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The best books on the Trump presidency

By Kobo • January 06, 2023Big Ideas in Books

Essential books for understanding the events and enduring significance of the administration of Donald J. Trump, the 45th president of the United States.

Though books are still being written, even as the former president gears up to take another run at winning the White House despite numerous legal issues in play, the books written during and immediately after his term tended to land in one of several groupings. There were the views from inside the White House, sparked by Michael Wolff’s Fire & Fury. There were the personal testimonies of confidants to the president and First Lady Melania Trump. There were the big picture analyses of what it all means—and might end up meaning. In the months following the events of January 6, 2021, there were books that attempted to sum up Trump’s political and cultural influence through the 2020 election, through to the inauguration of his successor Joe Biden.

We’ve assembled the essential reads in each of these categories to give readers a quick path to understanding what this era was all about—and what it might lead to.

Who is Donald J. Trump?

Trump: The Greatest Show on Earth—The Deals, the Downfall, the Reinvention by Wayne Barrett

Originally published in 1991, shortly after the release of Donald J. Trump's own ghostwritten book Trump: The Art of the Deal, Village Voice reporter Wayne Barrett's study of the real estate mogul focuses on how he made Trump Tower happen, which was at the time Trump's crowning achievement. Barrett shows Trump operating in a domain he knows well—Manhattan real estate—employing every available tactic, no matter how questionable, to get the deal done. Barrett digs into Trump's biography to deliver a portrait of the mogul at the peak of his powers, just before his run of bankruptcies in the 1990s, and more than a decade before his comeback via The Apprentice TV series.

Long-regarded as the definitive account of Trump's real estate dealings in Manhattan, the book was updated and re-released in 2016, following Trump's entry into the presidential race. Wayne Barrett died at age 71 on January 19, 2017, the day before Trump was inaugurated.

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Confidence Man: The Making of Donald Trump and the Breaking of America by Maggie Haberman

Pulitzer Prize-winning New York Times reporter Maggie Haberman covered the White House throughout the 45th presidency, and in this lengthy 2022 book she reveals insights from hundreds of interviews with Trump's personal and professional associates. The picture that emerges is of a person whose most enduring relationships are transactional, and for whom organizational chaos brings comfort.

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Disloyal: A Memoir by Michael Cohen

Michael Cohen served as Trump’s personal attorney from 2006 until he was sentenced to three years in federal prison in 2018 for tax evasion and campaign finance violations connected to the 2016 campaign. Disloyal is Cohen’s score-settling account of his former boss’s scandalous behaviour behind closed doors—and it likely cost him a presidential pardon.

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Rage by Bob Woodward

When renowned Washington Post reporter Bob Woodward released Fear, his first book on Trump, the president immediately got him on the phone to say that the book would be “bad” on account of Woodward failing to penetrate the defenses of White House staff that kept Trump out of the reporter's reach. In Rage, Woodward takes up Trump's offer of access; this book includes lengthy and revealing passages of the president musing on everything from his relationship with North Korean leader Kim Jong Un to the day-to-day experience of Black Americans.

Then in 2022...

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The Trump Tapes: Bob Woodward's Twenty Interviews with President Donald Trump by Bob Woodward

Woodward took the unprecedented step of releasing the actual audio recordings of his nineteen interviews with the president (and an interview from the 2016 campaign trail) in this audiobook so listeners could hear the president's words directly.

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The view from inside the Trump White House

The Divider: Trump in the White House, 2017-2021 by Peter Baker and Susan Glasser

Journalists Peter Baker and Susan Glasser team up to present an exhaustive account of the Trump presidency including scenes of high absurdity and grave peril which they learned of through interviews with foreign officials, legislators, and even the Trump family. Through these accounts they argue that rather than following whimsy and impulse, President Trump was learning day by day how to emulate the foreign dictators he most admired. Meanwhile, those around him drew and redrew their moral boundaries while working to limit the harm caused by a man they considered unfit for office.

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A Higher Loyalty: Truth, Lies, and Leadership by James Comey

When it was first published, the main question readers wanted the former FBI director to answer was, “why announce a re-opening of the investigation into candidate Hilary Clinton’s emails just days before the election, and when previous investigations turned up nothing illegal?” With such electoral tactics now absorbed into the fabric of history, Comey’s book offers readers the perspective of a senior government official with a history in prosecuting high profile individuals such as mafia dons and celebrities as he gets to know his new boss, President Trump. Comey’s shock is palpable in his narration of the audiobook.

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A Very Stable Genius: Donald J. Trump's Testing of America by Philip Rucker and Carol Leonnig

Pulitzer Prize-winning journalists Rucker and Leonnig take as much of a long view as is possible in this book that analyzes the principles and values that fuel activity in the Trump White House. What they find is that ideology isn’t the primary focus: personal loyalty to Trump himself trumps all else. Rather than chaos, they observe a clear pattern of actions that always come back to expanding the president’s power and protecting his image—no matter the cost.

