The moment I remember was when an NBC reporter gave him a textbook softball question: "What do you say to Americans who are scared?". It's a question that any former President or any other world leader would instantly recognize as teeing him up for an inspiring and reassuring speech about Nationhood and courage whilst working in talking points about social distancing, masks, and reaffirming any recent positive news about vaccine development.
His actual reply: "I’d Say That You’re A Terrible Reporter."