10 2020 Presidential Election Books That Shape Expert Perspectives

Curated by Joe Pags Pagliarulo, Rudy Giuliani, John Heilemann, offering deep insights into 2020 Presidential Election Books

Joe Pags Pagliarulo
Rudy Giuliani
John Heilemann
Judy Woodruff
Jake Tapper
Mehdi Hasan
Josh Dawsey
Updated on June 29, 2025
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What if I told you that the 2020 Presidential Election, one of the most contentious in recent American history, continues to inspire in-depth exploration and debate? Its complexities and controversies remain a critical subject for anyone seeking to understand modern political dynamics and electoral integrity. The stakes of this election ripple into the future, making the analysis found in these books more relevant than ever.

Voices like Joe Pags Pagliarulo, a syndicated talk show host known for his insightful political commentary, and Rudy Giuliani, former mayor of New York City and Trump’s campaign attorney, bring firsthand perspectives to these works. John Heilemann, executive editor at The Recount, adds analytical depth with his expertise in political campaigns, while Judy Woodruff and Jake Tapper provide journalistic rigor. Their endorsements highlight the importance of these books for anyone eager to understand the 2020 election’s many facets.

While these expert-curated books provide proven frameworks and comprehensive perspectives, readers seeking content tailored to their specific interests, experience levels, and learning goals might consider creating a personalized 2020 Presidential Election book that builds on these insights. This approach allows you to dive into targeted aspects of the election that matter most to you, accelerating your understanding efficiently.

Best for insider campaign analysis
John Heilemann, executive editor at The Recount and a longtime analyst of presidential politics, found this book to be "incredibly engrossing—one of many reasons to buy this book. It's an important book for history, but it's also a big bowl of candy." His extensive experience covering elections gives weight to his recommendation, especially as he appreciated the book's vivid portrayal of the Trump campaign’s inner workings during a turbulent year. Heilemann’s endorsement signals to you that this account goes beyond surface-level reporting, offering a nuanced understanding of the political and personal forces that shaped the 2020 election. Alongside him, Judy Woodruff calls it "a book full of astonishing stories," reinforcing its appeal to anyone eager to grasp the complexities of this historic political moment.
JH

Recommended by John Heilemann

Executive Editor at The Recount, Political Analyst

Incredibly engrossing—one of many reasons to buy this book. It's an important book for history, but it's also a big bowl of candy. (from Amazon)

Michael C. Bender, a seasoned White House reporter for the Wall Street Journal, leverages five years of deep political reportage to dissect the 2020 presidential campaign with precision. You’ll gain an insider’s view on the Trump administration’s strategic decisions, from the initial confidence fueled by economic momentum to the unraveling caused by the pandemic, civil unrest, and political turmoil. The book offers detailed narratives such as campaign memos and candid interviews that reveal the tension inside the Oval Office and Air Force One, especially around pivotal moments like Trump’s reaction to Black Lives Matter protests. If you want a thorough understanding of how internal dynamics and external crises intersected to shape that election, this book is tailored for you.

New York Times Bestseller
Gerald R. Ford Foundation Journalism Prize
National Press Club Award for Political Analysis
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Best for election fraud investigations
Joe Pags Pagliarulo, a syndicated talk show host known for his deep dives into political issues, highlights how Christina Bobb’s firsthand perspective as a Trump attorney offers rare insight into the 2020 election's contested events. "Trump attorney @christina_bobb gives her first-hand view of what really happened in 2020 plus how we can avoid a repeat in '24," he remarks after engaging with the book and its interviews. His recommendation carries weight for anyone seeking a detailed, inside look at election controversies. Additionally, Rudy Giuliani emphasizes the book’s relevance for understanding both past and upcoming elections, underscoring its importance.
JP

Recommended by Joe Pags Pagliarulo

Syndicated Talk Show Host

Trump attorney @christina_bobb gives her first-hand view of what really happened in 2020 plus how we can avoid a repeat in '24. Her new book is , “ STEALING YOUR VOTE: The Inside Story of the 2020 Election and What It Means for 2024” -- great interview (from X)

Drawing from her dual expertise as an investigative reporter and attorney, Christina Bobb scrutinizes the 2020 election with a penetrating eye on the evidence and aftermath. You’ll explore detailed accounts of alleged election fraud, the political reluctance to investigate, and the resulting erosion of public trust. Specific chapters dissect tactics like vote dumping and media suppression, revealing the tangled roles of both major parties. This book suits anyone aiming to understand the complexities behind election controversies and the challenges facing future electoral integrity.

