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This paper starts from the connection between hypothetical reasoning and juridical reasoning in Leibniz’s writings from the period of his youth. Hypothetical conditionals in Leibniz’s mature logic of possible worlds, and some elements of divergence and convergence between these different steps in the development of Leibniz’s logic, will be then considered. Some difficult aspects in Leibniz’s theory of counterfactuals will be analyzed in comparison to some elements of David Lewis’ possible worlds logic. In conclusion, it will be suggested that, in certain aspects of Leibniz’s mature logic of counterfactuals, some basic features of his juridical approach are preserved.