The Caddy, the Document, and the Most Dangerous Sentence Donald Trump Has Ever Written
At just after midnight on June 18th, the President of the United States posted a two-page document on Truth Social comparing himself favorably to Hitler, Mao, Stalin, Napoleon, Genghis Khan, Attila the Hun, and Alexander the Great. He captioned it with five words:
“Presidential Historian Dave King — Sounds good to me!” 270toWin.com
Dave King is not a presidential historian. He is a 70-year-old wealthy South African, a non-college graduate, and Gary Player’s longtime caddy and personal confidant. He is not a professor. He has no academic credentials. He has no institutional standing. He is, to be precise, the man who carries the golf bag. PollingSource
King presented Trump with the two-page document during an event honoring Player, the Hall of Fame golfer who is now 90, and later explained his theory directly to Trump over golf in Florida. The document’s core argument was straightforward flattery dressed up in the language of geopolitics: Alexander the Great, the Caesars, Genghis Khan, Attila the Hun, Napoleon, Hitler, Mao, and Stalin all lacked “global reach.” Their power was “limited to restricted local areas.” Trump, by contrast, commands “modern logistics, manpower, technology, and global economic muscle.” PollingSourcePollingSource
Trump loved it. He proudly asked an aide to fetch a copy during his interview with Maggie Haberman and Jonathan Swan for their new book “Regime Change,” then began reading the names aloud, explaining how each historical figure “fell short of his own power as U.S. president.” He said of Alexander the Great, the Caesars, and William the Conqueror: “They didn’t have airplanes, right? You couldn’t travel around.” He said “Napoleon” — according to the authors — “with relish.” Race to the WHRace to the WH
And then — and this is the part that should stop you cold — he looked up from the list that included the architects of the Holocaust, the Gulag, and the Cultural Revolution, and said: “They maintained power through fear. Who would ever do a thing like that? Right?” Race to the WH
Who would ever do a thing like that.
This is the man who has sicced the FBI on political enemies. Who has weaponized the Justice Department against journalists, prosecutors, and judges. Who has used tariffs as a cudgel against nations that displease him and pardoned criminals who served his interests. Who has, by his own account to Axios following the Iran war, discovered “no limits” to his power. This man read a list that included Adolf Hitler and asked, rhetorically, who would ever maintain power through fear. 270toWin.com
The answer, of course, was sitting in the chair reading the list.
But let’s stay with the caddy for a moment, because it matters. Haberman and Swan write that the revealing part was not the document itself but “the evident pleasure he took in the company of Mao, Hitler, and Stalin” — and “the untroubled ease with which he accepted a place among men who had reshaped the world through conquest and fear.” There was no moral reckoning. No pause. No acknowledgment that six of the ten names on that list are synonymous with mass murder on a scale that defies comprehension. Just pleasure. Relish. The satisfied nod of a man who has finally found the right frame for how he sees himself. Race to the WH
And he got this from a golf caddy.
Not a historian. Not a scholar. Not a biographer or a political theorist or even a particularly credentialed observer of world affairs. A man who carries bags at tournaments. A man who, by his own account, immigrated to South Africa from Scotland in 1976 — at the height of the apartheid regime — and became wealthy enough to befriend one of golf’s legends. This is Trump’s idea of a presidential historian. This is the intellectual framework for how the sitting President of the United States understands his own power. PollingSource
“Sounds good to me.”
That caption is doing extraordinary work. It is simultaneously an endorsement, a confession, and a threat. He is telling you exactly who he thinks he is. He is telling you exactly what company he believes he belongs in. He is telling you that the moral catastrophes represented by those names on that list register to him only as data points about power — not as warnings, not as cautionary tales, not as the defining horrors of the modern era that shaped every institution and international norm designed to prevent their recurrence.
He sees Hitler and thinks: impressive reach, but limited by geography.
He sees Mao and thinks: formidable, but no social media.
He sees Stalin and thinks: close, but no nuclear arsenal pointed outward at the whole world.
And then he sees himself, and he thinks: yes. That’s the one.
The caddy told him what he wanted to hear. That’s what caddies do — they read the terrain, they hand you the right club, they tell you it’s a good shot. Dave King handed Donald Trump the most dangerous document in American political history: a permission slip. Two pages that told the most powerful man on earth that his power was not just legitimate but unprecedented, not just broad but total, not just American but global and historical and beyond any meaningful constraint.
And the President of the United States posted it on Truth Social at midnight and wrote four words underneath it.
Sounds good to me.
It should not sound good to any of us.