First Published September 2018
WEST WINGING IT
Senior Writer & Deputy Director of Messaging on Life In and After the Obama White House
Imagine… coming out of college at just twenty-two years old and your first ‘real’ job in the ‘real’ world being in the White House. Yes, THAT White House. The one with what is perhaps the most famous address in the world; 1600 Pennsylvania Avenue NW, Washington, D.C., 20500. And imagine that the man sitting in the Oval Office during your time there carried daily upon his shoulders – with the most inspirational and genuine displays of personal dignity and sense of public service and responsibility – the weight of being the first African-American to lead the free world. And imagine being right at the heart of the American political machine for six intense years, watching your boss, your nation’s President, reviled, mocked, and purposely hindered at every opportunity by the opposition, while at the same time being adored and respected by supporters of your own party and most of the rest of the world.
Then, imagine being there, in the midst of the maelstrom, as the seemingly impossible happens and you found yourself facing the reality of witnessing an individual who was, and remains, the polar opposite of everything great and good that had gone before, becoming the new President of the United States.
For one thing, this would make a heck of a movie! But fascinatingly, for one man, this was his life. That man is Pat Cunnane. He became Senior Writer & Deputy Director of Messaging in the White House. And his President was Barack Obama.
Pat served in the West Wing of the White House in President Obama’s administration, working as a media-monitor, press-wrangler, and writer between 2010 and 2016, or to give him his official title, as mentioned above, Senior Writer & Deputy Director of Messaging. And thanks to his magnificent memoir of that time, ‘West Winging It’, we don’t have to imagine what it would have been like to be there. We can hear it, from the heart, from a man who was. I had the pleasure and the privilege of chatting to Pat not so long ago. If you have even a passing interest in politics, history, the challenges of the times we live in, and the intricacies of human behavior in one of the most all-consuming workplaces on the planet, you’ll love this book, and I can’t recommend it highly enough. You’ll also laugh more than you’d ever expect to when reading a book that covers six years of a life in politics. And that says everything about Pat, and indeed, the many amazing characters who he shared his journey with, not least of all President Obama himself.
Pat, first of all, thanks a million for taking the time to have this chat today, I really appreciate it. So listen, the main reason you and I are talking is because you’ve just released your book, ‘West Winging It’, about your time as a member of staff in the West Wing of the White House during President Obama’s administration. I have to say I loved your book, and if it wasn’t for the need to sleep, eat, and work, I would have finished it in one sitting! So congratulations on creating what is really a very personal, and very human document of a special time in your life, and of course, a momentous time in American life too, for so many different reasons.
“Thank you so much, that is wonderful to hear!”
Let’s start with the actual process of putting your book together.
Was that something that you enjoyed? And with there being so many ways that you could have approached it, and with so many stories that I’m sure you could have told, was it tough to find the exact road you wanted to go down, and then to keep on that road as well?
“For the most part, I enjoyed the process. In the beginning, my notions of what the book could and should be were quite vague, but something clicked the day after the election in 2016 when Trump won. I knew then what I wanted the book to be: a time capsule of an administration that just ended – that now feels like ages ago. And a look at what it used to mean – and what it can mean again – to work at 1600 Pennsylvania Avenue. I kept mostly to the road-map I laid out from the start, but definitely allowed for some adjustments and plenty of feedback, which I think made the book better.”
So many ex-staffers from the Obama administration have taken to writing books that either entirely encompass, or are in some way related to their time in the White House. Yourself, of course, Alyssa Mastromonaco (‘Who Thought This Was A Good Idea? – And Other Questions You Should Have The Answers to When You Work in the White House’), Ben Rhodes (‘The World As It Is – Inside The Obama White House’), and Dan Pfeiffer (‘Yes We (Still) Can’).Do you think there’ll be as many folk with stories to tell at the end of the Trump administration?
“There will always be an appetite for insider-y looks at any White House. However, I think it’s safe to say that most Trump staffers’ books would serve better as guides on how not to run a White House.”
