The relationship between the presidency and the press has transformed--seemingly overnight--from one where reports and columns were filed, edited, and deliberated for hours before publication into a brave new world where texts, tweets, and sound bites race from composition to release within a matter of seconds. This change, which has ultimately made political journalism both more open and more difficult, brings about many questions, but perhaps the two most important are these: Are the hard questions still being asked? Are they still being answered?

In Columns to Characters,...