Donald Trump has treated book publishing the way he treats nearly everything else: as a stage, a deal, and a megaphone. The arc runs from a classic 1980s blockbuster—Trump: The Art of the Deal—to today’s high-margin, self-controlled coffee-table releases sold straight to his fans at premium prices. Along the way are testy ghostwriter dramas, splashy marketing stunts (yes, including $100 bills at a book event), and a late-career pivot that cut out the big houses almost entirely. What follows is the gripping backstory of those deals—how they were struck, where the money was, and why the playbook keeps changing.
The blockbuster that built the brand (1987)
The origin myth begins with The Art of the Deal, published by Random House in 1987. Part pep talk, part personal mythmaking, the book lodged itself on the New York Times list for 48 weeks—13 of them at #1. In the era of gold-rimmed excess, it minted a persona as much as it sold advice, elevating Trump from New York developer to national archetype. (Wikipedia)
Behind the scenes, the deal was unusually rich for a first-time business memoir. Trump and credited coauthor Tony Schwartz split a $500,000 advance 50–50—then shared royalties down the middle, a structure Schwartz has discussed repeatedly. Years later, when Schwartz criticized Trump, Trump’s lawyers even demanded Schwartz return the money, citing that original arrangement; Schwartz said the split included half the advance and half the royalties from the start. (The Guardian)
Schwartz also later described how thoroughly he shaped the text and how decisively Trump embraced the promotional value. Whether one sees the book as bootstrap gospel or brand brochure, it was an undeniable hit, and it still throws off royalties decades later—financial disclosures in the late 2010s showed Art of the Deal remained the rare Trump title that consistently earned real money. (The New Yorker)
Crash, rebrand, and “survival” (1990–1997)
The sequel era was less triumphant. In 1990, amid a very public financial slump, Random House rushed out Trump: Surviving at the Top. The publisher printed roughly half a million copies, riding momentum from the first book. Warner then paid nearly $1 million for paperback rights—and retitled it The Art of Survival to better match the times. The book still hit #1 briefly, but its run and reviews were choppier, mirroring its author’s fortunes. (Wikipedia)
By 1997, the narrative reset arrived: Trump: The Art of the Comeback (Times Books) retold the salvation story and reintroduced the swagger. It positioned the ’90s turnaround as the inevitable second act—another well-timed shelf-life extension for the Trump brand. (Wikipedia)
Reality TV rocket fuel and the self-help run (2004–2007)
When The Apprentice hit TV in 2004, Trump seized the moment with a rapid-fire run of “how-to” titles, often with ghostwriter Meredith McIver: Trump: How to Get Rich (Random House/Crown) and then, in quick succession, The Way to the Top and Think Like a Billionaire. The content blended boardroom bonsai—short, snappy commandments—with television glow. The books read like an extension of the show’s elevator rides: brisk, brash, image-forward. (Wikipedia)
The mid-2000s also produced a lucrative coauthoring lane. With Robert Kiyosaki, Trump published Why We Want You to Be Rich (2006), which debuted at #1 on the Times list and kicked off a mini-franchise that included Midas Touch five years later. It was cross-promotion catnip: two self-made mogul myths reinforcing each other’s audiences and touring together. (Wikipedia)
And then there was the pure spectacle of Think Big and Kick Ass (HarperCollins, 2007), coauthored with Learning Annex impresario Bill Zanker. The first printing reportedly ran to 400,000, and a New York promo saw Trump hand out $100 bills to early buyers—a literal cash-back guarantee on the hype. It was part publishing, part performance art, cut for the tabloid camera. (Wikipedia)
Politics on the page (2011–2016)
As Trump’s political ambitions edged forward, the books sharpened. Time to Get Tough (2011) previewed campaign themes; Crippled America (2015), from Simon & Schuster’s conservative imprint Threshold Editions, arrived as his candidacy took off. He hustled signed copies via a specialty retailer, turning the live-streamed signing into a mini-telethon and touting that the proceeds would go to charity. It was a forerunner to the later direct-to-base model: limited intermediaries, maximum attention. (Simon & Schuster)
Meanwhile, Art of the Deal returned to center stage—and not just on royalty statements. Schwartz publicly regretted the myth he helped craft; Trump’s lawyers fired off a cease-and-desist; the book’s origin story became a political subplot. The still-steady income from Art in those years underscored how one well-positioned property can out-earn a shelf of lesser follow-ups. (TIME)
The great rupture with the Big Five (2021)
Here’s where the tale turns. After leaving office, Trump claimed he’d received “two or three” offers for a memoir. The industry’s reporting told a different story: major New York houses kept their distance, citing fact-checking nightmares and staff blowback. Hundreds of editors and agents even signed an open letter urging publishers to skip a Trump memoir altogether. Whether you see that as principled, political, or purely practical, it ended the traditional play. (Business Insider)
Trumpworld’s answer was to cut the big houses out entirely. In late 2021, Donald Trump Jr. and GOP operative Sergio Gor launched Winning Team Publishing to produce and control Trump-aligned books in-house. The strategy was simple: own the pipeline, set premium pricing, and route sales through a friendly storefront—45Books.com—plus rallies and conservative channels, dodging the gatekeeping of mainstream retail. (Wikipedia)
