Trump Time Capsule #146: Al Smith Dinner

“Light” events are some of the heaviest lifting in political life. Comedy is hard to begin with, and for the kinds of people involved in politics, jokes are vastly more difficult to write or deliver than “substantive” remarks. And for presidents or presidential aspirants, we’re talking about a special kind of joke. These eminent figures need to come across as “modest” and self-deprecatory, but only up to a humble-brag point. (That is, just enough so the audience and reviewers will say, “Oh, isn’t it charming that he’s willing to laugh at himself!”) Real comedy often includes a “what the hell!” willingness to say something that will genuinely shock or offend, which national politicians can’t afford to do. The White House Correspondents Dinner, the Gridiron, the Al Smith Dinner—any event like this is hard (as David Litt, a former member of the Obama speechwriting team, explains in a very nice item just now).