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A Warning by A Senior Trump Administration Official

Here is a first-hand account by an anonymous source who was billed only as “A Senior Trump Administration Official” at the time of publication—who was later revealed to be Miles Taylor, the Chief of Staff to the Secretary of Homeland Security. Unlike the books above, this one comes from a single perspective formed over the seven months he served in office in 2019.

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I’ll Take Your Questions Now: What I Saw at the Trump White House by Stephanie Grisham

White House Press Secretary Stephanie Grisham resigned from her post on January 6, 2021 in response to the president’s response, or lack thereof, to the attempted insurrection. Well-known for restricting access and taking no questions in the nine months she held the top communications job in the White House, Grisham purports here to be telling it like it is about the administration, the Trump family, and the goings on during her tenure. While readers should take all of this with a grain of salt, it’s remarkable testimony nonetheless.

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The waning days of the Trump administration

I Alone Can Fix It: Donald J. Trump's Catastrophic Final Year by Carol Leonnig and Philip Rucker

From the reporting team that delivered A Very Stable Genius here is a portrait of how the Trump White House handled the COVID pandemic and the protests of summer 2020. From the earliest whispers of something concerning happening Wuhan, to the president’s promise that everyone will be able to attend Easter church services safely, to his desire to send the military to squash civil unrest, to the launch of the campaign to deny the outcome of the 2020 election, Leonnig and Rucker paint a damning portrait of an administration lashing out blindly and those who enabled it.

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The Plague Year: America in the Time of Covid by Lawrence Wright

Pulitzer Prize-winning journalist Lawrence Wright tells the story of COVID-19 in America, covering the early days of the CDC’s troubled test kit development, as well as the researchers whose foundational work allowed for the rapid development of vaccines. This is a broad view of the pandemic that includes the perspectives of scientists and healthcare professionals as well as small business operators and financial prognosticators. Wright shows the impact of the White House’s action and inaction throughout this historic year.

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Frankly, We Did Win This Election: The Inside Story of How Trump Lost by Michael C. Bender

Wall Street Journal reporter Michael C. Bender covers the period spanning Trump’s two impeachments, which includes the 2020 election that resulted in Trump’s loss and the ensuing fight to overturn the results. Bender combines interviews campaign advisors and senior administration officials with memos and emails from the campaign to illustrate how the president and is campaign staff were thinking about the electorate and their competition. And Bender connects the dots from key campaign messaging to the deadly January 6 attack on the US Capitol.

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Where does Trumpism go from here?

The Presidency of Donald J. Trump: A First Historical Assessment by Julian E. Zelizer

Princeton University historian Julian E. Zelizer has published a "first historical assessment" of every president since George W. Bush, assembling writing by scholars working in a variety of fields and from different political leanings to provide a balanced and critical view (in the most serious sense) of these presidents' terms. This book contains some of the first analysis of the Trump presidency written by scholars after he left office in January 2021.

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The Undertow: Scenes from a Slow Civil War by Jeff Sharlet

Reporter Jeff Sharlet attempts to untangle the contradictions of contemporary America, in which religious leaders preach the virtues of materialism while preparing for armed conflict, political movements coalesce around the annihilation of out groups rather than shared policy interests, and patriotic martyrs are made from participants in an insurrection. For Sharlet, "fascism" isn't the dirty word that most mainstream media outlets treat it as, but rather an accurate label for a political movement with deep American roots.

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The Road to Unfreedom: Russia, Europe, America by Timothy Snyder

Historian Timothy Snyder sets out to explain one of the biggest questions looming over geopolitics over the last decade: why is Russia interested in influencing and undermining the electoral processes of western countries? Snyder explains how Russia exercised power in the past, how the end of the Cold War created a new set of incentives and opportunities, and what Russian oligarchs stand to gain from a world destabilized by anti-democratic populism.

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Peril by Bob Woodward and Robert Costa

For his third book on Trump, Bob Woodward enlisted the help of his Washington Post colleague Robert Costa. The pair conducted interviews with more than 200 people and collected confidential documents and emails to give readers a view into the final days of the Trump administration and the first 100 days of the Biden presidency. Readers of Fear and Rage will want to hear this final word from Woodward.

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Why We Did It: A Travelogue from the Republican Road to Hell by Tim Miller

For decades Tim Miller worked as an operative for the GOP, most recently as communications director for Jeb Bush's 2016 presidential campaign. In the past he'd worked on the 1998 Colorado gubernatorial election, served as an Iowa staffer for John McCain in 2008, and national press secretary for Jon Huntsman's 2012 presidential campaign. In this darkly comic book, Miller narrates his own political career, and how the rise of candidate Donald Trump challenged his core beliefs about the party's values—leading him to leave in 2020.

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Why We're Polarized by Ezra Klein

Ezra Klein, co-founder of the political website Vox, offers a deeply-researched take on the social pressures pushing people to the edges of ideology. Klein offers readers a way out of the media bubbles and feedback loops and allows them to see themselves in a political context apart from the partisan vitriol, while also getting a peek at what a more productive political landscape might look like.

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Photo by History in HD on Unsplash

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