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The foundation of Machiavellian philosophy and its deepest insight is a sense of proportion. It corresponds to the Grotian apprehension of the moral complexity of politics… This is the special picture of political life one gets from reading Machiavelli himself and ‘irony’ is a category of philosophical Machiavellians. The word is not, I think, found in Machiavelli, but political irony is in fact what he very lovingly studied. Irony is a Machiavellian category while tragedy is a Grotian category. ‘Tragedy’ implies a standpoint outside the political drama, in which we experience, for example, admiration for Othello's nobility, pity for his weakness, and terror at Iago's wickedness… Now, it is difficult to adopt a tragic standpoint about politics, because ‘politics’ implies a situation in which we are still involved, where we can still act and affect the outcome, and anyway where we do not know the outcome because the drama is unfinished. To become fully tragic, politics have to be dead politics, that is, history: the tragedy of Athens, and of the League of Nations…
Irony is, so to speak, the factual skeleton of tragedy, stripped of its moral and transcendental clothing. In literature it is the warping of a statement by its context; a character means one thing by a statement but we know the context and outcome that he does not, and see it has a different meaning. As Banquo rides away to be murdered, as Macbeth has arranged, Macbeth says to him genially: ‘Fail not our feast’—‘My lord, I will not.’ This is Sophoclean irony and there are other kinds, more complex. Irony can be seen in politics when statesmen pursue ends that recoil upon them, and turn into their opposites. Hugh R. Wilson, in Diplomat between Wars, says that the policy of the USA was of ‘overwhelming importance’ to the League of Nations in the Manchurian crisis, which makes ironic America's fear of, commitment and involvement: however little she wanted to be committed she was certainly involved, and by refusing to commit herself at that time she made her involvement in the struggle with Japan all the more certain. It is equally ironical that Britain and France went to war in 1939 to restore the balance of power in Europe by destroying Nazi Germany, embraced the Soviet alliance for that purpose, and ended with Europe as badly unbalanced by Stalin's power as it had been by Hitler's.
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Martin Wight (Four Seminal Thinkers in International Theory: Machiavelli, Grotius, Kant, and Mazzini)