The coffee-table era: high price, high control (2021–present)
Book #1: Our Journey Together (2021). The first Winning Team release was a glossy photo book of Trump’s presidency, sold initially at $74.99 unsigned and more for signed editions. It wasn’t a narrative memoir; it was a curated visual highlight reel with Trump’s captions—commentary dialed to Trumpian. The book also sparked controversy after reporting that Trump had blocked his former chief White House photographer Shealah Craighead’s parallel book project, then published his own using many of the same official photographs. (Craighead received limited acknowledgment but no byline alongside images.) The tabloid-grade drama only juiced interest. (Winning Team Publishing)
Despite the outrage, the business math worked. Forbes later tallied $5.75 million in royalties for Trump from Our Journey Together over an 18-month period—an eye-popping return for a picture book largely leveraging public-domain and official images. (Forbes)
Book #2: Letters to Trump (2023). Next came a compilation of 150 letters to and from world leaders and celebrities, priced at $99 ($399 signed). Think scrapbook diplomacy: Kim Jong-un alongside Oprah, Reagan beside pop stars. Whatever one thinks of the curation, the price positioning was the point—less airport impulse buy, more boutique donor merch. (The Guardian)
Book #3: Save America (2024). The latest entry doubled down on the coffee-table template—photos, captions, a campaign-season time capsule—released weeks before the election by Winning Team Publishing. Coverage clocked brisk early sales on Amazon’s category lists and a raft of mainstream reviews that criticized the design and propagandistic tone even as they acknowledged the book’s brand function. The cover, a raised-fist image shot moments after the July 2024 rally attack, made the thesis plain: iconography over introspection. (Wikipedia)
If the numbers are any guide, the micro-press model prints money. Trump’s 2025 disclosure indicated he earned about $3.4 million from Winning Team Publishing in the prior year—on top of earlier windfalls. The margins are obvious: direct sales, premium pricing, minimal fact-checking overhead, and a fanbase that treats a signed edition as both memorabilia and message. (Forbes)
There have been headwinds. At least one major airport bookseller chose not to stock Winning Team titles, limiting serendipitous discovery beyond the core audience. But that’s almost beside the point when the distribution plan is “talk to the base, cash the checks.” (Wikipedia)
The Trump book as product—and as strategy
Across four decades, Trump’s book deals have done three jobs at once:
- Cash generation. From a rich 1987 split with Schwartz to multi-million-dollar royalties on high-priced photo books, the pages pay. Even in his presidency and beyond, public filings and press tallies repeatedly show Art of the Deal and the coffee-table titles throwing off six- and seven-figure income. (Wikipedia)
- Image management. In down cycles, the books reset the story: Surviving at the Top explained the stumble; Art of the Comeback celebrated the rebound; Crippled America reframed politics as a repair mission. In up cycles, the “how-to” books leverage the spotlight—particularly during The Apprentice. (Wikipedia)
- Audience control. The Winning Team era isn’t about literature; it’s about logistics. Premium SKUs, signed plates, and direct fulfillment create a revenue stream that doubles as supporter engagement. That’s why the live signings, the limited editions, and the just-so price points matter—they combine fundraising logic with retail tactics. (Winning Team Publishing)
Ghosts in the machine: coauthors, credits, and conflicts
No Trump publishing saga would be complete without ghosts—ghostwriters, that is—and the occasional credit controversy. Schwartz’s regret tour in 2016 turned Art of the Deal into a referendum on authorship. Winning Team’s photo books revived authorship disputes from a different angle: not the words, but the images. Reports that Trump’s team asked Craighead to delay her own book (and even floated taking a cut of her advance in exchange for a foreword) before releasing Our Journey Together using many official White House photos show how power and publishing collide when your subject was the president. (TIME)
The frictions also explain why the traditional path collapsed. It wasn’t just internal politics at the big houses. Editors and executives fretted about the cost of fact-checking a mercurial narrator and the backlash among their own staffs. The “no deal” climate of 2021 made Winning Team less a vanity project than a necessity if more Trump books were going to exist on Trump’s terms. (Business Insider)
The pricing psychology
Even Trump’s sticker prices tell a story. Art of the Deal was an old-school hardcover phenomenon. The recent photo books, by contrast, often start around $75–$99—and up to $399 signed. That’s museum-gift-shop economics: a bundle of emotion, identity, and scarcity that pushes shoppers from “Should I read this?” to “Should I own this?” The Guardian flagged those price points for Letters to Trump; Winning Team’s storefront does the rest. (The Guardian)
The tactic works because it replaces the old discovery engine (bookstores, reviews, word of mouth) with a different funnel: rallies, email lists, social posts, and conservative media segments. The book stops being a mass-market commodity; it becomes merchandise with pages.
