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In Book IV of his Politics, Aristotle famously declares that the best “possible” regime is one built upon a strong middling element, or what contemporary readers understand as the middle class. Initially, this claim may seem puzzling; Aristotle’s affection for the middling element, with its “middling” level of virtue, appears inconsistent with the emphasis he places on virtue elsewhere in the text, along with his characterization of virtue as an "extreme" in the Nicomachean Ethics. Yet while the middling regime may appear un-Aristotelian at first glance, I argue it is key to understanding Aristotle’s conception of the regime more broadly. In particular, his presentation of the middling regime as distinct from polity reveals the importance of having a ruling element characterized by equality and similarity, specifically a similar way of life and level of virtue. For Aristotle, I argue, different ways of life arise from the pursuit of different paths to happiness, and similarity in this domain facilitates affection and may even preserve the community’s status as polis.