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Best for custom election insights
This AI-created book on the 2020 Presidential Election is crafted based on your background and specific interests in election strategies and controversies. You tell us which aspects you want to focus on, your current knowledge level, and your learning goals. Then, the book is written to provide targeted insights that match exactly what you want to understand, making complex political dynamics more accessible and personally relevant.
2025·50-300 pages·2020 Presidential Election, Election Overview, Campaign Strategies, Legal Challenges, Media Influence

This tailored book explores the multifaceted strategies and controversies of the 2020 Presidential Election with a keen focus on your unique interests and background. It examines key campaign tactics, legal battles, media dynamics, and voter behavior, providing a personalized roadmap that matches your specific goals. By synthesizing extensive expert knowledge, this book reveals the nuances of election integrity, political maneuvering, and public discourse, all tailored to fit your preferred learning path. This approach allows you to engage deeply with the election's complexities without wading through extraneous details, facilitating a focused and enriching learning experience that highlights the election’s enduring impact.

Tailored Guide
Election Strategy Insights
1,000+ Happy Readers
Best for frontline campaign journalism
Jon Favreau, founder of Crooked Media and former Obama speechwriter, recognized this book as "Outstanding" for its unfiltered look at the 2020 campaign's chaos. His deep understanding of political communication amplifies the book’s value, especially as it sheds light on the intense pressures journalists faced during that turbulent election cycle. This insight helps you grasp the media’s critical role and the personal resilience required to report truth amidst hostility. Alongside The Atlantic, which calls it "a quite revealing and powerful book," these voices underscore why this account is essential for anyone tracking political journalism today.
JF

Recommended by Jon Favreau

Founder of Crooked Media, podcaster, Obama alum

Outstanding (from Amazon)

During her intense coverage of one of the most unpredictable presidential campaigns in American history, Katy Tur offers a vivid chronicle of her experiences on the front lines. As an NBC News correspondent, she not only reports facts but also reveals the relentless challenges journalists faced, including direct intimidation and misinformation. You gain an insider’s perspective on the dynamics of political reporting, the realities behind campaign events, and the evolving role of women in journalism, especially in a hostile environment. Chapters detail moments where Tur navigates chaotic rallies and confronts falsehoods head-on, making this book a potent study for anyone interested in media, politics, or the 2020 election’s roots.

New York Times Bestseller
Recipient of 2017 Walter Cronkite Award
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Best for election aftermath scrutiny
Stuart Stevens, a seasoned political strategist with experience in five Republican presidential campaigns and author of eight books, discovered this detailed account during a pivotal moment in American politics. He describes "The Steal" as a vital release, offering a thorough and insightful exploration of the election's contested aftermath. His appreciation stems from the authors’ nuanced approach to unraveling complex political events, which reshaped his understanding of the 2020 election challenges. This perspective underscores why you should consider engaging with this narrative for a grounded view of recent electoral history.
SS

Recommended by Stuart Stevens

Political strategist and author

Today the very important book “The Steal” by Mark Bowden and Matthew Teague is released. Hear two of America’s best discuss their work with Maya Senecal and others. Fascinating conversation with insight into how they approached this critical work. (from X)

Mark Bowden's decades of investigative journalism at the Philadelphia Inquirer and his authorship of bestselling works like Black Hawk Down set the foundation for this detailed chronicle of the 2020 election upheaval. Alongside Matthew Teague, Bowden delivers a meticulous, state-by-state narrative capturing the intense weeks between the election and January 6, focusing on the efforts to overturn results in key battlegrounds. You gain insight into the roles of election officials, judges, and activists who navigated unprecedented challenges and threats while safeguarding the electoral process. The book’s strength lies in its granular recounting of events, making it especially useful for those seeking a factual understanding of the election’s contested aftermath.

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Best for political polarization insights
Brendan Nyhan, a professor at the University of Michigan and contributor to The New York Times, highlights this book as essential for anyone concerned about American democracy. Having observed the 2020 election's upheaval firsthand, Nyhan emphasizes how the book's findings challenge prevailing narratives about voter behavior and polarization. He calls it "a must-read" for understanding the election's complexities and what they mean for the nation's future, making it clear why this analysis is vital for grasping the current political landscape.
BN

Recommended by Brendan Nyhan

Professor at University of Michigan, NYT contributor

A must-read! My endorsement: "Anyone who cares about the future of American democracy needs to grapple with the findings in this book." (from X)

John Sides, a seasoned political scientist, along with Chris Tausanovitch and Lynn Vavreck, unpacks how the 2020 presidential campaign both reflected and intensified deep divisions in American democracy. You gain a nuanced understanding of the interplay between long-term partisan trends and the shocks of that year, including the pandemic and social unrest. The book lays out how voter loyalty, despite scandals and crises, shaped a tightly contested election and explores the paradox of entrenched polarization alongside moments of electoral shift. If you want to grasp the forces that shaped one of the most contentious elections in recent history, this detailed analysis will deepen your insight.

