Interest in relationships between the local dimensions of political ideology, behavior, and culture has increased in recent years. Tolerance can be understood to have two dimensions: (1) substantive, meaning the types of diversity in a community and resident relationships within that diversity; and (2) procedural, relating to how tolerance is operationalized by researchers. This research addresses both the substantive and procedural aspects of tolerance in three communities using a nested methodology, including case studies, interviews with local officials, and citizen surveys. It concludes that cities with greater diversity are not consistently more tolerant, and much depends on the definition of tolerance employed. There is no magic or necessary connection between a diverse and tolerant citizenry. Local history colors how diversity and tolerance interact; development patterns that separate residents by race, ethnicity, or income appear to leave legacies that are difficult to overcome.