What really struck me most, Pat, and surprised me most too about Alyssa’s book when I first began reading that, was how funny it was. I don’t think I was expecting a book about politics – and I know now, in fairness to Alyssa, that it’s far from just being ‘about politics’ – to be funny. Because of the atmosphere and work environment, and the people that Alyssa mentioned and described in her book, I think I was a little less surprised that yours seemed to have such a strong sense of your own sense of humour in it. But also of the sense of humour of the White House at that time, including President Obama and Vice-President Biden. Looking back on it now, how important do you think it was to have that freedom really, for people to be able to express that side of themselves in such a high-pressure, intense workplace? And also, was that atmosphere something that developed organically, or was it designed in as much as possible by the leadership within the White House?
“I’m glad the humor came through. I definitely did not want to write a stodgy political book. Part of the point I was determined to make was that politics and public service can be fun without being totally dysfunctional. I can’t overstate how important it is to be able to laugh at yourself and with others throughout the day when you’re working in a high-stress environment like the West Wing. It’s like that cliché about taking your work seriously, but not yourself. That’s a mantra the Obama White House lived by from the top down.”
You remarked a few times in your book about how you’ve always been a worrier in normal life, but weren’t really at all in the White House because somewhere in the back of your mind you felt like it would never end. After six years of working there, for President Obama, and around so many dedicated, and inspiring people, what do you think are the most important personality or character traits that you’ve developed in that time? And in a sense, because of that time. I assume that, having come through your time in the West Wing, the whole worry thing in normal life is pretty much redundant now?
“Well, I’m still certainly a worrier, but I’ve also learned to take a longer view of things, not to get so caught up in the worry and frenzy of the moment. I was always amazed at President Obama’s ability to do just that, and I am trying to be better that way – to emulate that characteristic. In terms of the most important personality or character traits, I think working with so many different members of the press in such stressful environments forced me to get better at working with lots of personality types. The ability to sort of go with the flow and adapt on the fly was crucial in that job and I hope that will serve me well in the future.”
Yourself, and indeed the rest of the Obama administration, seemed to work so well with the press during President Obama’s time in office. With the odd exception here and there, I’m sure (adapters in the water, and such like…read the book!). Firstly, considering you had such a close relationship with the press pool for so long, what goes through your mind when you hear Trump repeatedly referring to the press as the ‘enemy of the people’, and the media (most of it) as ‘fake news’? And secondly, do you think Trump’s attitude towards the press and the media has kind of caught them off-guard in its persistent viciousness, absolute disregard for facts or the truth, and how easily so many Americans seem to be buying into that?
“In the Obama White House – like most White House’s before us – we upheld the natural, healthy tension that exists between the president and the press. Sure, they got on our nerves, and we certainly got on theirs; but we always remembered that we weren’t the only public servants who went to work at the White House. The press were and are just as important as the staffers who serve the president. After all, we call it The People’s House for a reason.”
Pat continued, “I think President Trump’s outrageous attacks on the free press are as dangerous as anything he’s done in office. It’s despicable, and it’s often hard for me to believe it’s happening here in the United States. I would say it’s caught them at least a little off guard. I think there was this idea that he’d be slightly more respectful after assuming office. It’s certainly caught me off guard, and it’s only made the work of the press even more crucial than it once was. I imagine it’s a lot harder for them now, too – what with the leader of the free world riling up his supporters against them in such a vicious manner. But, in the face of that unprecedented opposition, I think they’ve done a remarkable job of rooting out the truth.”
I certainly don’t recall any politician, either in the States or here in Europe, indeed, in my lifetime or before it, who has continued to hold rallies AFTER being elected. And seemingly, only to appeal to what everyone refers to as his ‘base.’ From somebody on the outside looking in, it’s definitely a strange turn of events, to put it mildly. What’s your own view on it?
“You know President Obama often held events – but they were in service of a policy or agenda that he thought would be good for the American people. President Trump seems to be holding events simply to stroke his own fragile ego.”
Twitter has changed the world in so many ways when it comes to communication. The fact that it’s instant, that it’s so direct, that it’s worldwide. What nobody could have ever imagined, I think, is how Twitter would change the Presidency, even if it does turn out to be (hopefully) for just this one term. From here on out, how do you see the role of, and the methods of, communication changing as far as the Office of the President is concerned? Both as a result of technological developments such as Twitter as platforms for communication, but also taking into account how this administration all but abandoned protocol in that area?
