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All elites in autocracies try to show loyalty to the autocrat to avoid punishment. However, not all behave as outright sycophants, and not all ‘yes-men’ pander to the ruler to the same degree. Why not? Building on social psychological research on ingratiation strategies and studies on personality cults, we argue that: i) ‘playing the sycophant’s card’ is a strategy that mainly weaker elites, more dependent on the autocrat, resort to; and ii) weaker elites that use this strategy are indeed rewarded for their public subordination. To test these hypotheses, we employ a novel empirical approach for observing and measuring elite loyalty in autocracies. Using text-as-data methods, we analyze original data on almost 1000 annual addresses of Russian governors to regional parliaments from 2007 to 2021. We find that governors up for election/reappointment and those more dependent on transfers from the center are indeed more likely to praise President Putin in their speeches and also tend to emphasize the same kind of topics and words as him. We also show that Putin’s ‘yes-men’ survive longer in office and receive more perks. The study improves our understanding of ruler-elite relations and the emergence of personality cults in autocracies.