Kissinger did this.
From Kissinger: A Biography by Walter Isaacson:
Lord works for days on a report and submits it to Kissinger. Kissinger returns it with one question: “Is this the best you can do?” Lord takes it back, reworks it, resubmits. Kissinger returns it again. Same question. “Is this the best you can do?” This goes on — six, eight, maybe ten rounds. Finally, Lord brings back a draft and declares: “Damn it, yes, it’s the best I can do!”
Kissinger replies: “Fine, then I guess I’ll read it this time.”
Lord himself recalled the intensity, saying, “You’d have to go through about 20 drafts and many insults before you got the ultimate speech.”