker of the two. It was fun and interesting to hear about his time working for President Obama but often what he brings up, it lacks meaning or any genuine depth.

In comparison to the memoir written by David Litt, Litt was able to weave his own personal experiences together with the bigger moments of the Obama presidency, Cunnane fails to this here and that is what is lacking.

Moreover the writing style does take a lot of getting used to and I cannot confess myself to being a fan, he jumps around a hell of a lot. For example, he'll start talking about one subject but before he finishes subject one, he goes through subject two, three and four, then back to finishing one. I felt like Cunnane wrote this because he could, not because he had anything insightful to share

[Ann · Rating 4 out of 5]

I enjoyed reading this book about the staff and behind the scenes look at the White House during the Obama years. Pat Cunnane has a writing style that is easy to read and injects humor into many of his chapters. He gives a glimpse of the presidency that is not often covered by the press and how various team members help shape decisions and ideas. I'm sure there will be numerous books on politics dwelling on this time frame but this one had a more human viewpoint into a jaded political arena.

[Fiona · Rating 2 out of 5]

I had to give up with this book.

It should be an enjoyable light read, and I can see the attempt, but the truth is that Cunnane's writing is just flat and uninspiring.

There is nothing to particularly dislike, there's just not a lot to like. Most of the humourous little snippets were probably more 'you had to be there' moments, and even those with more obvious comedy value, or the details of the White House and it's day-to-day running, just fall flat in Cunnane's hands.

Some interesting content, made tedious.

[Frank Brennan · Rating 2 out of 5]

Very disappointing. Pat spends entire too much time on the staff and press corps. With the exception of the insight he provides on the White House itself, you don't really get a good look at Obama or any of the key players during the years he was there. Nice try. But it just doesn't work.

[Lauren Taylor · Rating 5 out of 5]

Amazing first hand account of some of the most memorable moments from the Obama presidency. Great political pick-me-up to read.

[Sarah Ewald · Rating 5 out of 5]

Oh, how I miss the days when we had a president that spoke in measured tones, and knew how to say things that inspired us. A president for whom America's story was his story. So unlike our current president, who opens mouth, and nonsense emerges, 'stream of unconsciousness' thoughts spill out.
Pat Cunnane worked, first, in a low level job of media monitor; i.e. watching the news, pulling clips on the administration, scanning newspapers, web sites, etc. Pretty boring, but in the Obama administration, as of those that went before, necessary. He worked is way up to the communications department, and later in his employment, to occasionally composing press items, and words that President Obama was to speak.
He came into the job not knowing what POTUS stood for, and left traveling with the president, writing statements that reflected the president's voice.
This was an enjoyable behind the scenes look at the Obama White House, good and bad, funny and serious. Every president has an unenviable event in their administration when called upon to unify the country and console the un-consolable. For Clinton, it was Oklahoma City, Bush, it was 9/11.
For Obama it was December 14,2012 and the Newtown/Sandy Hook shootings. Called on to honor the victims with the call to action, he became a 'consoler in chief', only to have to assume that role multiple times in Orlando, and after the Emanuel African Methodist Episcopal Church racist attack in Charleston, S. Carolina. I am brought to tears as I remember him eulogizing the victims and starting to lead the mourners in singing 'Amazing Grace.' (cannot even imagine our current president do so.)
Tasked with finding Americans for whom measures Obama enacted changed their lives, he found Brent Nathan Brown writing to the president. This gentleman acknowledged that he didn't support Obama and was a staunch Republican. Yet he felt compelled to write to the president thanking him for enacting the Affordable Care Act, saying he saved his life. Due to pre-existing conditions for which he was unable to purchase insurance, the ACA stepped up to give him access to the insurance and care he needed. Pat says his favorite moments include ones when he makes a call to a letter-writer, and saying, "I'm Pat Cunnane and I am calling from the White House in Washington, DC."

The Obama years, I realize, are years that some people hold in contempt. I find, however, an inspiration in those years. Something that is missing today.

[Joseph J. · Rating 5 out of 5]

Won in a Goodreads Giveaway, and very appreciated. Twice I voted for Barack Obama, but there is an inherent message for all in these recollections of a young White House staffer who rose from entry level job to a major role in the White House Press office of President Obama. The message is valuable and poignant in light of current events. Pat Cunnane writes that while the Obama press office often was at odds with the working press in the briefing room, they always recognized that those members of the press had the best interest of the country in mind. Obama staffers may have resented and angrily noted what they perceived as inaccuracies and unfairness in reporting, but the reporters were never seen as enemies of the country. Overall, a spirit of, well fun, pervades these recollections of a young guy just out of college, in no way a part of the 08 Obama campaign, who through talent and pluck rises, or crosses West Executive Avenue, to a post in the everyday workings of the press office. There is an idealism and a joy in his memories which I would guess is lacking in the present press office. The opposition is not always the enemy, and cannot be labeled with the blanket indictment of hatred of America simply by opposing an administration. The quick wit of Press Secretary Josh Ernest is very much missing today. There is much warmth and humor in these memories of Pat Cunnane. His humility is evident in those moments when he had to pinch himself as he witnessed history (the second "private" inauguration), and those humanly awkward encounters we can all appreciate, i.e. his first encounter with Joe Biden. Indeed, he quotes the former veep's late mom: "They're no better than us, an we're no better than them." Words appropriate for inscription in the White House Press Briefing Room, and yes the Oval Office of all Presidents.

[Edmund Vale · Rating 4 out of 5]

West Winging It struck me as a book born of curiosity and good humour, written by someone who doesn’t take life too seriously yet pays close attention to the world. It’s less about polished insight and more about honest observation. the kind that comes from spending time with people, places, and stories without the need for grand conclusions.
What stayed with me was Cunane’s friendly tone. There’s a lightness here, but it isn’t careless: it’s warm, self‑aware, and grounded in real experience. The book embraces its own imperfections, and that felt refreshing. Instead of announcing big lessons, it simply invites the reader to see alongside the author to notice quirks, contradictions, and the sometimes absurd texture of everyday life.
This isn’t a work that demands to be studied; it’s one that invites you to relax into it, smile at a dry observation, and perhaps recognise a truth about yourself in a casual aside. Reading it felt like sharing a conversation with someone who notices the world in a way that’s both curious and kindly.

[Christa Van · Rating 3 out of 5]

The inside scoop from a kid who started as an intern and worked his way up to a writer for President Obama. Pat Cunane has a wonderful ability to make fun of himself while appreciating every minute spent in the White House but never overselling his importance. I loved the "little stories" the best. Once Pat slammed a door in VP Biden's face and then apologized to his assistant. He hesitated to be in the frame of a picture taken of his fiance and the president, just in case their relationship didn't work out (he sweetly wanted HER to have a memory with the president). The attempt to get Pope Francis to bless him by sneezing in his presence is pure genius. Traveling with the president and wrangling the press sounds like a job only for the young and agile. Not a hard hitting political story, but very fun to read.