This chapter explores the personality and behavior of Charles-Maurice de Talleyrand-Périgord, the French diplomat and negotiator at the turn of the eighteenth and nineteenth centuries. Talleyrand managed to save France from annihilation after the defeats of Napoleon, and his diplomacy helped compensate for military failure. Talleyrand’s skill in foreseeing problems and dealing with them at the right moment contains many lessons for modern diplomacy, not least on how to effectively negotiate in the public international arena. This chapter looks at the tactics and strategies he used and draws lessons from the way he dealt with international politics. It also shows that politicians often ignore diplomatic advice to their own detriment. Paradoxically, Napoleon’s genius for war meant his empire’s destruction, and it was Talleyrand who told him not to be so greedy and to stop at the opportune moment. Napoleon did not stop; today, we may ask the question: will Vladimir Putin stop? Undoubtedly, a price will be paid, and unfortunately, although it is sometimes possible to learn from history, all too often, it is not. This chapter aspires to draw helpful lessons for those who do want to apply them in their own interest, the interests of their country, and the global interest.