This Element investigates the process of executive aggrandizement to identify factors associated with democratic resilience. We focus on five democracies that showed resilience in the face of incumbent-led autocratization. To understand how these cases survived, we pair them with similar cases where incumbents successfully dismantled democracy from within. Through structured focused comparisons, our inductive exercise provides insights into how the process of executive aggrandizement unfolds. The case narratives reveal similar patterns, with incumbents often targeting the media, civil society, and judiciary and using shared tactics to weaken democratic institutions. Where democracies survived, anti-democratic incumbents made critical errors, including major policy blunders and miscalculations, which ultimately cost them their positions and allowed democracy to rebound. Where democracy broke down, incumbents were largely able to avoid or mitigate such errors, often through ethnopopulist appeals. This Element investigates democratic resilience and breakdown from 1900 to 2022, based on global data and qualitative case study evidence.