Of the various topics that have occupied readers of Isaiah Berlin—liberty, pluralism, nationalism, Marxism, romanticism, to name just a few—very few have focused on the role of judgment in his philosophy.1 One possible reason for this is that the concept of judgment, unlike other concepts in the political-theory lexicon, seems too indistinct to permit careful analysis.2 Judgment often seems too circumstantial, too contextual, to have a theory of. What is good judgment in one situation will not be so in another. It consists, to a large degree, in our capacity to read the times, and I do not mean the New York Times. The concept of judgment is invariably connected to character, but good character seems as elusive as good judgment. Do certain kinds of people simply have good judgment and, if so, what are the characteristics that produce it? We seem to be caught in a vicious—or, should I say, virtuous—circle.