However, if Saturday night is any indication, were Trump to swap his role as commander-in-chief for comedian-in-chief, he would likely be a cruel, heartless comedian who would "punch down", mocking those already struggling.
Trump took the opportunity to boast about his comedic strengths, especially in the field of self-deprecating humor. On Attorney General Jeff Sessions, the president said, "I offered him a ride over and he recused himself". "That's why I accepted".
Since its foundation in 1855, nearly every president has attended the annual white tie dinner at least once during their administration.
This is the first time that Trump attended the Gridiron Club dinner, after skipping the two dinners held past year.
In remarks released ahead of the event, the club's president, David Lightman, congressional editor for McClatchy News, assured the president that the crowd was "way bigger than Cleveland's".
But it might be too late, he said, for "print media".
Members of the Washington press corps are sharpening their wits for musical and rhetorical takedowns of President Donald Trump, Hillary Clinton, Barack Obama and others. "What are you going to do?"
He unloaded on familiar targets: the outgoing publisher of the "failing New York Times", CNN, House Democratic Leader Nancy Pelosi, "Sleepy Joe" Biden, Oprah Winfrey (whose potential presidential run appears to have unsettled him), Rep. Adam Schiff of California and Sen. "She said, behave! By the way she has been an incredible first lady".
Toward the end of his comments, Trump couldn't resist some of his favorite themes, revisiting his election night victory and chiding reporters to be fair.
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It was a measure of the uncertainty he creates that, when the president said he "won't rule out direct talks" with North Korea's Kim Jong Un, no one was really sure if he was serious.
Cotton made light of what he called the source of his personality: the common touch of Harvard, the sensitivity of the Army, and the personal touch of Dick Cheney. In fact, based on what was reported about the event (cameras were not permitted), I wish Trump would give up his "day job" and pursue comedy full time.
In the end, nothing really changed from an evening with a central goal, Music Chairman John Mulligan said, "to promote good fellowship" in the capital. He also observed, "No matter how many times we say it, we don't drain the swamps either". The charitable organization contributes to college scholarships and journalistic organizations with an evening of humorous give-and-take between the press and the people they cover.