The article examines the rhetorical legacy of Marcus Tullius Cicero as a methodological foundation for contemporary legal research in an era of transformations. It is substantiated that the principles of ancient rhetoric the hermeneutic presupposition and the cognitive-linguistic mechanisms of understanding law retain their relevance during the transition of states to new socio-technological orders. Using the transitional period from the Roman Republic to the Empire as material, the article demonstrates how subjectivism in lawmaking and judicial discretion leads to “norm arbitrariness” and “judicial arbitrariness,” which undermine justice and the predictability of law. A futurological concept is proposed a “symbiosis” between human legal thought and artificial intelligence: the integration of AI into lawmaking and adjudication based on the philosophical doctrines of Stoicism, the rhetoric of Cicero, the ideas of Plato and Aristotle on the supremacy of law, and Ayn Rand’s views on protecting the rights of the individual creator. It is emphasized that only by relying on the logic, humanism, and objectivity laid down by ancient thinkers can AI be programmed to overcome subjective distortions in law and to create an anti-fragile, resilient legal system. The article provides forecasts on how the integration of philosophy and AI can strengthen the rule of law, ensure judicial independence, protect private property, and stabilize rules for economic prosperity, turning lawyers into “architects” of the state of the future. The article is intended for legal theorists, historians of legal doctrines, and specialists in legal technologies interested in the evolution of legal institutions and the influence of AI on law.