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Best for rapid election mastery
This AI-created book on 2020 election dynamics is tailored to your background, skill level, and specific interests. By sharing the aspects of the election you want to focus on and your learning goals, this book is crafted to guide you through the complex political landscape effectively. It offers a personalized path that highlights the critical events and strategies shaping the election, making your learning experience targeted and meaningful.
2025·50-300 pages·2020 Presidential Election, Election Overview, Campaign Dynamics, Political Strategies, Media Influence

This tailored book offers a focused journey into the 2020 election campaign, designed to help you quickly grasp the complex dynamics that shaped this pivotal event. It explores the key players, major events, and underlying forces driving the election, providing a clear pathway that matches your background and specific interests. By offering a personalized synthesis of expert knowledge, the book reveals how campaign strategies, media influence, legal battles, and voter behavior intertwine to impact outcomes. This carefully tailored approach ensures that you engage deeply with the most relevant aspects, supporting efficient learning without the need to sift through numerous sources, all aligned with your goals.

Tailored Guide
Campaign Dynamics
1,000+ Happy Readers
Best for election integrity clarity
Major Garrett is the Chief Washington Correspondent for CBS News and the host of The Takeout and The Debrief on CBSN. With over thirty years of award-winning journalism covering America's pressing issues, Garrett brings authoritative expertise to this examination of the 2020 election. His background provides a strong foundation for revealing the realities behind one of the most scrutinized elections in American history, making this book a compelling resource for understanding the challenges democracy faced during that pivotal moment.
2022·288 pages·2020 Presidential Election, Politics, Elections, Democracy, Election Security

Unlike most political books that recycle partisan arguments, Major Garrett and David Becker dig into the mechanics and realities behind the 2020 election, presenting a detailed narrative shaped by interviews with key figures like Liz Cheney and Brad Raffensperger. You’ll gain insight into how election officials navigated unprecedented scrutiny and false claims, learning to distinguish fact from politically motivated fiction. The authors challenge the widespread misinformation about voter fraud with evidence and firsthand accounts, offering a clear-eyed look at democratic resilience. This book suits anyone seeking a grounded understanding of the election’s integrity and the forces that threatened it, without partisan spin.

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Best for Democratic primary perspectives
Scott Adams, Chief Strategy Officer at WhenHub, brings a strategic lens to the 2020 election landscape. He highlights Joel Pollak's book during his Coffee with Scott Adams session, praising it as a compelling dive into the political tensions of the Democratic primaries. Adams' endorsement stems from his deep engagement with election dynamics and his appreciation for Pollak's on-the-ground reporting. His recommendation invites you to explore the ideological clashes and campaign realities captured in this timely work.
SA

Recommended by Scott Adams

Chief Strategy Officer, WhenHub

Join me on Coffee with Scott Adams at 10 AM ET featuring Joel Pollack talking about his great new book, Red November: via @amazon (from X)

2020·368 pages·2020 Presidential Election, Democratic Party, Socialism, Politics, Campaign Trail

Joel B. Pollak, a senior editor at Breitbart News with a background in law and politics, offers a firsthand look at the 2020 Democratic primaries from a conservative viewpoint. You get an insider's perspective on how socialism gained traction and how once-radical ideas became mainstream within the party, illustrated through campaign trail stories, candidate interviews, and media confrontations. This book is especially useful if you want to understand the dynamics within the Democratic Party during the 2020 election and the ideological battles shaping American politics. It's a sharp blend of travelogue, satire, and political memoir that challenges readers to see the election through an unconventional lens.

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Best for socialist influence exposé
Kash Jackson, a 20-year Navy veteran and outspoken patriot, highlights this book amid rising concerns about socialism and communism in America’s 2020 election. His endorsement stems from a deep apprehension about political shifts and the potential impact of candidates like Bernie Sanders. Jackson calls it a "phenomenal book" by Trevor Loudon, whose extensive research into Marxist movements unpacks the risks hidden within mainstream politics. This perspective offers you a lens to critically assess the ideological battles shaping the election.
KJ

Recommended by Kash Jackson

20-year Navy veteran and patriot

@TrumpWarRoom @marc_lotter To those who are concerned about the rise of Socialism/Communism in our country & the thought of someone like #BernieSanders rising to power, you MUST READ this phenomenal book that was written by Epoch Times Writer Trevor Loudon. @newzealblog (from X)

What if everything you thought about the 2020 presidential candidates was incomplete? Trevor Loudon, drawing on over 30 years researching Marxist and radical movements, exposes the hidden socialist and communist influences shaping key contenders for the Democratic nomination. You’ll gain insight into the backgrounds and security risks of ten high-profile politicians, with chapters detailing their affiliations and ideological leanings. This book suits anyone looking to understand the undercurrents influencing American politics in 2020, though its strong ideological stance may not resonate with every viewpoint.

