An Obamarama
Memoirs written by alums of the Obama administration and why this is my favorite genre
Fun fact about me: I have read nearly every memoir written by alums of the Obama administration. These memoirs range from low-level staffers (think: the stenographer), to high-level staffers (think: communications director, deputy national security director, and deputy chief of staff), to Cabinet level officials. These books hit a real reading niche for me so they are all highly rated. I start and end, however, with books that I rated 10/10, and make sure you read to the bottom for one of my favorite books of all time.
Obama was president during the formative years of my childhood. One of my earliest political memories is watching Obama’s first inauguration in Brian Fahey’s fifth grade classroom in awe of what was taking place. As I became older and more aware, the political backdrop of my adolescence was always competence and care. Even though I now know it was sometimes naive, I had faith in the system and believed that progress moved in a straight line towards a better future for everyone. My dream was to work in the White House when I was old enough, and as my eligibility neared, I was excited to be able to do it for the first female president.
After Hillary Clinton lost and Donald Trump won I was despondent. What happened to progress moving in a straight line? Using a unique coping mechanism, I started picking up the memoirs of former Obama administration officials as they were released. I started to read these books out of curiosity, general interest, and the hope that they would re-instill my faith in government. Many of these books were published around the summer of 2018, which coincidentally coincided with an internship I had in D.C.. Every morning I walked directly in front of the White House on my commute from Foggy Bottom to work. And so, to push aside the feeling of disappointment I had when I walked by and saw people standing with their red hats looking through the fence, I decided to project the stories of the memoirs that I was reading onto the building and into my idea of government. I looked at the path these staffers took to work in the White House, the ways they had honed their interest in their respective fields, and how I might maybe replicate it someday.
Thanks, Obama - David Litt
Speechwriter, 320 pages
This book is a hilarious inside-look at the life of a mid-level staffer in the White House. The humor of this book was heightened in audio format, which is how I read it, and I definitely laughed out loud multiple times. Litt was a speechwriter for Obama between 2011-2016. He wrote on serious policy issues like climate change and criminal justice, but was also Obama’s go-to for comedy, writing Obama’s famous speeches at the White House Correspondents Dinners. Litt writes like a guy who can’t believe he worked in the White House, which is fair because he graduated from college in 2008. Many of the experiences he relates show Litt and other young staffers like him stumbling through the corridors of power fueled almost exclusively by intense idealism. Their inexperienced proximity to power was made clear while Litt was preparing the speech Obama would give at the 2011 White House Correspondents Dinner, which in its first draft, was supposed to include a joke about Osama Bin Laden. In rehearsal the day before, Obama had to convince his writers to change the reference without giving any explanation. While Litt complains to readers that the speechwriting team thought the joke was funnier in its original form, he also writes that they had no idea that the Bin Laden raid would take place 3 days later, highlighting the proximity Litt had to important moments, while not quiet being in the room where decisions were made. I highly recommend this book. It is humorous and insightful, and a reminder of how idealism is not always a bad thing.
Rating: 10/10
From the Corner of the Oval - Beck Dorey-Stein
White House Stenographer, 352 pages
In her mid-20s, Beck Dorey-Stein became a stenographer in the Obama White House, working there from 2012-2017. Before she started working at the White House, Dorey-Stein was working odd jobs and trying to figure out what she wanted to do with her life. You’ll imagine her surprise when an ad she applied to on Craigslist ended up being an ad for a job in the White House - giving her book a similar “I can’t believe how I got here” attitude as Litt. Stenographers follow the president around all day recording his speeches and events and later transcribing them for posterity. Stenographers are also career civil servants, meaning that they are not tied to a single administration, although Dorey-Stein leaves the White House in 2017 because she does not want to work under Trump. As part of Obama’s entourage, Dorey-Stein got to travel around the country and the world, and she has funny and intriguing stories to match. However, if you are someone who is only interested in policy or high-level decision making in the White House, this book is not for you. Despite this, I do think that Dorey-Stein has an interesting perspective to offer readers. It’s not often that low-level staffers write and publish books, and her story is a reminder of all the people that it takes to keep the White House operational and functional.
