Fox News' Ari Fleischer likens Trump’s Greenland interest to King Henry VIII’s Scotland ambition
NEW YORK CITY, NEW YORK: Fox News contributor Ari Fleischer on Wednesday, January 21, compared President Donald Trump’s interest in acquiring Greenland to how King Henry VIII tried to take over Scotland in the 1500s.
Although Trump has not shared specifics, he claims to have a "concept of a deal" to take control of the island from Denmark.
Fleischer links Trump strategy to sixteenth century
Fleischer, while appearing on Fox Business’ Kudlow, explained that history is repeating itself in a way, pointing back to the 16th century.
He noted that there is a historical analogy to Trump's overtures towards Greenland and referenced King Henry VIII’s "Rough Wooing" of Scotland.
He explained that the English King wanted Scotland the same way Donald Trump wants Greenland.
In that instance, King Henry VIII tried to force a marriage between his son and Mary, Queen of Scots, but when the Scottish people refused, he sent in his army.
Fleischer suggested that Trump is using a softer version of this pressure tactic, saying, “I think President Trump and Greenland, a little more woo, a little less rough. And he’ll get there.”
Trump just pulled a classic “bull in the china shop” move on Greenland and the world took the bait.
— Overton (@overton_news) January 21, 2026
The blueprint was lifted right from the pages of his own book, The Art of the Deal.
Fox News’ Ari Fleischer broke down the strategy:
“Now, there’s so much to be defined here,… pic.twitter.com/BbJrwBr6QE
Trump's pressure tactics on Greenland have involved escalating tariff threats, military rhetoric, and public ultimatums to coerce Denmark and the North Atlantic Treaty Organization (NATO) allies into concessions.
While the US already has military rights in Greenland due to a 1951 agreement, Trump is pushing for full ownership.
Fleischer analyses Trump’s art of the deal
The president discussed his goals while attending a meeting in Davos, telling CNBC, “I think it’s going to be a very good deal for the United States and also for them, and we’re going to work together with something to do with the Arctic as a whole, but also Greenland.”
Fleischer said a classic move by Trump is when he acts like a "bull in the china shop" to startle people.
He explained that Trump makes everyone nervous about what he might do, and then he “declares a fait accompli, and they look like the bad guys for getting in the way of the fait accompli that he declared today.”
Fleischer admitted he wasn't sure if this specific plan would succeed, but insisted that this aggressive approach is simply how the president operates.
World leaders seek Trump despite criticism
Even though European leaders have been critical of the president, host, Larry Kudlow noted that they still seem eager to talk to him.
Kudlow called the situation "funny" and "kinda cool," pointing out that despite the mean things they said about Trump, world leaders still rushed to meet with him in Davos.