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Best for cybersecurity election analysis
Patrick M Byrne holds degrees from Dartmouth, Cambridge, and Stanford, combining philosophy, Asian studies, and rigorous academic training with his entrepreneurial background. As a classical liberal concerned with education and markets, Byrne channels his expertise into this book to dissect the 2020 election events. His unique vantage point as a businessman turned investigator drives a narrative that delves into election fraud allegations, constitutional timing pressures, and the political environment shaping the electoral aftermath.
The Deep Rig book cover

by Patrick M Byrne··You?

2021·268 pages·2020 Presidential Election, Politics, Elections, Election Fraud, Cybersecurity

Patrick M Byrne’s extensive academic background and entrepreneurial experience underpin this detailed investigation into the 2020 election controversy. You’ll gain insight into the complex web of alleged election fraud through Byrne’s firsthand account of assembling a specialized team of "cyber-ninjas" to uncover hidden irregularities under intense political and legal pressure. The narrative goes beyond surface-level claims, offering a look at the interplay between technology, constitutional deadlines, and Washington’s inner workings. This book suits anyone seriously interested in electoral integrity, political processes, or the mechanics behind contested elections, though its perspective may challenge mainstream narratives.

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Best for technical fraud investigation
Gregory Stenstrom, co-founder of Patriot.Online and former US Naval Officer with expertise in computer sciences and fraud investigations, authored this book to document and expose what he and his colleagues identified as large-scale election fraud during the 2020 general election in Pennsylvania. His unique background in special operations and security lends authoritative weight to the detailed account of how counterfeit ballots were allegedly substituted for authentic ones, providing a rare insider perspective on the challenges of protecting electoral integrity.
The Parallel Election: A Blueprint for Deception book cover

by Gregory Stenstrom, Leah Hoopes, Lisa Schiffren··You?

2022·428 pages·Election, 2020 Presidential Election, Elections, Election Fraud, Legal Challenges

After analyzing detailed evidence from Delaware County, Pennsylvania, Gregory Stenstrom and Leah Hoopes expose how a massive fraud operation during the 2020 United States general election replaced authentic ballots with counterfeit ones. Drawing from Stenstrom's background in computer science, security, and fraud investigations, the book meticulously lays out the mechanics and actors involved in what they term a "parallel election." You gain insight into the legal battles and challenges they faced while defending their findings against official denials. This book suits readers interested in election integrity, legal processes, and the technical aspects of electoral manipulation.

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Conclusion

Taken together, these 10 books illuminate the 2020 Presidential Election from multiple angles—campaign strategy, election integrity, media coverage, and the ideological battles that shaped the contest. They reveal how complex political narratives intertwine with legal challenges and voter behavior, offering you a multifaceted view of this pivotal moment.

If you're seeking to grasp the internal dynamics of the Trump campaign, start with Michael Bender’s Frankly, We Did Win This Election. For those focused on election integrity and fraud allegations, Christina Bobb’s Stealing Your Vote and Mark Bowden’s The Steal provide detailed investigations. And if you want to understand the broader political and ideological shifts, John Sides’ The Bitter End offers critical insights.

Alternatively, you can create a personalized 2020 Presidential Election book to bridge the gap between general principles and your specific situation. These books can help you accelerate your learning journey and deepen your grasp of one of the most consequential elections in recent history.

Frequently Asked Questions

I'm overwhelmed by choice – which book should I start with?

Start with Frankly, We Did Win This Election by Michael Bender for a vivid account of the Trump campaign’s inner workings. It’s accessible and richly detailed, providing a solid foundation before exploring other perspectives.

Are these books too advanced for someone new to the 2020 Presidential Election?

Not at all. While some offer detailed analysis, many like Unbelievable by Katy Tur provide clear, firsthand reporting suitable for newcomers seeking to understand the election’s complexities.

What’s the best order to read these books?

Begin with narrative-driven accounts such as Unbelievable and Frankly, We Did Win This Election, then move to investigative works like Stealing Your Vote and The Steal, followed by broader analysis like The Bitter End.

Do I really need to read all of these, or can I just pick one?

You can pick based on your interest—choose Red November for Democratic primaries or WHITE HOUSE REDS for socialist influence. Each offers unique insights, so select what aligns with your curiosity.

Are there any books here that contradict each other?

Some books present differing perspectives, reflecting the election’s contested nature. For example, Stealing Your Vote and The Big Truth explore opposing views on election integrity, offering a balanced understanding when read together.

How can I get election insights tailored specifically to my interests without reading all these books?

Great question! While these books offer expert insights, you can create a personalized 2020 Presidential Election book tailored to your background and goals. This bridges expert knowledge with your unique needs efficiently.

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