Rating: 8/10
Yes We (Still) Can: Politics in the Age of Obama, Twitter, and Trump - Dan Pfeiffer
Communications Director and current co-host of Pod Save America, 304 pages
As Communications Director for Obama from 2009-2013 and then a senior advisor to the president from 2013-2015, Dan Pfiefer provides a unique perspective of high-level decision making in the Obama administration. Writing within the context of the Trump presidency, Pfiefer shares his experience working with Obama as well as his thoughts on how to escape the Trump era. While they both worked on the communications staff, Pfiefer’s book is different than Litt’s because of his high position within the White House. As a result, readers get an inside look from a person who had a seat at the table. For example, in 2009 as everyone went home for the holidays, Pfiefer recounts his experience dramatically needing to sequester himself from his family as the White House reacted to the attempted Christmas-day bombing on an airplane over Detroit. This story exhibits the all-encompassing workload of senior White House officials who dedicate their entire lives to the White House, eliminating any semblance of a work-life balance.
At times, however, Pfeiffer annoyed me with some of his anti-media views, especially considering the political climate in 2018, when this book was released. At a time when the president of the United States was calling the media fake news and the enemy of the people, I didn’t find it particularly productive for Pfiefer to continue to bash the institution at every turn, although I do agree with some of his assessments of the sensationalized way that Obama was covered. If anything, this perspective is indicative of the tense relationship that the Communications Director in any administration has with the press, and the challenges that the Director has in projecting a singular message of achievement to people who might not be interested in parroting prepared talking points.
As an aside: after I connected the dots that Dan Pfiefer went to my high school (!) I reached out to him on LinkedIn with the hope that he would feel some Friends alum pride and give me advice (or in my wildest dreams become my mentor and rocket my career forward). Pfiefer neither replied nor read the message. I recently looked back at what I sent to him and damn if it wasn’t a good email.
Rating: 8/10
Who Thought This Was a Good Idea? - Alyssa Mastromonaco
Former White House Deputy Chief of Staff, 272 pages
Alyssa Mastromonaco’s book is not just about her time in the White House as the Deputy Chief of Staff. Mastromonaco also worked for Obama while he was still a Senator, and played a crucial behind-the-scenes role in his 2008 campaign. Mastromonaco writes about her time working for Obama with humor and levity. This humor brings a human element to all the work that staffers do, and reminds readers that even in high-stakes or important situations, staffers are still people who experience embarrassing situations. Two stories in particular stand out. The first was during Obama’s state visit to the Vatican, when, just before her opportunity to meet the Pope, she was overcome with a crippling case of diarrhea that concerned the Secret Service agents on Obama’s detail and pulled her out of commission. In another story, Mastromonaco writes about how Obama surprised her by inviting her to his meeting with the Queen of England. The only problem was that on such short notice her suitcase had already been packed away, leaving her with only a pair of jeans to wear to meet the Queen. Mastromonaco describes Obama’s humorous embarrassment at her wardrobe, and then her efforts to stand behind taller people in the American entourage at Buckingham Palace with the hopes that no one would notice (spoiler: the Queen noticed).
I appreciated this book not just for the funny stories but also for the perspective that Mastromonaco was able to provide as a high-ranking female staffer. It’s not hard to notice that this list is comprised of the memoirs of mostly male, all white staffers, which points to the larger issue of the lack of diversity at the highest levels of the White House and in the halls of power generally. Mastromonaco was the first female Deputy Chief of Staff and it is in recognition of this that she positions her book not just as a memoir that recounts her experience, but also as encouragement for women and girls reading that they too can get inside the Oval.
Rating: 9/10
West Winging It - Pat Cunnane
Senior Writer and Deputy Director of Messaging, 320 pages
Cunnane’s role lands him somewhere in-between Litt and Pfiefer as to his access to the presidency and the decision-making process of the president’s team of senior staffers. However, this is a good middle ground for Cunnane to recount the duties of his job in the White House writing speeches for Obama and later shaping his messaging (fun fact: Cunnane co-wrote Obama’s famous appearance on Jerry Seinfeld’s Comedians in Cars Getting Coffee sketch). Much like the other memoirs in his class, Cunnane’s book centers heavily around his relationships with others in the White House, providing personalized descriptions of characters that readers might only know about from their professional bios or news reports. This book was definitely good, funny, and interesting (I rated it 9/10 after I finished reading it), but it did not leave a lasting impression. Indeed, I struggled to remember anecdotes or details specific to Cunnane’s story while writing this review. However, don’t let my bad memory dissuade you from picking up this book. The more inside stories from the Obama administration, the better.
