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The Unconventional Literary Pursuits of Donald Trump

Prior to running for president, it’s tradition for the aspiring candidate to publish a sterile book as an autobiographical foundation for their bid. This spring, Ron DeSantis offered a multi-week bestseller titled The Courage to Be Free. Mike Pence inked So Help Me God last fall. Tim Scott’s America, A Redemption Story popped last August. Nikki Haley crafted two works in recent years. Vivek Ramaswamy has written three. If Asa Hutchinson has produced his life’s story, it’s not easily found on Amazon.

Then there’s Donald Trump. Of whom everything has seemingly been written, said, or alleged over the last decade. Trump respects the fact that the human brain processes images 60,000 times faster than text. So unlike the prose-heavy entries from his rivals, he’s turned his post-presidency literary efforts toward consumption-friendly coffee table books (minted by Sergio Gor, the MAGAverse’s publisher nonpareil).

His first pictorial, a 12″ x 10″ 4-pound opus of his time in the Oval Office called Our Journey Together, is believed to be the biggest post-presidency book in history. Much more impressive than Obama’s 768-page slog (which many bought, few read, and none enjoyed). Our Journey Together also sold extremely well, grossing more than $20 million with an initial print run of 200,000 copies. Trump cites the blockbuster success as motivation for his second release, a compilation whose focus provides viewers with cocktail party trivia fodder: What do Princess Diana, Dale Earnhardt, and Roy Cohn have in common?

Besides the obvious (RIP), the trio were all pen pals with the famed New York businessman, of course! Their notes are showcased in the recently published Letters to Trump, a fascinating catalog of private correspondence, both consequential and trivial in nature, between hundreds of public figures and The Donald from the 1980s through the present.

The former president’s affection for communicating on social media is well known. This new volume reveals the extent of his prodigious epistolarian tendencies in the Paleolithic pre-social media world. The release of this partial personal archive with leaders in government, media, sports, and entertainment adds a degree of depth and unique historical context to our understanding of Trump’s celebrity factor that he leveraged to reach the White House.

The codex is mainly formatted like this: a copy of a letter to (or from) Trump to a famous person and a picture of Trump with the subject accompanied by “strong statements about individuals the world wants to hear about.” Recurring puckish prompts and unique syntax leave little doubt that he is responsible for every word in the book.

For presidential scholars, there’s relevant material between the mogul and his Republican predecessors. The collection opens with a prophetic 1987 letter from Richard Nixon that proudly declares his wife Pat to be an “expert on politics and she predicts that whenever you decide to run for office you will be a winner!” Ronald Reagan sends his regards for leadership in supporting “the Foundation for the Commemoration of the United States Constitution.” Gratitude for hosting a fundraiser for Jeb doesn’t spare George H.W. Bush from captioned mockery. Then-governor George W. Bush’s documented regret for being unable to attend a Miss Teen USA event (hosted in South Padre, Texas) also makes the cut.

For those too young to remember the 1980s, there’s an interesting cultural nugget: Phil Donahue was appointment viewing—at least for the first ladies. The “very nice” Barbara Bush was compelled to mail a brief, handwritten card: “As I was leaving the house this morning I heard you being attacked by Phil Donahue. You were wonderful!” A Nixon letter begins with a comment on a different appearance: “I did not see the program, but Mrs. Nixon told me that you were great on the Donahue Show.” Nowadays, effortful correspondence like this has been reduced to casual text messaging.

Leading Democrats are well represented. Ted Kennedy’s appreciation for “warm hospitality” and transportation is on display. Trump allows that he knew the Massachusetts senator and Chappaquiddick survivor “very well” thanks to their mutual “relationship to Palm Beach” and offers a mysterious boast: “I helped him with something important and confidential to him and his family … and he never forgot it.” Former San Francisco mayor Willie Brown and The Donald apparently shared an emergency helicopter landing together. Space is reserved to spotlight Brown’s “very interesting” relationship with Kamala Harris. And, of course: the Clintons. One letter is paired with the troll-tastic photo of giddy Bill with Monica Lewinsky, while one of the captions says of Bubba: “I liked him and he liked me, and neither of us liked Hillary (just kidding).” The narrator gets candid on the page dedicated to his defeated nemesis: “Whether we like it or not, Hillary is very smart and very tough, and she’s been through a lot in so many ways.” This prefaces the portion where his tabloid instincts tap in: “After the election, she was the angriest woman anywhere in the world—because she saw what happened in 2020, she would tell anyone who listened, ‘Why the hell wouldn’t they cheat for me in 2016 like they did for Joe Biden in 2020?’”

Foreign dignitaries receive ample attention. A 1995 note from then-Prince Charles reminds readers that Trump lives by a “shooters shoot” mentality, as the topic of the royal’s note is an acknowledgment of an invitation to join the “very splendid” Mar-a-Lago Club. And there’s a trove of official communiqués from heads of state: Vladimir Putin, Viktor Orban, Xi Jinping, Emmanuel Macron, Andres Manuel Lopez Obrador, Jair Bolsonaro, Kim Jong-Un, and more.

Hollywood A-listers get heavy action. Jack Nicholson, Clint Eastwood, Regis Philbin, Tony Bennett, Jay Leno, Oprah, George Lucas, and Michael Jackson are just a few of the iconic pen pals. There’s a corny birthday one-liner sent to Sean Connery and a punchy assessment on Alec Baldwin’s lethal episode on the set of Rust. The author lets us know that he is friends with Shaquille O’Neal, who needed extra leg room “despite the large tables” at Trump’s wedding. This reviewer was relieved to read that Shaq is “doing really well.”

Like any proper campaign season book, it concludes by citing previous victories to credential future endeavors. The most substantive piece in the coda is a 2023 memo penned by Robert C. O’Brien, former national security adviser and international hostage negotiator sui generis. After highlighting a register of foreign policy achievements, O’Brien ends with a biblical reference: “In his Sermon on the Mount, Jesus said, ‘blessed are the peacemakers, for they shall be sons of God.’ Such will be the legacy of the Trump Administration.” In a world plagued by chaos, “peacemaker” will almost certainly be a theme Trump pushes on the stump.

Letters to Trump calls to mind the adage, “a picture is worth a thousand words.” Which makes it metaphorically as comprehensive as a 320,000-word work. Trump’s coffee table books are expensive (list price $99!) but sell well because they are informative, entertaining, and simple in their messaging. When he’s at his political best, he sticks to that tridental construct. Hillary had bland white paper proposals; Trump campaigned on a “big, beautiful wall.” This book, like his successful 2016 campaign, proves you can say a lot while keeping your messages vivid and concise (a concept that the industry now refers to by the trademarked term “Smart Brevity”). All politicians would be wise to master this art if they like selling books, winning elections—or convincing a jury to acquit.

Letters to Trump
by Donald J. Trump
Winning Team, 320 pp., $99

Rob Lockwood is a media strategist who resides in the Washington, D.C., area.