How the playbook evolved
If you zoom out, Trump’s publishing history falls into three acts:
Act I: Big-House Mythmaking (1987–2000). Random House and Times Books shaped a bestselling brand vehicle in Art of the Deal and cashed in on sequel demand through boom and bust. (Wikipedia)
Act II: Platform Synergy (2004–2011). TV fame fueled “how-to” titles and partnerships (Kiyosaki, Zanker) that turned seminars and celebrity into steady sales. (Wikipedia)
Act III: The Direct Model (2021–present). Shut out (or opting out) of the Big Five, Trumpworld built its own press, priced high, and sold direct—generating millions in royalties without ever blinking at the traditional memoir that New York publishing assumed would come next. (Wikipedia)
What gets lost—and what gets gained
Is anything sacrificed in the shift? If you wanted a deeply reported presidential memoir with rigorous citations and a steady editorial hand, you haven’t gotten it. Reviewers who panned Save America weren’t wrong about the design and the propaganda feel. And cutting out big-house editors means fewer brakes on error, embellishment, or score-settling captions. (Wikipedia)
But from a dealmaker’s perspective, the gains are obvious: speed, control, and margin. The audience that wants a Trump book in 2024 or 2025 doesn’t necessarily want 600 pages of policy introspection; they want artifacts, signatures, and a branded version of memory. On that metric, the direct model is a surgical hit.
The enduring lesson of the Trump shelf
The tidy moral of Art of the Deal was always that the deal precedes the product. In Trump’s publishing life, the deal is the product: the carefully split advance, the paperback auction, the TV-synced “how-to,” the $99 coffee-table book shipped from a warehouse you can control. That’s why the story of his books is also a story about where power sits in modern media—less in Lower Manhattan corner offices, more in the mailing lists and storefronts you own.
Four decades after he first put his name above a title, Trump’s most reliable book deal is the one he signs with his own readers. And for now, those readers keep paying—sometimes $99, sometimes $399, sometimes more—for the privilege of owning a piece of the brand.
Sources & Notes
- The Art of the Deal’s bestseller run (13 weeks at #1; 48 weeks total) and Random House publication; background on authorship and sales trajectory. (Wikipedia)
- Tony Schwartz’s 50/50 advance and royalty split; Trump legal demand for repayment; Schwartz’s later statements. (The Guardian)
- Continued Art of the Deal royalties noted in later disclosures and reporting. (Wikipedia)
- 1990’s Surviving at the Top print run and paperback retitle (The Art of Survival), plus its bestseller stint. (Wikipedia)
- The Art of the Comeback publication details (1997, Times Books). (Wikipedia)
- Trump: How to Get Rich and mid-2000s “how-to” cycle tied to The Apprentice. (Wikipedia)
- Why We Want You to Be Rich debuting at #1 and Trump/Kiyosaki collaboration. (Wikipedia)
- Think Big and Kick Ass 2007 printing and the $100-bill promo. (Wikipedia)
- Crippled America (Threshold Editions) and the signed-copy sales push. (Simon & Schuster)
- Publishers’ reluctance to a Trump memoir and the 2021 open letter. (Business Insider)
- Launch of Winning Team Publishing; its role as Trumpworld’s in-house press; airport bookseller refusal. (Wikipedia)
- Our Journey Together pricing via 45Books and controversy over White House photos/Shealah Craighead’s scuttled plan. (Winning Team Publishing)
- Royalties tallies: $5.75 million from Our Journey Together over 18 months. (Forbes)
- Letters to Trump price points ($99/$399). (The Guardian)
- Save America (2024) publication and reception context. (Wikipedia)
- Recent disclosure indicating millions from Winning Team Publishing. (Forbes)
MARK SOTOMAYOR 