Rating: 9/10
The World As It Is - Ben Rhodes
Deputy National Security Advisor, 480 pages
As Deputy National Security Advisor, Ben Rhodes’ book is focused on foreign policy. Unlike Litt, Dorey-Stein, and Cunnane, Rhodes was nearly always in the room when important decisions were taking place and despite his young age quickly became one of Obama’s most-trusted staffers. While Litt was left wondering why he had to remove a reference to Bin Laden in the 2011 White House Correspondents Dinner speech, Rhodes was in the Situation Room as the raid took place, indicating his proximity to important decisions and events. Every morning Rhodes was present as Obama read the Presidential Daily Brief, traveled the world with Obama on every foreign trip, was one of the lead negotiators in the opening of relations with Cuba, and was instrumental in the signing of the Iran Nuclear Deal in 2015. Rhodes worked at the White House throughout the entirety of Obama’s two terms, which is fairly unique amongst staffers with such stressful positions. The longevity of Rhodes’ tenure adds complexity and detail to his assessment of the Obama years, and readers can track the development of Rhodes and Obama’s thinking on foreign policy as the years go by. On top of all this, Rhodes is an exceptional writer. Initially, Rhodes wanted to be a full-time writer, but after September 11 he felt called to public service. He transferred his writing skills to Obama’s national security speechwriting team, and his talents are manifested in this wonderful book. I relished in Rhodes’ descriptions of foreign policy decision making, the ways that the Obama team had to grapple with complex issues of geopolitics, and how they came to understand the role America should play on the global stage.
Rating: 9.5/10
The Education of an Idealist - Samantha Power
US Ambassador to the United Nations, 592 pages
Power’s path to becoming the United States Ambassador to the United Nations feels improbable and pre-destined at the same time. Power was born in Ireland in 1970 and moved to the United States when she was a small child, leaving behind her alcoholic father in Dublin to live with her mother and step-father. In 1995, only a few years after Power graduated from college, she decided to move to Bosnia, right as the Bosnian Genocide was beginning. Without any formal journalistic training or even a newspaper to work for, Power headed straight into a war zone, determined to raise awareness about what was taking place and hopefully inspire the Clinton administration to do something to put a stop to the violence. Her experience covering the Bosnian Genocide shaped her dedication to calling attention to and ending atrocities around the world, ultimately providing the material for her 2003 Pulitzer Prize winning book A Problem From Hell. It was this book that caught Obama’s attention, and earned her a job offer on Capitol Hill while he was still a Senator. When Obama won the presidency, she was brought on to the National Security Council as a Special Assistant and later became the U.S. Ambassador to the UN in 2013, the youngest-ever U.S. Ambassador to serve.
Throughout her illustrious career, Power never lost her faith in the way America’s stature on the global stage could be used to end atrocities. The intensity in this idealism sometimes brought her at odds with Obama and other members of his team, but also earned her a reputation as a dogged worker intent on improving people’s lives. Like Rhodes, Power is an exceptional writer, and every part of her personal journey is interesting to read about and inspiring. This is not only the best book on this list, but also one of my favorite books of all time. I can only hope to accomplish a fraction of what she has accomplished.
Rating: 10/10
Given how long this has gotten, I am going to save my reviews of Becoming by Michelle Obama, Promise Me Dad by Joe Biden, and A Promised Land by Barack Obama for a future post. Until then, if you like what you’ve read or know someone who you think would enjoy this blog consider sharing and subscribing!
I've read a couple of these and they were really good. I haven't heard of a few of them. Off I go to add them to my TBR
Such fun suggestions, I can't wait to read these! Did you ever read Ron Suskind's book, Confidence Men? A somewhat critical assessment of the Obama administration in the first few years. Very interesting, and I think fair.