The myth of “tough love” leadership emerges in cultural narratives as a superior approach to improving students’ educational opportunities in urban schools facing challenging circumstances. This model, however, has not been conceptualized, and consequently, empirical research about it is lacking. We formulated a typology of tough love leadership as a mix of four behaviors that combine “tough” and “loving” approaches, with a focus on crisis management and a positive school vision. The study used the tough love leadership conceptualization to explore different mixes of tough love leadership, manifesting in four urban schools facing challenging circumstances. The study’s implications are discussed.