But Trump’s winking stance, jarring and inconsonant though it may be with the rest of liberals’ conception of him, is one of the essential, even primal ways the president keeps his base on board, laughing along. For Trump and his defenders, a little gentle self-mocking does more than just warm up a room. It can neutralize his opponents’ attacks. And it can let Trump off the hook even when he probably isn’t joking, as when Marco Rubio argued last month that Trump was only kidding when he declared that China should investigate Hunter Biden.
But it’s most powerful when it makes his supporters feel that they’re in on Trump’s jokes in a way the establishment isn’t. In a sense, this effect is an extension of the 2016 campaign formulation, likely coined by GOP strategist Brad Todd and popularized by Peter Thiel, that Trump’s supporters “take him seriously, but not literally.” Because Trump’s fans take him seriously, they recognize when he isn’t being serious, and laugh when his opponents miss the joke. In the same way “Fox and Friends” can make viewers feel as if they’re part of a knowing club, Trump’s jokes give his supporters a way to feel superior to the elites, to mock what they see as a humorless and predictable political establishment. After Trump’s Greenland tweet, one fan on Twitter captured that feeling: “I can picture President Trump sitting in the OVAL, after a productive day, chuckling as he tweets to trigger the left. BEST POTUS EVER!”
This split-screen reaction to Trump’s jokes—fans seeing a twinkle in his eye, opponents seeing creeping authoritarianism—happens offline, too.