“It’s an interesting question. White House communications teams and plans have always had to evolve with changing technology. The Obama campaign was especially adept at it in 2007 and 2008, and we worked hard in the White House to keep up with the changing media environment and to “meet people where they are.” At the same time, I think the current presidency is an anomaly and we will revert to more traditional, respectful discourse from the Oval Office. But it will remain incumbent on all presidents to connect in new and creative ways with the American people, both to convey their own messages and – probably more importantly – to understand what’s on the minds of those across the country – but to do so in a manner befitting the awesome power and responsibility of the office he – and hopefully soon she – holds.”
Now, I know from your book that your Nana was, and I suppose still is, a massive fan of President Obama, and also very aware politically. Now that you’re out of politics, do you two still discuss what’s happening in the political realm, and if you do, what does she make of it all right now?
“My nana remains as spunky as ever. She’s getting much older, so I try not to get her too upset by bringing up President Trump too often. Truth is, I feel very sad for her. Here she is, a woman who’s fought for her rights her entire life, who has been incredibly involved on a local level – knocking doors, protesting, petitioning – and I, and I suppose she, thought it would culminate in her lifetime with the election of our nation’s first female president.”
You worked at the White House, Pat, not just for a long time, but really when you think about it, for most of your actual working life so far. That being so, how hard is it to deal with life away from a world where the days – and even the hours and the minutes within those days – were usually of real consequence? And is there any sense now that life has become boring? Or have you tried to consciously guard against letting that feeling creep in at any stage?
“It’s true, my first real job was working in the White House. I went straight from college, at 22, and didn’t leave until I was 29. So, in a way, I grew up there. It still sort of feels like I’m just on a long break from work and that one day the whole Obama crew will get together and head back to work. It’s still weird that it’s actually over. But I’ve had fun working on other projects like the book and TV shows and some other fun things I have in the works. But, yes, I do miss it and my wife did often warn me that it was going to be basically impossible to find something that matches the intensity and meaning of my first job!”
So you’ve essentially lived what would be seen as the pinnacle of many other peoples’ lives before you’re even out of your twenties.
Is there any kind of fear or worry about what comes next? And not just over the next few years, but in the longer term, too. Do you ever wonder if anything in the rest of your life will match the energy, and emotion, and uniqueness of what’s already been? Is it a high that you feel under any kind of pressure – internally or externally – to try and find again somewhere?
“Ha, yes! I’m just 30 now, and I don’t really have any clue what I want to be doing five years from now. But I’m having fun figuring out what that next exciting thing will be. I guess you could say I’m still winging it…! Truth is, I realize how privileged I was to have had this experience and that I may very well never have one like it again. But I’ve been fortunate to get involved in some other exciting opportunities, from TV to writing to volunteering on my mom’s campaign for Congress. And it’s been fun watching what all my former Obama-world co-workers are up to. Even the Obama’s themselves are exploring new opportunities like the one they signed with Netflix.”
In your book, you recall a moment when you were standing in a room after Sandyhook, waiting while the President met with the victims’ families backstage. And while looking at the front-row, it dawned on you that there wasn’t really a front-row per-say in the room that day because everybody who was going to be in there was directly impacted. It’s quite a powerful passage, and I can’t imagine what it must have been like to be in your position right then. Or indeed, President Obama’s. Were there any other moments like that, when almost all of a sudden, you became so vividly aware of the weight of the moment on your shoulders?
“It’s hard to say, but this question really is what makes working at the White House unique. Any day can turn on a dime. You can fall into feeling like you’re working at any old office and then – like a bolt of lightning – the president walks in, or important news breaks across the globe. I remember feeling this sense of what-in-the-world-am-I-doing-here impostor syndrome when we were flying down to South Africa with former President George W. Bush and Laura Bush, as well as Secretary Clinton, and of course President Obama, for Nelson Mandela’s funeral. But the truth is I felt that way every time I walked through the White House gates. I heard someone once say that the day you don’t feel nervous – that the awe of the place doesn’t hit you as you approach – then it’s probably time to leave.”
