On January 14, 2009, incoming president Barack Obama ventured to the home of George Will to have dinner with a group of right-wing luminaries including Charles Krauthammer, William Kristol, Larry Kudlow, David Brooks, Rich Lowry, Peggy Noonan, Michael Barone, and Paul Gigot. Every one of those figures opposed essentially every single one of Obama’s major policies, both during the preceding campaign and during the two terms that followed, frequently in hysterical and paranoid terms.
Why, then, would Obama even bother? Because he believed there was a certain value in bouncing his ideas off the conservative opposition, probing his own thought for weaknesses, and searching for useful points to take from the opposing side.
The merits (or lack thereof) of listening to conservative opinion has become a point of contention and angst among liberal journalists. Staffers at the New York Times and The Atlantic have both held gripe sessions, which leaked publicly, to air internal complaints about their conservative columnists. (Both have right-of-center voices, and the Atlantic hired and immediately fired right-wing provocateur Kevin Williamson.) Meanwhile, some of the smarter liberal writers, like Dave Roberts and Brian Beutler, have argued that liberal media should give up its attempts to represent conservatives on the op-ed page. Their case reflects the renewed belief on the left, which has understandably gained force from the election of Trump, that exposing liberal or mainstream news audiences to conservative argument has no value at all.