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This paper explores cases of executive aggrandizement during the tenure of executives who are elected to serve more than one term. We examine three categories of executives: 1) those who engage in executive aggrandizement during their first term and continue to do so in subsequent terms (repeat offenders), 2) those who do not engage in backsliding during their first term but begin to do so in later terms (second-wind saboteurs), and 3) those who engage in backsliding during their first term but not in subsequent terms (reformed offenders). Through a comparative analysis of over 200 leaders, we investigate how patterns of executive aggrandizement vary across the categories and what consequences these processes have for democracy. Our findings offer critical insights for safeguarding democratic institutions, particularly in systems where executives face the prospect of multiple terms in office.