Your mum is a Professor of Writing and Rhetoric. So it’s probably fair to say that it’s from her that you get at least some of your own flair for writing. As well as your own natural talent, too, of course. Would you say that your mum’s influence and encouragement, in the writing side of your life, was a big factor in preparing you for your life in the West Wing? And ultimately in helping you to be as good as you were at your job during your time in the White House?
“My parents were and are a tremendous influence on me: my dad because he’s probably the hardest working guy I’ve ever met, and my mom because of her love for writing. I remember she made me read Strunk and White’s writing guide and she would reference it so often you would think they were family friends. My mom and dad played a huge role in my time at the White House, and they never failed to remind me that I needed to “stay and turn out the lights,” if ever I was considering leaving. I took their advice and stayed until the end, and I am very grateful I did.”
President Obama is a big hero of mine. That’s something that I freely, happily, and proudly admit to anyone. Anytime. Anywhere! And because I also write, I’m fascinated by what your process and technique was for finding ‘his voice’ first of all, and then for being able to write ‘in his voice’ for all those hundreds of pages that you did. So, if you don’t mind sharing a little bit, or everything, about that part of what you did…how did you do it??
“I started out writing suggested answers in his many, many interview memos – so I had a lot of practice before I ever wrote anything that went out directly from him. Other than that, it was a huge benefit to work as a wrangler and travel to hundreds of his speeches in 2011 and 2012 where I would listen from the buffer zone by the stage as he delivered countless speeches. So his voice sort of seeped into many of his staffers minds. My wife Stephanie would often call me out when I used an Obama-ism in real life, like when I slipped into writing about “hope and change” to our landlord, when – in reality – I just needed him to fix our air conditioning!”
You say in your book, Pat, that President Obama rightly considers himself to be a writer. And everybody knows about his love of reading. But most people will probably have no idea that he used to read ten letters a night from people from all over America to help him get a better sense of what was going on in the lives of those ‘ordinary, everyday’ Americans. I think letter-writing, sadly, is becoming something of dying, if not already lost, art. As a writer yourself, do you still write by hand at all, and do you ever write letters?
“I do. I still take lots of notes by hand and write out to-do lists (mainly for the pleasure of crossing items off the list). I’ll occasionally write a letter, but I should do it more. I want to emphasize the letters. Even while some were emails and not hand-written, it was a really important way for President Obama to pierce through the bubble that exists around any president – to connect, and understand a little bit better those he was elected to serve. All presidents would be well-served by upholding the tradition.”
Leaving aside the fact that you managed to get two jokes into President Obama’s speech for his last White House Correspondents Dinner…what would you say are your three most cherished memories from your time working in the West Wing of President Obama’s White House?
“Well, I did get engaged in the Rose Garden to my grade-school sweetheart and now wife Stephanie, so I suppose I should start by including that! It’s hard to choose a second – there are too many! But I will say election night 2012, after months of travel and worry, was pretty fantastic. Seeing the President and First Lady backstage after he delivered his victory speech and knowing that I was a very small part of something so wonderful, was really rewarding. Then, lastly, it would absolutely be election night 2016 and the morning that followed. We all know what happened. I was in the Press Secretary’s office partying with co-workers watching the returns come in. Then, of course, everything went badly, and we were drinking for a whole different reason. I’ll never forget being in the Rose Garden around midnight – where I had proposed to Stephanie a few years before – and thinking this can’t be how my time here ends. And then leaving the White House that night knowing that walking back in would never be the same.”
Pat went on, “But the memory doesn’t end there. The next morning, shocked, angry, depressed, I walked through the rain and gathered with the same co-workers in the same office as the night before. Only this time we were consoling each other. And then the President’s assistant, Ferial, popped her head in and said the president wanted to see us in the Oval Office. So we all streamed in. And he started to give us a pep talk about how hope is called for most in our losses, not our victories – and that history doesn’t move in a straight line; it zigs and zags. At this point, I was full-blown ugly crying. Then he turned and looked toward the Rose Garden where it had stopped raining. He told us he wanted to deliver the same message he just gave us to the American people. But he wanted to do it outside where it’s more optimistic.”
Pat concluded, “That’s a morning – and a pep-talk – I’ll never forget.”