Humanities › Literature 5 Bestselling Books You Have to Read to Understand Donald Trump Share Flipboard Email Print Mario Tama / Getty Images Literature Best Sellers Best Selling Authors Best Seller Reviews Book Clubs & Classes Classic Literature Plays & Drama Poetry Quotations Shakespeare Short Stories Children's Books By Jeffrey Somers Literature Expert B.A., English, Rutgers University Jeff Somers is an award-winning writer who has authored nine novels, over 40 short stories, and "Writing Without Rules," a non-fiction book about the business and craft of writing. our editorial process Facebook Facebook Twitter Twitter Jeffrey Somers Updated January 22, 2020 These are pretty tumultuous times, politically, and people from all over the political spectrum are struggling to catch up with the new reality of the Trump Administration. Whether you voted for President Donald Trump or not, there’s a good chance you’re playing catch-up; the only certainty these days is that Trump is not like any President who has ever served. Even his supporters are having some trouble understanding the new President, and long-serving politicians who have dealt with several presidents are stymied, confused, and often uncertain how to proceed. If a six-term senator doesn’t know what to think, what hope do the rest of us have? As usual, books come to the rescue. It’s a rare president who doesn’t come to office with several books about them or by them already on the shelves, and Trump is no exception to this one pattern (although rumor is the President doesn’t read books, only magazines and newspapers). One of the great things about our time is our unprecedented access to information. Sometimes that means extreme convenience but sometimes that means old-school absorption of knowledge from a well-researched book. If you’re less than confident in your understanding of Trump’s philosophy of government, his conception of the office of the presidency, or his opinions on the wide range of issues that he will have personal influence on over the next four years, the following five bestselling books offer plenty of insight into Trump’s view of the world, his political goals, and what his manner of governing is going to be. 01 of 05 The Art of the Deal If you want to truly understand what’s shaped the 45th President’s thinking, why not start with this classic book of business advice and memoir? The book was written (or ghostwritten, as Tony Schwartz wrote it based on about eighteen months of meetings with Trump and observation of Trump’s daily activities) thirty years ago when Trump was just forty-one, and long before he had any concrete political ambitions, it’s true. But it remains the iconic Trump handbook, and it’s a book Trump has never disavowed or stopped promoting, so it obviously still represents his thinking. Donald Trump, after all, isn’t a man who’s shy about expressing a negative opinion, or about changing his mind. The fact that he still endorses a book he published thirty years ago is meaningful. It’s also key to understanding our new president because Donald Trump obviously believes very strongly that his experience and success as a CEO equips him to be an effective president. While the idea that business leaders have the skill set to lead the country is an old-school conservative belief, if Trump truly thinks his business experience and acumen is what will make him a successful Commander-in-Chief, then reading the book that lays out his business philosophy can only help you figure out what he’s doing, and why. After all, Trump continues to define political success in terms of “deals,” showing that he does view running the country as a series of negotiations, which is exactly what The Art of the Deal is all about. What’s been fascinating is the way Trump’s opponents have tried to turn this against him by noting all the times he fails to follow his own advice when dealing with foreign governments and other officials in the government. This line of attack is likely to increase over the next four years, so reading this book will give you insight on that end as well. 02 of 05 The America We Deserve Of course, this isn’t the first time Donald Trump has considered running for president. Way back in 2000, before hanging chads were even known to exist, Trump considered running for President as the Reform Party candidate. Since he didn’t have any political experience or track record, he did what aspiring politicians always do: He wrote a book. Enlisting the assistance of Dave Shiflett (who actually wrote the book, and who has called it his “first work of fiction”), Trump produced The America We Deserve, which was intended as a guide to his views on a wide variety of issues, a foundation he could use in a run for president. That run never happened; Shiflett claims that Trump never had any intention of actually running, that he was just seeking headlines and looking to raise his profile a little. Whatever his reasons, Trump bowed out and Pat Buchanan ran for the Reform Party that year. Still, The America We Deserve is the first attempt Trump made to codify his beliefs and his political philosophies. While the thinking (and many of the issues addressed) are nearly two decades out of date, they’re an excellent place to begin. If you can see where someone starts off in their thinking, then you can trace their development and evolution, gaining insight into their thought process. And while Trump didn’t actually write any of these words, he approved them, and Shiflett crafted them with feedback from the man himself, so they represent Trump’s beliefs at the time. 03 of 05 Great Again Once you’ve digested where Trump began in his political and presidential thinking, you can update to his most recent book on the subject, Great Again (formerly titled Crippled America). After all, this is the book he produced to clarify where he stood on the issues and positions that actually got him elected in 2016, so there is no more accurate or up-to-date book out there. It’s also vital to read Great Again because he actually contradicts many of his previously-state positions on issues such as gun control; whether this represents a thoughtful evolution of his beliefs or a calculated decision to woo voters is up to you, but if you’re seeking the current information on where Trump stands on a wide variety of things, anything he wrote before 2015 may or may not represent where his thinking is today. Of course, the presidency is a complex and difficult job and no doubt his views and beliefs will change again and again over the next four years as he gains new information and new experience. Since he’s unlikely to write a new book while in office, Great Again will remain the closest thing you’ll have to a Trump Rosetta Stone, at least for the time being. 04 of 05 Insane Clown President Taibbi mimics Hunter S. Thompson’s classic Fear and Loathing on the Campaign Trail ’72 with this collection of reports from the campaign trail that attempt to put Trump’s election into context and explain his victory. Taibbi shares with Thompson a belief that the American politician and the American voter are both deranged in different ways, and his book is sitting on the bestseller lists because people desperately want to understand how an outsider like Donald Trump won it all. In that sense, this book is essential, because if you want a clue as to how Donald Trump will run his administration, read up on how he ran his campaign. This is especially true since the early days of the Trump Administration imply he will use very similar tactics, at least at first. You can’t blame him, after all; he won the election, so no matter what you think of his tactics, they work. Whether they will work in the new context of actually being president remains to be seen. But since those tactics will be employed, reading Taibbi’s book is a great way to get the jump on what the Trump administration might do going forward. 05 of 05 Hillbilly Elegy This book isn’t about Donald Trump and doesn’t discuss him or his campaign, and yet it’s probably one of the most important books out there if you want to understand the folks who voted for Trump and who continue to support him. This book is especially crucial for people who don’t understand how it all happened and who find themselves confused and upset about the new political reality we’re all living in. Vance has written a memoir ostensibly about his life, born to poor parents in Kentucky who later move to Ohio, living in the middle of the Rust Belt. But as many have noted, the book is really about a certain segment of the American population that has been struggling with challenges for decades or longer, challenging that, from their point of view, never seem to get better. That a large portion of this population segment decided that voting for “establishment” candidates was getting them nowhere and that taking a chance on Donald Trump couldn’t make things worse is one of the most fascinating takeaways from the 2016 election. Since the continued support of these people is vital for Trump’s agenda, understanding them is necessary. Vance doesn’t speculate on politics much in the book and doesn’t offer any direct explanations. But if you want to know how Trump got into office and how he might continue to have enough support to get his agenda passed, start with this fascinating book. It will at least give you a glimpse into a mindset you might not be familiar with, but as we’ve all learned recently, bubbles are a problem and need to be eliminated wherever possible.