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This paper reflects my address as IAAIL president at ICAIL 2021. It is aimed to give my vision of the status of the AI and Law discipline, and possible future perspectives. In this respect, I go through different seasons of AI research (of AI and Law in particular): from the Winter of AI, namely a period of mistrust in AI (throughout the eighties until early nineties), to the Summer of AI, namely the current period of great interest in the discipline with lots of expectations. One of the results of the first decades of AI research is that “intelligence requires knowledge”. Since its inception the Web proved to be an extraordinary vehicle for knowledge creation and sharing, therefore it’s not a surprise if the evolution of AI has followed the evolution of the Web. I argue that a bottom-up approach, in terms of machine/deep learning and NLP to extract knowledge from raw data, combined with a top-down approach, in terms of legal knowledge representation and models for legal reasoning and argumentation, may represent a promotion for the development of the Semantic Web, as well as of AI systems. Finally, I provide my insight in the potential of AI development, which takes into account technological opportunities and theoretical limits.

The winter, the summer and the summer dream of artificial intelligence in law